Organic C CCCC CCCC

Catholic Junior College
H2 Chemistry 9647
2014 JC2 MYE Topical

Revision Package 1
Contents
Page
1.
Arenes
. 1
2.
Reaction
Kinetics
. 9
3.
Halogen
Derivatives
.. 22
4.
Hydroxy
Compounds
. 31
5.
Carbonyl
Compounds
46
6.
Carboxylic Acids & Derivatives
.. 63
7.
Nitrogen
Compounds
.. 80
8. Group II
.. 99
Arenes
QUESTIONS
Name: _________________________________________
Class: 2T____
Arenes
1. Arenes
1. Which of the following sequences of bromination, nitration and oxidation is expected to give the
best yield for synthesis of 2-bromo-4-nitrobenzoic acid from methylbenzene?
A
bromination, nitration, oxidation
B
bromination, oxidation, nitration
C
nitration, oxidation, bromination
D
nitration, bromination, oxidation
[PJC H2 2013 / Q24]
2. When benzene reacts with bromine in the presence of iron (III) bromide, what is the type of
reaction?
A
Electrophilic substitution
B
Electrophilic addition
C
Free radical substitution
D
Free radical addition
[IJC H2 2013 / Q19]
3. Which compound cannot be made directly from methylbenzene?
A
CH3
B
CH2Cl
Cl
C
CH3
D
CO2H
Br
[AJC H2 2012 / Q20]

4. Which property does benzene have as a consequence of the delocalised electrons present in its
molecule?
A
Addition reactions of benzene take place more easily than substitution.
B
Benzene is a good conductor of electricity.
C
Substitution in benzene takes place at one particular carbon atom.
D
The carboncarbon bond lengths are between those of CC bonds and C=C bonds.
[DHS H2 2011 / Q21]
5. Which property of benzene results from the stability associated with the ring of delocalized
electron cloud?
A
It does not conduct electricity.
B
It is susceptible to attack by electrophiles.
C
It undergoes electrophilic substitution instead of electrophilic addition.
D
All the carbon-carbon bonds have exactly the same bond length.
[MJC H2 2011 / Q18]
6. During the halogenation of benzene, a chlorine electrophile substitutes at a carbon atom. Which
one of the following gives the arrangement of the bonds at this carbon atom during the reaction?
Arenes
at the start of the

reaction
planar
planar
planar
tetrahedral
A
B
C
D
in the intermediate
complex
planar
tetrahedral
tetrahedral
planar
at the end of the

reaction
planar
tetrahedral
planar
planar
[TPJC H2 2011 / Q22]
7. Chlorine gas was heated with 1,3-dinitrobenzene in the presence of iron (III) chloride.
NO 2
NO2
The structure of the product of the reaction is

NO 2
Cl
Cl
Cl
NO2
Cl
NO 2
NO 2
C
Cl
NO 2
Cl
NO 2
D
Cl
NO 2
Cl
NO2
Cl
[MI H2 2011 / Q22]
8. When compound W was heated with acidified KMnO 4, compound X was obtained.
Arenes
Which of the following could be the structure of X?

A
OH
OH
OH
OH
O
O
OH
OH
O
[HCI 2012 / Q16]

9. Which synthesis readily yields the product shown?
A
30 oC
D
[HCI 2012 / Q17]
Structured Questions
Arenes
1.
(a)
Complete the reaction scheme below by drawing the structures of the organic compounds
in the boxes provided.
CH3
C
CH3
step III
limited Cl2, uv light
CH3
CH2Cl
CH3
Cl
step I
CH3
or
step IV
CH2
CH3
C
CH3
CH3
H
NO 2
step V
step II
Br2(aq),
room
temperature
CH2Br
COOH
CH3
OH
NO2
(b)
Suggest reagents and conditions for steps I and II by completing the table below.
(c)
Outline the mechanism of the reaction of step V.

Illustrate the mechanism stated by writing suitable equations, showing clearly the structure
of reaction intermediate, and using curly arrows to show the movement of electrons.
[PJC/2013/ Q5]
2. The molecule of benzene is a regular hexagon in which the electrons are described as being
delocalized.
(i) By using benzene as an example, explain, with the aid of a diagram, what is meant by the term
delocalized electrons in benzene.
(ii) Give one physical and one chemical property which arise due to this structure.
[MI H1 / IIB / Q1a]
3. Suggest one simple chemical test which would

enable you to distinguish the following pairs of
CH2CH3
CH2CH3
Arenes
compounds. State reagent(s) and condition(s) and

their corresponding observations.
[TPJC H1 / IIA / Q7a]
4. Benzyl chloride can undergo different types of reaction depending on the reagent and conditions
used. One of these reactions is used to convert benzyl chloride to 4-nitrobenzylchloride.
4-nitrobenzylchloride
State and describe the mechanism undergone during the conversion shown above.
[IJC 10/ II / Q4b]
Compound E, 2-methylbenzoic acid, is used as an intermediate for the synthesis of dyes and
pesticides.
5.
C
OH
C
OH
CH3
CH3
Compound E
Br
Compound F
Compound F can be formed when compound E undergoes bromination.

(i)
State the reagents and conditions for the reaction.
(ii)
Another product, which is the isomer of compound F, is also formed in the reaction. Draw the
displayed formula of the product.
(iii)
Name the type of reaction and describe the mechanism for this reaction, including curly arrows
showing the movement of electrons, and all charges.
[TJC 12/ III / Q2c]
6. A hydrocarbon, Z, has the molecular formula, C8H10. It reacts with chlorine either in the presence of
uv light or in the presence of AlCl3.
Arenes
(a) Draw an isomer of Z which upon reaction with chlorine forms a monosubstituted product
capable of rotating plane of polarised light.
(b) One possible isomer of Z is 1,3-dimethylbenzene.
(i) Suggest the reagents and conditions for a reaction that could be used to distinguish between
1,3-dimethylbenzene and your answer in (a). You should describe what you will see for each
compound.
(ii)Suggest the structure of the mononitrated product which is most likely to be formed when
1,3-dimethylbenzene reacts with concentrated nitric acid.
[CJC 12/ CA/ Q2]
7.
The benzene ring usually resists chemical oxidation but the process may be accomplished
microbiologically. The bacterium Pseudomonas putida in the presence of air rapidly converts
benzene into compound R.
(a)
Using the [O] notation for the oxidation of organic compounds, write a balanced equation for
this oxidation.
(b)
Is compound R optically active? Explain why.
(c)
In the structure of compound R, the two OH groups are on the same side of the plane of
the ring, i.e. the OH groups are in a cis arrangement.
Compound S is a trans isomer of compound R.
Draw the structure of compound S, showing clearly the trans arrangement.
[HCI 12/ II/ Q4(a)]
8.
Methylbenzene is also used to synthesize trinitrotoluene, TNT, according to the synthetic

CH3
CH
CH3
CH3
scheme 3below.
Step 1
NO2
NO2
Step 2
NO2
Step 3
O2 N
NO2
NO2
TNT
(C7H5N3O6)
Arenes
(i)
Suggest reagents and conditions for Step 1.
(ii)
Name the type of reaction and describe the mechanism for Step 1, including curly arrows showing
the movement of electrons, and all charges.
(iii)
Explain why compound A occurs in very small amounts in the products of Step 2.
CH3
NO2
O2N
A
(iv)
Explain why more rigorous conditions are necessary for Step 3 compared to Step 2.
[HCI 12/ III/ Q2(b)]
Halogen Derivatives
3. Halogen
1 1 mole of an organic compound P undergoes elimination on reaction with ethanolic sodium
hydroxide to form 2 moles of HBr. What could P be?
A
[AJC / MCQ / Q23]

2 1-bromopropane can be converted to 2-bromopropane in the reaction scheme below.
Which set of reagents for step I and step II would be most suitable?
Step I
Step II
A Hot aqueous KOH
PBr3
B Hot KOH in ethanol
HBr
C Hot concentrated H2SO4
Aqueous bromine
D Hydrogen gas with nickel catalyst
Bromine in the presence of ultraviolet light
[AJC H1 / MCQ / Q21]
3 Experiments are carried out on three compounds,
P, Q and R. A sample of 0.01 mol of each compound H
is refluxed with 40 cm3 of 1 mol dm-3 of NaOH
(in excess). Excess aqueous silver nitrate is added
to the resulting mixture after acidification in each case
and the mass of the precipitate weighed. What is the
mass in grams, of the precipitate formed by each
compound?
P
Q
R
A
4.31
4.31
4.31
B
2.87
2.87
1.44
C
2.87
4.31
1.44
D
1.44
4.31
1.44
Cl
C
H
Cl
Cl
Cl
Cl
Cl
H
Cl
Cl
Cl
[ACJC / MCQ / Q22]

4 A suspension of 1,3,4-trichlorocyclohexane is stirred in aqueous sodium hydroxide. How many
of the chlorine atoms in each molecule will be removed by hydrolysis?
A 0
B 1
C 2
D 3
[ACJC H1 / MCQ / Q21]
Halogen Derivatives
5 Which of the following statements best explains why fluoroalkanes are the least reactive
halogenoalkanes?
A Fluorine is much more electronegative than carbon.
B The F ion is the most stable halide ion.
C The CF bond is the most polar carbonhalogen bond.
D The CF bond is the strongest carbonhalogen bond.
[HCI / MCQ / Q25]
[HCI H1 / MCQ / Q24]
6 2,4,6-trinitrophenyl derivatives are bright yellow crystalline compounds that can be formed by
the following reaction.
The type of reaction mechanism shown above is

A Electrophilic substitution
C Nucleophilic substitution
B Electrophilic addition
D Nucleophilic addition
[IJC / MCQ / Q10]
7 Which one of the following, in alcoholic solution, produces a precipitate most rapidly when
warmed with aqueous silver nitrate?
A 1-chlorobutane
B 1-bromobutane
C 1-iodobutane
D chlorobenzene
[MI / MCQ / Q23]
8 Hydrogen bonding is not present in
A CH3Cl
B CH3NHCH3
C6H5OH
D C6H5COOH
[MI / MCQ / Q27]
9 A halogen compound S was boiled under reflux for some time with aqueous sodium hydroxide.
The resulting mixture was cooled, treated with dilute nitric acid, followed by the addition of
aqueous silver nitrate. No yellow precipitate was seen. Which one of the following could be
S?
[MI H1 / MCQ / Q16]

10 The following shows the Sandmeyer reaction to
produce iodobenzene from phenylamine. What
type of reaction is involved in step 2?
A Free radical substitution B Electrophilic substitution
C Nucleophilic substitution D Elimination
[NJC / MCQ / Q22]
Halogen Derivatives
11 Which one of the following compounds gives the greatest number of alkenes when it is reacted
with hot alcoholic potassium hydroxide?
A
B
[NJC H1 / MCQ / Q20]

12 In the Wurtz reaction, two halogenoalkanes react with sodium metal to form a new carboncarbon bond, resulting in the formation of a new alkane:
RX + R'X + 2Na
RR' + 2NaX
Which of the following does not show the correct product when the stated reactants are
reacted together in a Wurtz reaction?
A
CH3Br + C2H5I + 2Na
Br
CH3
CH3CH2CH3 + NaBr + NaI
CH3
2Na
2NaBr
Br
Cl
2Na
NaCl
NaBr
Br
D
Br
CH2Br
2Na
2NaBr
[SRJC 2011 / MCQ / Q24]

13 What is the product of a nucleophilic substitution reaction between 2-iodobutane and sodium
ethoxide (CH3CH2O Na+)?
A CH3CH=CHCH3
B CH3CH2 CH(OCH3)CH2CH3
C CH3CH2 CH(CH3)OCH2CH3
D (CH3 )2CHCH2 OCH2CH3
[NYJC / MCQ / Q22]
14 Some chlorobutanes were separately treated with hot ethanolic sodium hydroxide. Two of
these gave the same hydrocarbon, C4H6.
From which pair of chlorobutanes was this hydrocarbon obtained?
A CH3CH2CH2CH2Cl and CH3CH2CH2CHCl2
B CH3CHClCHClCH3 and ClCH2CH2CH2CH2Cl
C CH3CHClCH2CH3 and ClCH2CH2CH2CH2Cl
D CH3CCl2CH2CH3 and ClCH2CH2CH2CH3
[NYJC / MCQ / Q23]
Halogen Derivatives
15 Which of the following halides will react most rapidly with aqueous sodium hydroxide?
A (CH3)3CI
B (CH3)3CBr
C (CH3)3CCl
D (CH3)3CF
[NYJC H1 / MCQ / Q17]
16 Organic compound X undergone the following successive reactions:
I reaction with hydrogen chloride
II boiling with aqueous sodium hydroxide
III reaction with hot concentrated phosphoric acid
The final organic product was ethene. Which of the following could most likely be compound X?
A Ethene
B Ethanol
C Chloroethane
D Ethanoic acid
[SRJC / MCQ / Q24]
[SRJC H1 / MCQ / Q19]
17 In the upper atmosphere, chlorofluoroalkanes (CFCs) are broken down to give chlorine but not
fluorine radicals. What is the best explanation for this?
A Fluorine is more electronegative than chlorine.
B The C-F bond is longer than C-Cl bond.
C The C-F bond is stronger than C-Cl bond.
D The chlorine atom is larger than the fluorine atom.
18 In which of the following reactions is the inorganic reagent acting as a nucleophile?
A
Cl
Cl2
B
C
CH2=CH2
Cl2
+
CH2Cl
ClCH2CH2Cl
CH2I
KI
CH 3
HCl
KCl
HBr
CH 2Br
Br2
[TJC / MCQ / Q26]

19 When (chloromethyl)benzene, C6H5CH2Cl, is treated in succession with two reagents O and
P, it gives phenylethanoic acid, C 6H5CH2CO2H. Which of the following is a possible
combination for reagents O and P?
O
P
A NaOH (aq)
K2Cr2O7 (aq)
B Cl2 (aq)
NaOH (aq)
C HCN (In presence of alkaline)
dilute HCl
D NaCN (in aqueous ethanol)
dilute H2SO4
[TJC / MCQ / Q29]
Halogen Derivatives
20 In which compound is the carbon-halogen bond most easily hydrolysed by NaOH (aq)?
A chlorobenzene
B bromopropane
C fluoroethane
D 2,4,6 trichlorobenzene
[TPJC H1 / MCQ / Q17]
21 Which sequence shows the wrong order of increasing ease of hydrolysis?
A CH3CH2Br < CH3CH2I < C6H5CH2Cl
B
C6H5CH2Cl < C6H5CH2Br < CH3CH2I
C CH3CH2F < C6H5CH2Br < CH3CH2I
D
CH3CH2Cl < CH3CH2Br < CH3CH2I
[VJC H1 / MCQ / Q23]
22 A reaction sequence is given below. Which one of the following structures represents the
product Q?
CHBrCH3 KCN
P
ethanol
Br
A
dil HCl
reflux
Br
CHCH3
CHCH3
CO2H
CO2H
HO C
Cl
CHCH3
CHCH3
CH2NH2
COOH
Cl
[YJC / MCQ / Q24]
23 Dichlorodifluoromethane, CCl2F2, is a widely used aerosol propellants and as a refrigerant.

Which statement helps to explain why dichlorodifluoromethane is chemically inert?
A The carbon-fluorine bond energy is large.
B The carbon-fluorine bond has low polarity.
C Fluorine is highly electronegative
D Van der Waals forces between the molecules are weak
[YJC H1 / MCQ / Q19]
24 A bromoalkane, X, was heated under reflux with alcoholic potassium cyanide solution. The
organic product formed was then heated under reflux with dilute sulphuric acid. From this
mixture, 2-methylpropanoic acid was obtained. Which of the following compounds could be
X?
A 1-bromopropane
B 2-bromopropane
C 1-bromobutane
D 2-bromobutane
Halogen Derivatives
For each of the following questions, one or more of the three numbered statements 1 to 3 may
be correct. Decide whether each of the statements is or is not correct. The responses A to D
should be selected on the basis of:
A
B
C
D
1, 2 and 3
are correct
1
1 and 2 only 2 and 3 only

are correct
are correct
1 only is
correct
The formulae of two halogenoalkanes are given below.

C2H5Cl
C2H5Br
Which statements about the two compounds are correct?
X
Y
1 The induced dipole-induced dipole forces in X are stronger than those in Y.
2 The C-Cl bond is more polar than C-Br bond.
3 The C-Cl bond in X is harder to break than the C-Br bond in Y.
[TPJC / MCQ / Q38]
1 Dylan was asked by his chemistry tutor to differentiate
the three compounds below.
Dylan suggested the following method:
Step 1: To each of the 3 unknowns, add 1 cm3 of aqueous NaOH.
Step 2: Then add 1 cm3 of aqueous silver nitrate.
Step 3: Followed by aqueous hydrochloric acid, until blue litmus turns red.
Identify and explain the three errors in Dylan's method.
[HCI / II / Q4 a (modified)]
2 Compound A, 1-chlorobutane reacts with ethanolic sodium cyanide to yield product, B.
(a) With the aid of equations, name and describe the mechanism of the reaction and give the
structural formula of B.
(b) Explain how the rate of this reaction changes when 1-chlorobutane is replaced by 1bromobutane.
[MI / II / Q6 a, b ]
3
The hydrolysis of the halogenoalkanes shows a trend which can be related to their bonding.
The table below shows the observations after aqueous silver nitrate is added to each
halogenoalkane sample.
Compound
Observations
Precipitate
forms
almost immediately
CH3CHICH2CH3
CH3CHBrCH2CH3
Precipitate forms after 2 minutes
CH3CHClCH2CH3
Precipitate forms after 10 minutes
(i) By quoting suitable values from the Data Booklet, explain the above observations for the
hydrolysis of halogenoalkanes.
(ii) Predict, with a reason, whether a precipitate will be formed when aqueous silver nitrate is
added to CH3CHFCH2CH3.
[NYJC H1 / IIB / Q6 d ]
4
(a) When propane, CH3CH2CH3, reacts with chlorine, two different monochloropropanes are
produced.
(i) What condition is used for this reaction?
(ii) Draw the displayed formula of the two products
(iii) State the type of isomerism shown in the two products.
Halogen Derivatives
(iv) When the two products are refluxed with ethanolic potassium hydroxide, a compound B was
formed, which could rapidly decolourise bromine in CCl4. Give the displayed formula of B, and
write a balanced equation for the reaction between B and bromine in CCl4.
(b) Chlorofluorocarbons, CFCs, are small alkane molecules where a few of the hydrogen atoms
have been replaced by chlorine atoms and fluorine atoms. What are CFCs used for, what
environment hazard do they pose, and how, chemically, does this hazard arise.
[YJC H1 / IIB / Q6 d, e ]
5 Ethylbenzene can react with chlorine in two ways, depending on the conditions of the reaction.
CH2CH3
(i) State the condition needed for reaction I.
CH2CH3
CH2CH2Cl
(ii) Describe a test to distinguish between
Cl2
Cl2
A and B. State the reagents, conditions,
and the observations for each compound.
reaction II
reaction I
Write balanced equations for any reactions
CI
that occur.
B
[YJC H1 / IIB / Q7 c ] A
6 The graph below shows the reaction between aqueous sodium hydroxide and
a solution of a saturated alkyl chloride at temperature ToC.
[NaOH]/ mol dm-3
0.1
[RCl] = x mol dm-3

0.05
[RCl] = 2x mol dm-3

a
Time
(a) Referring to the graph above, deduce the order of reaction with respect to sodium
hydroxide and RCl and hence write down the rate law.
(b) Is RCl most likely to be a primary, secondary or tertiary alkyl halide?
(c) Draw a labelled energy profile diagram for the reaction.
(d) Briefly explain how one of the graphs above may be obtained experimentally.
(e) Aqueous hydrochloric acid and (CH 3)2CCHCl are separately reacted with aqueous
sodium hydroxide. How would the rates of reaction of these two compounds compare
with the rate of reaction of RCl in (b) above? Give your reasons.
Halogen Derivatives
Essay Questions
1 Suggest methods by which the following pairs of compounds could be distinguished from each
other by chemical tests. The distinguishing of some of these pairs may rely on a preliminary
breaking-up of the compounds and subsequent testing of the reaction products.
[AJC / III / Q5 c iii ]

2 Phenylethene, commonly known as styrene, is produced in industrial quantities from benzene
and ethylene via the intermediate ethylbenzene. It is used as a monomer to make plastics such
as polystyrene. Low levels of styrene occur naturally in plants as well as a variety of foods such
as fruits, vegetables, nuts, beverages, and meats. 1-bromo-1-phenylethane and 2bromoethylbenzene can be obtained from phenylethene and ethylbenzene respectively.
Describe a chemical test to distinguish 1-bromo-1-phenylethane from 2-bromoethylbenzene.
1-bromo-1-phenylethane
2-bromoethylbenzene
[HCI / III / Q2 c i ]
When a mixture of beryllium hydroxide pellets and ethanol is added to 2-chlorobutane, P, Q, R

and S are formed. Although P, Q and R do not react with PCl5, they decolourise potassium
manganate (VII), with only R giving an effervescence. S has the formula of C6H14O and is
found to rotate plane-polarised light.
(i) Suggest the identities of P, Q, R and S, explaining your reasoning.
(ii) Outline a mechanism for the formation of S from the reaction described above.
[NJC / III / Q5 d ]
4 The following concerns the reactions of some organic halogen derivatives.
(i) Describe the mechanism of the reaction between iodomethane and aqueous sodium
hydroxide.
(ii) Explain why the above reaction takes place very easily whereas conditions of 360 C and 150
atmospheres are required to convert chlorobenzene to phenol.
[NYJC / III / Q1 c i, iii ]
5
A halogenoalkane, Z, with a labelled carbon, C, undergoes the following reaction:
(i) State the reagents and conditions for the above reaction.
(ii) State the type of hybridisation and the shape with respect to the carbon atom, C , before and
after the reaction.
Halogen Derivatives
(iii) Describe a chemical test that would distinguish compound Z from chlorobenzene.
[TJC / III / Q1 e ]
6
The table below lists some information about five compounds, two of which are
chlorofluorocarbons (CFCs).
Name
Structure
Flammability
Lifetime / years
CFC-11
CCl3F
No
75
CFC-12
CCl2F2
No
108
HCFC-22
CHClF2
No
22
HCFC-123
CHCl2CF3
No
HFC-152
CH3CHF2
Yes
2
(i) Arrange the above hydrochlorofluorocarbons (HCFCs) and hydrofluorocarbons (HFCs)
compounds in order of increasing boiling points. Explain your answer in terms of structure and
bonding.
(ii) Give one use of CFCs in every day life.
(iii) Explain why the use of CFC poses a problem to the environment.
(iv) Hydrochlorofluorocarbons (HCFCs) and hydrofluorocarbons (HFCs) are possible replacements
for CFCs. Which compound in the above table is the best choice? Explain your answer.
[TJC / III / Q3 a ]
7
Explain why chloroethane undergoes nucleophilic substitution but not chlorobenzene.

[YJC / III / Q1 d ]
Hydroxy Compounds
4. Hydroxy
1 When an organic compound Q was treated with phosphorus pentachloride, fumes of hydrogen
chloride were evolved. When Q was warmed with alkaline aqueous iodine, a yellow precipitate
was formed. Which of the following was Q?
A CH3COOH
B CH3COCH2CH3
C (CH3)3COH
D CH3CH(OH)CH2CH3
[AJC / MCQ / Q24]
2 The anti-bacterial drug tetracycline has the formula
Which statement about tetracycline is correct?
A It does not react with SOCl2.
B It reacts with sodium carbonate to liberate carbon dioxide gas.
C 3 moles of HBr is formed when 1 mole of tetracycline reacts in
an excess of aqueous bromine in the dark.
D It reacts with sodium metal to liberate H2 gas.
[AJC / MCQ / Q25]
3 The structures below represent cyclohexane-1,2-diol.
Which of the following statements about the two isomers is incorrect?

A Both isomers can form dimers.
B Both isomers can rotate plane-polarised light.
C The cis isomer has a lower boiling point than the trans isomer.
D The cis isomer has a lower solubility in water than the trans isomer.
[MJC H2 2011 / Q16]
4 Phenol reacts with diazonium chloride as shown.
Which term describes this type of reaction?

nucleophilic substitution
electrophilic substitution
nucleophilic addition
electrophilic addition
[PJC H2 2011 / Q21]
Hydroxy Compounds
A compound has the following structure. All of the following

reagents will react with the above, except
A aqueous bromine
B phosphorous pentachloride
C neutral iron(III) chloride
D potassium cyanide
6 A yellow crystalline compound X gives compound Y

when treated with aqueous sodium carbonate. What
deduction can be made about the property of X?
A It is a stronger acid than phenol.
B It reacts with ethanoic acid.
C It can be oxidised to 2,4,6 trinitrobenzoic acid.
X
D It reacts with iodomethane to yield 2,4,6- trinitro-1-methoxybenzene.
[ACJC / MCQ / Q23]

OH
ONa
O2N NO2 O2N NO2
NO2 NO2
[ACJC / MCQ / Q27]

7 Organic compound A underwent the following reactions:
I reaction with phosphorus pentachloride
II boiling with potassium cyanide in alcohol
III boiling with aqueous sodium hydroxide
The final product was CH3CH2CH2COO-Na+. What was compound A most likely to have been?
A CH3CH2CH2=CH2
B CH3CH2=CH2
C CH3CH2CH2CH2OH D CH3CH2CH2OH
8 Which one of the following will be formed when CH 3CH(OH)CH2CH=CH2 is distilled with hot
acidified potassium dichromate(VI)?
A CH3COCH2CHO and CO2
B CH3COCH2COOH and CO2
C CH3COCH2CH(OH)CH2OHD
CH3COCH2CH=CH2
[HCI / MCQ / Q26]
9 Which of the following inorganic reagent may be used to distinguish between propan1ol and
propan2ol?
A sodium hydroxide
B lithium aluminium hydride
C concentrated sulphuric acid
D alkaline aqueous iodine
[HCI / MCQ / Q29]
Hydroxy Compounds
10 Which of the following reagents can be used to distinguish between 2-methylphenol &
phenylmethanol?
A KMnO4/ H+
B K2Cr2O7 / H+
C Br2 (g), U.V light
D Na (s)
[NJC / MCQ / Q25]
11 1 mol Compound Z gives the following observations when reacted with the specific reagents.
(i) Decolourises aqueous bromine,
(ii) Forms yellow precipitate with alkaline aqueous iodine,
(iii)Liberates one mole of hydrogen gas when two moles of sodium is added
What could Compound Z be?
A CH2=CHCH2CH(OH)CH3
[IJC / MCQ / Q16]

12 Which of the following is the correct synthesis route from 2-bromopropane to propene?
A
B
C
D
Step I
ethanolic NaOH, reflux
ethanolic NaOH, reflux
NaOH(aq), reflux
NaOH(aq), reflux
Step II
concentrated H2SO4, 170oC
NaOH(aq), reflux
ethanolic KOH, reflux
concentrated H2SO4, 170oC
[IJC H1 / MCQ / Q20]
13 In which sequence is it correctly stated that the value of pK a decreases continuously?

A C6H5OH
> CH3CHClCHClCH2OH > CH3CH2CH2CH2OH
> (CH3)3COH
B C6H5OH
> CH3CHClCHClCH2OH > (CH3)3COH
> CH3(CH2)3OH
C (CH3)3COH
> CH3CH2CH2CH2OH
> CH3CHClCHClCH2OH > C6H5OH
D CH3(CH2)3OH > (CH3)3COH
> CH3CHClCHClCH2OH > C6H5OH
[MI / MCQ / Q25]
14 Geraniol is found in rose oil and is used for the preparation of artificial scents. Upon controlled
oxidation, geraniol yields CH3COCH3, CH3COCH2CH2COOH and H2C2O4. A possible structure
of geraniol is
A CH3CH=C(CH3)CH2CH2C(CH3)=CHCH2OH
B CH3)2C=CHCH2CH2C(CH3)=CHCH2OH
C (CH3)2C=C(CH3)CH2C(CH3)=CHCH2OH
D (CH3)2C=CHCH2CH2C(CH2OH)=CHCH3
[MI / MCQ / Q26]
Hydroxy Compounds
15 2-methylpropan-1-ol can be converted into 2-methylpropan-2-ol as follows:
Which of the following sequences may be used for the conversion?

A Alcoholic KCN; Dilute H2SO4, reflux
B Concentrated H2SO4; cold alkaline KMnO4
C Al2O3 with heating; H2O with H3PO4 at high temperature and pressure
D Alcoholic NaOH; H2O with H3PO4 at high temperature and pressure
[MJC / MCQ / Q21]
16 The dehydration of propan-2-ol to form propene is thought to involve the following steps:
Which of the following statements is false?

A
Propan-2-ol acts as a base in Step 1.
B
H2SO4 is a catalyst in this reaction.
C
A possible side product of the reaction is CH3CH(OSO3H)CH3.
D
It is more likely for primary alcohols to proceed via this mechanism than tertiary alcohols.
[HCI H2 2011 / Q26]
17 Which one of the following alcohols will give the largest number of alkenes when treated with
concentrated sulphuric acid?
A
B
[MJC H1 / MCQ / Q21]

18 Which pair of the reactions could have the same common intermediate?
W CH3CH2CH3
intermediate
(CH3)2CHCN
X CH3CH(OH)CH3
intermediate
(CH3)2C(OH)CN
Y CH3CH=CH2
intermediate
CH3CH(OH)CH3
Z CH3CO2CH2CH2CH3 intermediate
CH3CH2CH2Br
A W and X
B W and Y
C X and Z
D Y and Z
[NJC / MCQ / Q27]
Hydroxy Compounds
19 Which one of the following formulae is the final product when CH 3CH(OH)CH2C(CH3)
(OH)CH2OH is heated under reflux with acidified aqueous potassium dichromate(VI)?
D
[NYJC / MCQ / Q24]
20 Compound Q was refluxed with aqueous sodium hydroxide and the resulting mixture was then
distilled. The distillate gave a positive tri-iodomethane test. The residue in the distillation flask,
after acidification, gave a white precipitate. Which of these could be Q?
A
CH3CH2COOCH2CH3
C
CH3CH2OCOC6H5
B
C6H5COOCH3
D
CH3CONHC6H5
[SRJC H2 2011 / Q26]
21 Which of the following alcohols produces only one alkene that displays cis-trans isomerism on
dehydration with hot concentrated sulphuric acid?
A pentan-1-ol
B pentan-2-ol
C pentan-3-ol
D butan-2-ol
[PJC / MCQ / Q28]
22 Experiments are carried out on three compounds P, Q and R. Equal volumes of 0.020 mol
samples of P, Q and R are separately reacted with an excess of zinc powder. The volumes of
hydrogen gas evolved at room temperature and pressure were recorded at 5 minutes interval.
The volumes of hydrogen gas evolved at the first 5 minutes were 100 cm3, 150 cm3 and 200
cm3. Which sequence of compounds matches these results?
100 cm3
150 cm3
200 cm3
A
P
Q
R
B
P
R
Q
C
Q
R
P
D
R
P
Q
[SRJC / MCQ / Q25]
23 The pinacol rearrangement involves the reaction of a diol in acidic conditions to form a
carbonyl compound as shown below.
Hydroxy Compounds
CH3
CH3
HO
CH3
O
H
OH
CH3
CH3
CH3
2, 3-dimethylbutane-2,3-diol
CH3
H2O
CH3
3, 3-dimethylbutan-2-one
Which of the following structural formulae is not a product of the pinacol

rearrangement of 2,3-diphenylpentane-2,3-diol with the structure as shown below?
CH2CH3
HO
OH
CH3
2,3-diphenylpentane-2,3-diol
A
B
O
O
C
CH2CH3
CH3
C
CH2CH3
CH3
D
O
O
C
CH2CH3
C
CH3
CH3
CH2
CH3
[PJC H2 2011 / Q25]
24 In a preparation of propene, propan-1-ol is added a drop at a time to a heated reagent P. The

impure propene is washed by being bubbled through a solution Q and then collected.
Which one of the following is a possible combination for reagents P and Q?
Hydroxy Compounds
A
B
C
D
P
acidified K2Cr2O7
zinc metal
concentrated H2SO4,
ethanolic NaOH
Q
dilute NaOH
dilute HCl
dilute NaOH
concentrated H2SO4
[TJC H1 / MCQ / Q21]
25 Compound E, C8H9ClO2, gives compound F, C8H7ClO2, on mild oxidation. F gives a yellow

precipitate on warming with alkaline iodine and reacts with 2 moles of aqueous bromine.
Which one of the following is the correct structure for E?
A
B
Cl
Cl
A
B
CH3CH(OH)
CC
OH
CH3CHCl
CH3CH(OH)
OH
D
OH
OH
Cl
CH2(OH)CH2
OH
TPJC / MCQ / Q26]

26 The compound ibuprofen is a powerful painkiller. What reacts completely with one
mole of ibuprofen?
A 2 mol of CH3COCl
B 2 mol of PCl5
C 3 mol of HCl
D 3 mol of NaOH
[TPJC / MCQ / Q27]
27 Which reagent could detect the presence of added alcohol in petrol consisting mainly of a
mixture of alkanes and alkenes?
A Na
B 2,4-dinitrophenylhydrazine
C Br2(l)
D KMnO4 (aq)
28 Which one of the following compounds is not a product of the vigorous oxidation of
geraniol?
Hydroxy Compounds
[VJC / MCQ / Q22]
29 The compound
reacts with
A hot HCl(aq) to form
NaOH(aq) to form
C HCl in CCl4 to form
hot acidic KMnO4 to form
[VJC / MCQ / Q24]

30 What are the products formed when compound G is treated with an excess of hot acidic
KMnO4?
CH2=C(CH3)CH=CHCH2CH2OH
Compound G
A
D
31 Which one of the following will be formed when pentan-1,4-diol is distilled with hot acidified
potassium dichromate(VI)?
Hydroxy Compounds
A CH3COCH2CH2CHO
CH3COCH2CH2COOH
C CO2 and HOOCCH2CH2COOH
CH3CH(OH)CH2CH2CHO
32 Which of the following compounds:

(i)
is unaffected by hot alkaline potassium manganate(VII) and
(ii)
gives hydrogen when treated with sodium?
A (CH3)2CHCOCH3
B (CH3)3COH
C (CH3)2CHCH2OH
D CH3CH2CH(OH)CH3
[YJC / MCQ / Q30]
For each of the following questions, one or more of the three numbered statements 1 to 3 may be
correct. Decide whether each of the statements is or is not correct. The responses A to D should
be selected on the basis of:
A
B
C
D
1, 2 and 3
are correct
1

are correct
are correct
1 only is
correct
Which of the following reagents can be used to distinguish between the following two
compounds?
1 Br2 (aq)
Na
[AJC / MCQ / Q38]
2 The relative molecular mass of the organic compound increases when ethanol reacts with
1 acidified potassium chromate(VI) solution followed by distillation.
2 acidified potassium manganate(VII) solution.
3 sodium bromide and concentrated sulphuric acid.
3
KMnO4
Chloroethane can be prepared from bromoethane as follows:

step G
C2H5Br
step H
C2H5OH
C2H5Cl
What deductions can be made about the above reaction sequence?

1 Step G involves nucleophilic substitution.
1 Hot aqueous sodium hydroxide is the reagent in step G.
3 Step H can take place at room temperature.
[MI / MCQ / Q39]
4
Which of the following is TRUE?

1 More branching of molecules results in an increase in boiling point.
2 As the number of carbon atoms increases, solubility of alcohols in water decreases.
3 Methylbenzene has a higher melting point than benzene.
[MI H1 / MCQ / Q26]
Hydroxy Compounds
Monomer A reacts with diphenol B to give a polymer as shown in the reaction scheme below.
Which statement(s) is/are correct?

1 In the reaction, nucleophilic substitution takes place.
2 One mole of HCl is removed for each unit of the polymer formed.
3 Both monomer B and the polymer formed give a purple complex with neutral iron (III)
chloride solution.
[MJC / MCQ / Q40]
6
Which of the following pairs of compounds give the same organic products when subjected to
a hot solution of acidified potassium manganate (VII)?
3 CH3CH2CH2OH and CH3CH(OH)CH3

Which of the following compounds forms a yellow precipitate when warmed with alkaline
aqueous iodine?
1 Butan-2-ol
2 1-phenylethan-1-ol
3 2-phenylethanol
Hydroxy Compounds
[NYJC / MCQ / Q38]

8
Binapacryl is used as a fungicide. From an examination of its structure,

it can be deduced that
1 its aqueous solution will be acidic.
2 it cannot exist in optically active forms.
3 it will react with ethanol in the presence of concentrated sulphuric acid to
give an ester.
[TJC / MCQ / Q39]
1 Alcohols often have an odor described as 'biting' that 'hangs' in the nasal passages. Alchohol in
the form of beverages has been consumed by humans since pre-historic times, for a variety of
hygienic, dietary, medicinal, religious, and recreational reasons. While infrequent consumption
of alchohol (especially ethanol) in small quantities may be harmless or even beneficial, larger
doses result in drunkenness or intoxication (which may lead to a hangover as the effect wears
off) and, depending on the dose and regularity of use, can cause acute respiratory failure or
death and with chronic use has medical repercussions. Because alcohol impairs judgment, it
can often be a catalyst for reckless or irresponsible behavior. Below show the formulae of two
different alcohols, A and B.
CH3CH(OH)CH2CH3
(CH3)3COH
A
B
Describe one chemical test by which A could be distinguished from B. You should state the
reagents and conditions you would use and the observations you would make with each
compound undergoing the test.
[IJC H1 / IIA / Q1 ]
2 Spices are often responsible for the flavour in many foods. Two types of compounds present in
one of the spices are shown below :
What would be observed when the following reactions are carried out?
In each case, give the name or formula of the reaction product which is responsible for the
observation you have made.
(i)
Substance E with PCl5.
(ii)
Substance E with sodium metal.
(iii)
Substance F with hot acidified potassium manganate (VII).
(iv)
Suggest how E could be converted into F in the laboratory.
[IJC H1 / IIB / Q1 c ]
3
There are two different alcohols that have the molecular formula C 3H8O.
Hydroxy Compounds
Draw the displayed formula of the 2 isomers and suggest a chemical test that can be used to
distinguish them. Include any observations that would be seen.
[SRJC H1 / IIB / Q1 f ]
4
Menthol, C10H20O, can be synthetically made from peppermint

and is used in skin lotions to reduce itching. The structural formula
of menthol is shown:
(a) Label all the chiral carbons (with *) in the structure shown
above.
(b) Menthol can be used in the following reaction scheme:
(i) Suggest reagents and conditions for Steps 1 and 2.

(ii) Suggest the structural formula of the intermediate compound X.
(c) Compound Y, a structural isomer of menthol, gives a yellow precipitate on warming with
alkaline aqueous iodine. Suggest a structural formula of the isomer Y.
[TPJC / II / Q7 ]
[TPJC H1 / IIA / Q5 ]
5
Suggest how the three alcohols (namely butan-1-ol; butan-2-ol and 2-methylpropan-2-ol) could
be distinguished from each other experimentally. Include observations where appropriate.
[TPJC H1 / IIB / Q10 c ]
Use the information below to identify the compounds A to E. Explain your reasoning.
Compounds A and B each has a relative molecular mass of 60 and an empirical formula of
C3H8O. During the reaction with acidified potassium dichromate (VI) solution, A forms only one
organic product, C. Under similar conditions, B produces compound D which can be further
oxidised to E.
[VJC H1 / IIB / Q7 a i ]
Essay Questions
Hydroxy Compounds
1 Suggest methods by which the following pairs of compounds could be distinguished from each
other by chemical tests. The distinguishing of some of these pairs may rely on a preliminary
breaking-up of the compounds and subsequent testing of the reaction products.
(i)
(ii)
[AJC / III / Q5 c i, ii ]
2 Describe a simple chemical test that you could use to distinguish the following compounds. You
are to include reagents and conditions, observations and a balanced equation(s) in each case.
OH
(i)
H
C
and
(ii)
and
C
O
CH3
CH2OH
[ACJC / III / Q1 d ]
3 Concentrated sulfuric acid reacts with many organic compounds, forming water as one of the
products. Three examples are shown below.
Concentrated sulfuric acid dehydrates methanoic acid to form a gas, A, with the same
molar mass as ethene.
Concentrated sulfuric acid dehydrates sucrose, C12H22O11, to form a black solid, B.
Concentrated sulfuric acid dehydrates ethane-1,2-diol to form a compound C with a molar
mass of 88 g mol1. In this reaction, 2 moles of ethane-1,2-diol produce 1 mole of C and 2
moles of H2O.
Suggest the identities of A, B and C. Write equations for each reaction and deduce the
structural formula of C.
[HCI / III / Q1f ]
For each of the following pairs of compounds, suggest methods of not more than two steps, by
which they can be distinguished from each other. State the reagents and conditions clearly and
describe what you would see.
Hydroxy Compounds
(i)
and
(ii)
[IJC / III / Q3 e ]
and
5(i)Compound D can undergo the following reaction.
Given that the product E is not chiral, suggest a possible structure of E. And hence, deduce the
structure of C8H12O4.
(ii) F is another possible product from step I. However, F contains a chiral centre and it forms a
polymer in step II.
Suggest a possible structure of F and explain why F does not form the same type of product as
E in step II when it is treated with concentrated sulphuric acid.
[NJC / III / Q2 a ii, iii ]
6
Suggest one simple chemical test which would enable you to distinguish the following pairs of
compounds. State reagent(s) and condition(s) and their corresponding observations.
CH3
H3C-HC=CH-CH2-C H3
(CH3)2C=CH-C-CH3
OH
OH
compound C
compound D
[TPJC / III / Q3 a ii ]
The benzaldehyde can be reduced to phenylmethanol, C 6H5CH2OH, which has a different

acidity from that of phenol, C 6H5OH. Explain the difference in acidity between phenylmethanol
and phenol.
[VJC / II / Q4 c ]
8 Joseph Priestly prepared hydrogen chloride in 1772 and found that the compound was a
colourless gas at room temperature. It formed white fumes of hydrochloric acid upon contact
with atmospheric humidity. Hydrogen chloride gas as well as hydrochloric acid are important in
technology and industry.
Hydroxy Compounds
Examples of applications include hydrochlorination of rubber, treatment of cotton

wool, semiconductor industry, etc. Draw the structural formulae of the organic
products formed when the compound (shown on the right) reacts with:
A: HCl(g), ZnCl2
B: CH3COOH, hot concentrated H2SO4
[YJC / III / Q2 d i ]
9
When phenol is added to aqueous sodium hydrogencarbonate, there is no evolution of gas, but
a colourless gas is evolved when 2,4,6-trinitrophenol is used instead. Explain the above
observation as fully as possible, writing a balanced equation for the reaction that occurred.
[YJC / III / Q4 c ii ]
5. Carbonyl
Carbonyl Compounds
1 Oxidation of an alkene Y gives a diol; further oxidation gives a diketone. Which one of the
following could be Y?
A CH3CH=CH2
B CH3CH=CHCH3
C CH3CH=C(CH3)2
D (CH3)2C=C(CH3)2
[AJC / MCQ / Q21]
2 Oestrone, a sex hormone, has the following structural formula.
Which reagent would be expected to react with this compound?

A lithium aluminium hydride
B concentrated sulphuric acid
C alkaline aqueous iodine
D acidified potassium manganate(VII)
[AJC / MCQ / Q27]
3 Which one of the following represents the final product obtained when the
alkene below is reacted with cold, alkaline manganate(Vll) ions followed by hot
acidified potassium dichromate(Vl) solution?
A
4 Citronellol is a colourless oily liquid having a rose-like odour. It is the active ingredient in over
30 essential oils and is a major component in perfumes, cosmetics and soaps. It may be
prepared synthetically from compound W using reagent X.
Carbonyl Compounds
Which of the following could W and X most likely be?

5 Ethanal can react with ammonia as shown.
CH3CHO + NH3 CH3CH(OH)NH2
What type of reaction is this?
A additionelimination
B electrophilic addition
C freeradical addition
D nucleophilic addition
[AJC H2 2011 / Q25]
Methyl isocyanate, CH3-N=C=O, readily reacts with nucleophiles. By analogy with the
chemistry of other carbonyl compounds, predict which atom will be attacked by a nucleophile.
A carbon atom of the isocyanate group
B carbon atom of the methyl group
C nitrogen atom
D oxygen atom
[SRJC / MCQ / Q27]
Carbonyl Compounds
7 The mechanism below shows how butanone reacts with hydrogen cyanide.
Which of the following statements is true?

A The product mixture is optically active.
B The rate of reaction of hydrogen cyanide with butanal is faster than that with butanone.
C Cyanohydrin produced can react with ammonia at high pressure to form amine.
D Cyanohydrin produced requires potassium manganate(VII) to form carboxylic acid.
[ACJC H2 2011 / Q24]
8 Ethanal reacts with CN from HCN in the presence

of a weak base as shown.
In a similar reaction, CH2COCH3 ions are generated
when CH3COCH3 reacts with a strong base. Which
one of following compounds is the product when ethanal reacts with CH2COCH3?
A CH3CH(OH)CH2COCH3
B (CH3)2C(OH)CH2CHO
C (CH3)2C(CHO)CH2OH
D (CH3)2C(OH)COCH3
[NJC / MCQ / Q28]
Carbonyl Compounds
Pentan-2-one is treated with cold hydrogen cyanide in the presence of traces of sodium
cyanide. The product X of this reaction is then boiled with hydrochloric acid to give Y. What
are X and Y likely to be?
A
H OH H
H3C C C C CH3
H CN H
H H H OH
H3 C C C C C H
H H H CN
H OH
H CN
H H
H3 C C C
H H
H3C C C
CH3
H COOH H
H H H OH
H 3C C C C C H
H H H COOH
H OH
H3C C C CH3
D
H OH
H3C C C CH3
H COOH
OH
C CH3
CN
H H
H3 C C C
H H
OH
C CH3
COOH
[SRJC / MCQ / Q28]
10 Which of the following reagents will give similar results for both butanal and butanone?
A Aqueous alkaline iodine
B Fehlings solution
C Acidified aqueous potassium dichromate(VI) D 2,4-dinitrophenylhydrazine
11 Compound B will show a positive test with all of the
following reagents except
A PBr3, reflux
B 2,4-dinitrophenylhydrazine, warm
C Acidified KMnO4, reflux
D Na, room temperature
12 The first stage in the synthesis of antipyrine, a drug used in reducing fever, is the
Carbonyl Compounds
reaction between compound T and phenylhydrazine.

CH3COCH2CO2CH2CH3 +
NHNH2
What will be the product S?

A
NHCOCH2COCH3
NHCH2CO2CH2CH3
C
D
CH3COCH2CO
NH N
NHNH2
C
CH2CO2CH2CH3
CH3
[DHS H2 2011 / Q24]

13 Compound A has the following formula.
Which one of the following statements is incorrect about Compound A?
A A white precipitate is formed when aqueous silver nitrate is added.
B An orange precipitate is formed with 2,4-dinitrophenylhydrazine.
C A pale yellow precipitate is formed when warmed with alkaline
aqueous iodine.
D An acidified solution of KMnO 4 decolourised on heating.
14 Which of the following reagents will cause a colour change when the reagent is added to
compound P?
A warm, alkaline aqueous iodine
B 2,4-dinitrophenylhydrazine
C hot, acidified KMnO4
D Fehlings reagent
NYJC H1 / MCQ / Q21]
15 Limonene, A, occurs in oil of lemons and is used to flavour some citrus drinks.
Which of the following is true about limonene?
A It exhibits geometric isomerism.
B Upon reaction with hot acidified potassium manganate (VII), the product
forms an orange precipitate with 2,4-dinitrophenylhydrazine.
C It reacts with bromine dissolved in an inert solvent to form a compound
with the molecular formula C10H16Br2.
D It reacts completely with 1 mole of hydrogen in the presence of a nickel
catalyst to yield a saturated compound.
16 Which reagent gives the same visible result with propanal and with propan-2-ol?
Carbonyl Compounds
A Fehlings reagent
C acidified potassium manganate (VII)
B concentrated sulphuric acid

D 2,4-dinitrophenylhydrazine
17 Oestrone is a female sex hormone.

How does the compound above reacts with 2,4dinitrophenylhydrazine reagent (2,4-DNPH), Tollens reagent and
Fehlings reagent?
A
B
C
D
2,4-DNPH
Tollens'
Fehling's
negative
positive
positive
positive
negative
negative
positive
positive
negative
negative
negative
positive
18 Compound Q was subjected to the following tests and the results are recorded below. Which of
the following could be compound Q?
Reagent and conditions
observations
Acidified KMnO4, warm
Solution turns from purple to colourless. CO2 is
evolved.
Fehlings reagent, warm
No precipitate seen.
Tollens reagent, warm
Silver mirror observed.
A
[HCI / MCQ / Q22]

19 The compound C3H7Br undergoes a sequence of reactions as follows:
OH (aq)
Acidified
K2Cr2O7
Tollens
reagent
C3H7Br
X
Y
Z + silver mirror
What could be the formulae for X, Y and Z?
X
Y
Z
A CH3CH2CH2OH
CH3CH2CO2H
CH3CH2CHO
B CH3CH2CH2OH
CH3CH(OH)CH2OH
CH3CO2H
C CH3CH2CH2OH
CH3CH2CHO
CH3CH2CO2H
D CH3CH(OH)CH3
CH3COCH3
CH3CO2H
[MI H1 / MCQ / Q15]
Carbonyl Compounds
20 How many structural isomers with the molecular formula C 4H8O can reduce Tollens reagent
to form a silver mirror?
A 1
B 2
C 3
D 4
21 An organic compound G is refluxed with acidified potassium manganate (VII) to produce 2
organic compounds H, I and an odourless gas. H gave negative results with Fehlings reagent
but gave a pale yellow precipitate with iodine in an alkaline solution. Effervescence was
observed when I was treated with aqueous sodium carbonate. Both H and I were found to yield
orange crystals when treated with 2,4-dinitrophenylhydrazine.
What is the structure of G?
A
D
22 The table shows the observations of the chemical tests conducted on compound U.
Chemical test
Observations
Warm with 2,4-dinitrophenylhydrazine Orange precipitate
Warm with Tollens reagent
Silver mirror
Warm with alkaline aqueous iodine
Yellow precipitate
From the observations of the chemical tests, what could U be?
A CH3CHO
B CH3COCH3
C CH3CH2CHO
D CH3CH(OH)CH3
23 An organic compound has the following properties.

It gives a yellow precipitate with aqueous alkaline iodine. When warmed with acidified
potassium dichromate(VI), the solution remains orange.
Which one of the following is the organic compound?
D
[NJC / MCQ / Q21]
Carbonyl Compounds
24 When an alcohol, H, is treated with hot acidified aqueous potassium manganate(VII), the final
oxidation product gives a positive tri-iodomethane test. Which of the following compounds
could correspond to H?
A C6H5CH2OH
B C2H5OH
C CH3CH(OH)C2H5
D C6H5CH(OH)C2H5
[TJC / MCQ / Q21]
25 How many structural isomers with the molecular formula C 4H8O2 (exclude ether) give an
orange precipitate with 2,4-dinitrophenylhydrazine but no precipitate with alkaline aqueous
iodine?
A 3
B 4
C 5
D 6
[VJC / MCQ / Q28]
26 Aldehydes can undergo addition reactions with a variety of compounds of the form HX
according to the following equation.
C
HX
OH
c a t a ly s t
C
H
An example of such a reaction is the formation of cyanohydrin, where X = CN.

Which of the following compounds cannot be obtained by such an addition reaction to
aldehyde, followed by dehydration?
A
D
[YJC H2 2011 / Q25]
Carbonyl Compounds
27 The Wittig reaction involves the reaction of a carbonyl compound with a phosphorus ylide to
give an alkene. The reaction occurs because of an important oxaphosphetane intermediate.
Which one of the following structures shows the product of the reaction between the following
compound and the phosphorus ylide shown?
[RI H2 2011 / Q27, 28]

28 Butanone, CH3CH2COCH3 , may be used as the starting point for synthesizing Compound Z,
CH3CH = C(COOH)CH3 . Which is best process for producing compound Z?
A CH3CH2COCH3 CH3CH2C(OH)2CH3 CH3CH2C(OH)(CN)CH3 Z
B CH3CH2COCH3 CH3CH2C(OH)(CN)CH3 CH3 CH = C(CN)CH3 Z
C CH3CH2COCH3 CH3CH2CH(OH)CH3 CH3 CH = C(CN)CH3 Z
D CH3CH2COCH3 CH3 CH = C (OH)CH3 CH3 CH = C(CN)CH3 Z
[TPJC / MCQ / Q22]
Carbonyl Compounds
A
B
C
D
1, 2 and 3
are correct

are correct
are correct
1 only is
correct
1 A synthesis pathway, with W and X as the intermediates, is shown below:
Which of the following statements are true about the synthesis?

1 Step I is a nucleophilic addition reaction.
2 Step II is an electrophilic substitution reaction..
3 Step III is a reduction reaction.
[VJC / MCQ / Q40]
2 Which of the following statements are true for compound A?
1 It gives a orange precipitate with 2,4-dinitrophenylhydrazine.

2 It gives a silver precipitate with Tollens reagent.
3 It undergoes esterification with phenol.
[AJC / MCQ / Q39]
3 The compound X, CH3COCH2CHO, was reacted in separate experiments with:
(i) 2,4-dinitrophenylhydrazine (ii) alkaline aqueous iodine
(iii) Tollen's reagent [Ag(NH3)2]+(aq)
Which statements about these reactions are correct? One mole of X could
1 react with two moles of 2,4-dinitrophenylhydrazine in (i).
2 form one mole of CHI3 in (ii).
3 form one mole of CH3COCH2COOH in (iii).
[ACJC / MCQ / Q40]
4
Safranal is a component of the yellow dyestuff saffron.

Which one of the following descriptions about safranal is/are correct?
1 It gives an orange precipitate with 2,4-dinitrophenylhydrazine.
2 It does not react with Fehlings solution.
3 All atoms in the molecule lie in one plane.
[NYJC / MCQ / Q39]
Carbonyl Compounds
5 The following compound Y is a flavouring agent in food.

Which of the following statement is not true?
1 Compound Y will give brick red precipitate with Fehlings solution.
2 Compound Y will give yellow precipitate with aqueous alkaline
iodine.
3 Compound Y will decolourise an acidified solution of potassium
manganate(VII)..
[PJC H1 / MCQ / Q30]
6
Which of the following tests can be used to distinguish between the two organic compounds
below?
1 Na metal
2 aqueous bromine
3 acidified KMnO4
7
Two female sex hormones are oestrone and oestradiol.

CH3
HO
CH3
OH
HO
oestrone
oestradiol
Which of the following reagents could not be used to distinguish between the two hormones?
1 Fehlings solution
2 I2 in NaOH (aq)
3 Sodium metal
Carbonyl Compounds
1 Another commonly used oxidising agent for organic reactions is potassium manganate(VII),
KMnO4.
(i) Draw the full structural formula of the organic product that is formed when acidified potassium
manganate(VII) is added separately to compounds A and B.
(ii) Describe a reaction by which you could distinguish between A and B. State the reagents,
conditions and the observations you can make with each compound.
(iii) Compound B reacts with hydrogen cyanide. State the type of reaction and the conditions
necessary for this reaction to take place?
(iv) Draw the structure of the organic product that is formed.
[AJC H1 / IIB / Q5 c, d ]
2 Compound B is a ketone which has the formula C4H8O.
(i) It gives a positive triiodomethane test. Draw the structure of the group present in B.
(ii) Give the structure of the product C obtained in the triiodomethane test.
I2 + NaOH(aq)
B
CHI3 + C
(iii) Deduce the structure of B using the available information from (i) and (ii).
(iv) Describe the use of 2,4-dinitrophenylhydrazine with B.
(v) Compound B can undergo further reaction as shown in the scheme.
B
H2
SOCl2, reflux
Give the structural formula for D and E.

[ACJC H1 / IIB / Q1B a, b, c ]
3
Compound X
Compound Y
State how compound Y can be synthesized from Compound X.
Your answer should include the intermediate compound(s) formed in each step and the
reagents and conditions required in each step(s).
[MI H1 / IIB / Q1 b ]
Carbonyl Compounds
4 Cinnamaldehyde, acetylhydroquinone and vanillin are three common carbonyl compound

derivatives used in industry.
(a) Using cinnamaldehyde as the starting material, state suitable reagents and conditions to carry
out the following type of reaction.
(i) addition reaction of the aldehyde group
(ii) oxidation of only the alkene group
(iii) oxidation of only the aldehyde group
For each reaction, draw the structural formula of the organic product.
(b)
(i) Both acetylhydroquinone and vanillin react with 2,4-dinitrophenylhydrazine. Give the
observation expected and write a balanced equation for the reaction of acetylhydroquinone
with 2,4-dinitrophenylhydrazine.
(ii) Describe a simple chemical test each to distinguish acetylhydroquinone from vanillin. State the
reagent and condition, and describe what would be seen with each compound.
[MJC H1 / IIB / Q6 a, b ]
5 Cyclohexanone can be converted to cyclohexanamine, in 3 steps as shown below. Give the
reagents and conditions for steps 1 to 3 and draw the structures for A and B in the boxes
provided.
O
A
Step 1
NH2
Step 3
Step 2
[NYJC / II / Q6 ]
6
Use the information below to identify the compounds F to G. Explain your reasoning.
F and G each has the molecular formula C 4H8O. Both produce an orange precipitate with
2,4-dinitrophenylhydrazine but only F reacts with an alkaline solution of iodine.
[VJC H1 / IIB / Q7 a ii ]
Carbonyl Compounds
The following data is related to an organic substance Z.

Physical state at r.t.p.
Liquid
Molecular formula
C4H6O
Chemical test
Reagent
Results
2,4-dinitrophenylhydrazine
Orange precipitate
Tollens reagent
No reaction
Bromine water
Decolourised
(a) What are the conclusions that can be made about the structure of Z by considering:
(i) test A alone
(ii) test A and B together
(iii) test C alone
(b) Suggest a possible structure of Z.
[YJC H1 / IIA / Q2 a, b]
8
Ibuprofen was discovered by Boots Pharmaceuticals in the late 1960s and was used to treat
arthritis and similar problems. It has now become the third largest selling analgesic after
paracetamol and aspirin. The first step in the manufacturing process is the conversion of 2methyl-1-phenyl-propane, known as IBB (this is short for its common name, isobutylbenzene),
into the compound known as IBAP, shown in the following reaction sequence:
H
CH3
CH3
CH3
+ H3C
CH3
Cl
AlCl3
O
IBB
CH3
IBAP
In the second stage of the industrial synthesis of ibuprofen, IBAP is converted into the
intermediate compound A, whose structural formula is shown below. This then undergoes
H CH3
several further H
reactions
to produce ibuprofen.
CH3
H
CH3
Several steps
H3 C
Compound A
CH3
O
H3 C
OH
Ibuprofen
(a) State the functional group present in IBB:

(b) What is the type of reaction that IBB has undergone?
(c) Describe a simple chemical test to distinguish between IBB and IBAP, giving the reagents and
conditions, observations, and balanced equations for the positive test.
Carbonyl Compounds
(d) Name the functional group which is present in compound A, but not in IBB or IBAP.
(e) Suggest reagents and conditions that can be used to convert compound A to Ibuprofen in one
step in the laboratory?
(f) Suggest a reason why this method is not used in the actual industrial process to synthesize
Ibuprofen.
(g) Complete the reaction scheme below with compound A as the starting material. Draw the
structural formula of the organic products formed, or give a suitable reagent and conditions (if
any), in each of the boxes provided.
CH3
(i)
CH3
HCN, NaOH(aq); 10
C 20 C
O
H3C
Compound A
Tollens
reagent,
heat
(ii)
(iii)
CH3
CH3
Br
H3C
CH3
Br
O
C
H
CH3
O
H
H3C
or
[YJC H1 / IIA / Q5 ]
Carbonyl Compounds
Essay Questions
1
propanone
ethanoic acid
Mr
58.0
60.0
density/g cm3
0.79
1.05
solubility in water
miscible
fully miscible
(a) Explain the differences in density and solubility in water for propanone and ethanoic acid.
(b) Give a detailed description of the mechanism reaction between propanone and hydrogen
cyanide.
[ACJC / III / Q4 b, c ]
2 Compound P can be synthesised from cinnamaldehyde.
Compound P
cinnamaldehyde
(i) Suggest a synthetic pathway for the formation of Compound P from cinnamaldehyde. Suggest
appropriate reagents and conditions as well as structures of any intermediates formed.
(ii) Give the structural formula of the organic products formed when Compound P is refluxed with
acidified potassium manganite .
(iii) Compound P is able to rotate the plane of polarised light due to the presence of the chiral
carbon atom. Explain why Compound P synthesised from cinnamaldehyde in part (i) does not
exhibit this
behaviour.
[IJC / III / Q2 a ii, iii, iv ]
3 Vanillin and acetylhydroquinone are two
commonly used carbonyl
compound derivatives used in industry. The largest single use of vanillin
is as a flavoring, usually in sweet foods such as ice cream and
chocolate while acetylhydroquinone is used in developing photographic
emulsions. Both compounds exists as yellow solids that are soluble in
water to form a yellow solution which is perceptible even at minute
concentrations.
(a) Both organic compounds react with hydrocyanic acid, HCN at different rates. This reaction
requires an amount of a base such as sodium hydroxide to be added.
(i) Name and describe the mechanism between HCN and acetylhydroquinone. Explain clearly the
role of the base in this reaction.
(ii) In the reaction of vanillin with HCN, only a small amount of a base is required. Suggest why for
acetylhydroquinone, more sodium hydroxide is required for any significant reaction to occur.
(b)
(i) Both vanillin and acetylhydroquinone reacts with 2,4-dinitrophenylhydrazine. Give the
observation expected and write an equation for the reaction with acetylhydroquinone.
Carbonyl Compounds
(ii) Give one positive chemical test each, for vanillin and acetylhydroquinone, which will allow the
two compounds to be distinguished from one another. State the reagents, conditions and
observations expected.
[MJC / III / Q2 a, b ]
4 Three unlabeled reagent bottles are known to be containing three compounds below.
X
Y
Z
O
C
CH2
CH2OH
CH3
CH
OH
OH
O
CH2
(i) Suggest how the identity of the compound in each bottle can be identified by simple chemical
tests. Your answer should state clearly the reagents and conditions used for the test and the
observations of the reactions that allow you to reach your conclusion
(ii)
What type of reaction is undergone when compound X reacts with hydrogen cyanide
and trace amount of NaOH? State the conditions necessary for the reaction to take place.
(iii)
Briefly describe the steps in the mechanism of this reaction.
[NYJC / III / Q4 d ]
5
Chloral hydrate is an unstable drug that can decompose easily to form chloral
with a loss of water molecule. Chloral reacts with cold alkaline hydrogen
cyanide under appropriate conditions to yield compound B.
Chloral hydrate
(i) Draw the displayed formula for compound B.
(ii) Outline the mechanism for the reaction of chloral with hydrogen cyanide.
[TPJC / III / Q4 a ii ]
6
Propose a reaction synthesis route for the following conversion:

CH3 H
O
CH3 H H
H3C C C C
CH3
H3C C C C CH2
OH H
(State reagents and conditions, and show all intermediates)
[YJC / III / Q4 a ]
Squaric acid is an unusual organic compound with molecular formula, C 4H2O4, and its systematic name
is 1,2dihydroxycyclobutene-3,4-dione. Suggest what you would expect to see when squaric acid
reacts with :
(a) 2,4-dinitrophenylhydrazine agent
(b) phosphorus pentachloride.
Give equations for the reactions that occurred.
[YJC / III / Q5 a i, c]
Carboxylic Acids
6. Carboxylic Acids and

1 Which of the following pair of compounds would produce the same carboxylic acid upon
hydrolysis?
A
B
C
D
CH3CH2COCl
CH3CH2CN
CH3CH2CN
C6H5CONH2
CH3CO2CH3
CH3CO2CH2CH3
CH3CH2CO2CH3
C6H5NHCOCH3
[AJC / MCQ / Q26]
2 Butanoic acid can be obtained from the following reactions except

A refluxing CH3CH2CH2CH2OH with K2Cr2O7/ H+
B refluxing CH3CH2CH2CH2CN with dilute H2SO4
C refluxing CH3CH2CH2CHO with [Ag(NH3)2]+,followed by acidification
D refluxing CH3CH2CH2COOCH3 with dilute H2SO4
3
The diagram below shows the synthesis of Compound S starting from benzene.
Which one of the following gives the correct types of reactions for step 1 to 3?
A
B
C
D
4
Compound V is formed from ethanal via a series of reactions below.

Which of the following reactions is not represented in the sequence?
A nucleophilic addition
B electrophilic addition
C hydrolysis
D condensation
[HCI / MCQ / Q24]
5 Which of the following compounds reacts with PCl5 at room temperature to produce an
organic compound that reacts vigorously with water?
A
CH3COOH
B CH3COOCH3
CH3CH2CH2OH
D HOCH2CH2OH
[ACJC / MCQ / Q29]
Carboxylic Acids
6 The structure of an organic compound V is as shown:

Which one of the following statements is true?
A The six-membered carbon ring in V is planar.
B V reacts readily with cold HCN under acidic conditions.
C V changes warm acidified aqueous potassium dichromate from orange to green.
D Reaction of sodium carbonate with V produces a gas which forms a white precipitate with
calcium hydroxide.
7 A mixture is made by mixing excess aqueous sodium carbonate with phenylmethanol,
phenol and methanoic acid. Which organic species is/are present in the organic layer of the
solution?
A phenylmethanol
B methanoic acid
C phenylmethanol and phenol
D phenylmethanol, phenol and methanoic acid
[IJC / MCQ / Q26]
8 The following compound, Vitamin C is soluble in water.
Which one of the following statements is correct?
A The molecule is planar.
B It can exist as cis-trans isomers.
C It can react with hot sodium hydroxide.
D It can react with 2,4-dinitrophenylhydrazine to form a bright orange precipitate.
[MI H1 / MCQ / Q20]
9
Which one of the following compounds is not reduced by LiAlH4?

A C6H5COOH
B CH3COCH3
C CH2=CH2
D CH3CHO
10 How many moles of H2 react with one mole of the following compound?
A 2
B 3
C 4
D 5
[NJC / MCQ / Q23]
11 Citric acid, which causes the sharp taste of lemon juice, has the following
formula. Which of the following reacts completely with 1 mole of citric acid?
A 3 moles of PCl5
B 3 moles of NaHCO3
C 4 moles of HCl
D 4 moles of NaOH
[PJC H1 / MCQ / Q24]
12 When an organic compound X was treated with phosphorous pentachloride, fumes of HCl
were evolved. When X was warmed with acidified concentrated potassium manganate (VII),
the solution turned colourless from purple.
A CH3CH2CHO
B CH3COCH3
C (CH3)3COH
D C6H5CH=CHCO2H
13 A compound P reacts with PCl5 to form hydrogen chloride gas and decolourises hot
acidified potassium manganate(VII). Which of the following could P be?
Carboxylic Acids
HO
C
H3C C
C C
H3C C
OH
CH3
O
CH3
H3C C CH3
OH
[YJC / MCQ / Q27]
14 Which one of the following pairs of substances react together to form an organic product that
gives a neutral solution?
A C6H5OH and Na
B C6H5NH2 and HCl
C C6H5CH2CH(NH2)COOH and HCl
D C6H5COCH3 and LiAlH4
[VJC / MCQ / Q26]
15 Which one of the following gives the correct order of acid strength (strongest first) for
propanoic acid, 2-chloropropanoic acid, and 3-chloropropanoic acid?
strongest
CH2ClCH2CO2H
CH3CHClCO2H
CH3CHClCO2H
CH3CH2CO2H
A
B
C
D
CH3CHClCO2H
CH2ClCH2CO2H
CH3CH2CO2H
CH3CHClCO2H
weakest
CH3CH2CO2H
CH3CH2CO2H
CH2ClCH2CO2H
CH2ClCH2CO2H
16 Why is chloroethanoic acid, CICH2CO2H, a stronger acid than ethanoic acid?

A Chlorine releases electrons and destabilizes the CICH2CO2- anion.
B Chlorine releases electrons and stabilizes the CICH2CO2- anion.
C Chlorine withdraws electrons and destabilizes the CICH2CO2- anion.
D Chlorine withdraws electrons and stabilizes the CICH2CO2- anion.
[MI H1 / MCQ / Q19]
17 Which sequence shows the following compounds in order of increasing acidity?
Increasing acidity
A
B
C
D
C6H5CH2CO2H
C6H5CH2CH2OH
C6H5CH2CH2OH
C6H5CO2H
C6H5OH
C6H5OH
C6H5OH
C6H5CH2CO2H
C6H5CO2H
C6H5CH2CO2H
C6H5CO2H
C6H5OH
C6H5CH2CH2OH
C6H5CO2H
C6H5CH2CO2H
C6H5CH2CH2OH
[NYJC / MCQ / Q27]
18 Which of the following shows the correct order of increasing pK a?
X, W, Y, Z
B W, X, Y, Z
Z, Y, W, X
D Z, W, Y, X
[HCI / MCQ / Q30]
19 Arrange the following compounds in ascending (from smallest to largest) order of pK a.

CH3CH(I)COOH
CH3CH2COOH
CH3CH(Cl)COOH
CH3CH(F)COOH
(i)
(ii)
(iii)
(iv)
Carboxylic Acids
(iv), (iii), (i), (ii)
B (ii), (i), (iii), (iv)
20 Phenol has a pKa of 5.7.

Which one of the following has a lower pKa value?
A (CH3)3CCOOH
B
C
D
(i), (iii), (iv), (ii)
D (ii), (iv), (iii), (i)

[IJC / MCQ / Q17]
2,4,6-trimethylphenol
[NJC / MCQ / Q24]

21
A
B
C
D
In which sequence does the value of pK a decrease continuously?

CH3CO2H > CCl3CO2H > C2H5OH > C6H5OH
CCl3CO2H > CH3CO2H > C2H5OH > C6H5OH
C2H5OH > C6H5OH > CH3CO2H > CCl3CO2H
C6H5OH > C2H5OH > CH3CO2H > CCl3CO2H
[PJC / MCQ / Q25]
22 Which sequence shows the correct order of decreasing pKa value?

A CH3CH2OH > CH3COCl > CH3CO2H
B CH3CO2H
> C6H5OH
> CH3CH2OH
C C6H5OH
> CH3CO2H > C6H5CO2H
D CH3COCl
> CH3CO2H > C6H5OH
[TPJC / MCQ / Q30]
23 Which of the following, in aqueous solutions of equal concentration, has the lowest pH?
A chloroethanoic acid
B ethanoic acid
C propan-1-ol
D 2-chloropropan-1-ol
24 Three halogeno compounds can be synthesised from an organic compound K by the
following routes:
When compounds K, L, M and N (not necessarily in that order) are added to separate
portions of water, solutions are formed with pH values of 0.5, 2.5, 3.0 and 3.5.
Deduce which pH value is associated with each of K, L, M and N.
[MJC / MCQ /
Q22]
A
B
C
D
25 Bromine-containing organic compounds can be hydrolysed
under suitable conditions to produce the corresponding
bromide ion, Br-, which then can be reacted with aqueous
Carboxylic Acids
silver nitrate to form a cream precipitate.

A student investigated the mass produced by
hydrolysing 4 different bromine containing compounds,
W, X, Y, Z. Which of the following gives the correct structures
for W, X, Y, Z?
A
B
C
D
[MJC / MCQ / Q24]
26 Which sequence shows the wrong order of increasing ease of hydrolysis?
A C6H5Br < C6H5CH2Cl < CH3CH2COCl < CH3CH2I
B C6H5CH2Cl < C6H5CH2Br < CH3CH2I < CH3CH2COCl
C C6H5Cl < CH3COCH2Cl < C6H5CH2Br < CH3CH2I
D C6H5Br < CH3CH2Cl < C6H5CH2I < CH3CH2COCl
[VJC / MCQ / Q27]
27 Which materials are best used for the synthesis of
the following compound?
A CH3COOH and CH3NH2
B CH3CONH2 and CH3Br
C CH3COCl and CH3NH2
D CH3CONH2 and CH3OH
O
C
H 3C
CH 3
N
H
[ACJC / MCQ / Q30]

28 2-hydroxybutanoic acid, CH3CH2CH(OH)CO2H is treated with phosphorus pentachloride and
the organic product after isolation is added to cold water.
Which of the following is the formula of the main organic product obtained?
A CH3CH2CH(OH)COCl
B CH3CH2CHClCO2H
C CH3CH2CHClCOCl
D CH3CH2CH(OH)CO2H
29 Deuterium, D, is an isotope of hydrogen. Which of the following

3-step syntheses will provide compound A in good yield?
Carboxylic Acids
[MJC / MCQ / Q30]

30 Ethyl butanoate is used to make synthetic pineapple flavour.
CH3CH2CH2CO2C2H5
ethyl butanoate
Which set of reagents could be used to prepare ethyl butanoate in the laboratory?
A CH3CH2CH2CH2Cl, CH3CO2H, H2SO4
B CH3CH2CH2CH2OH, C2H5Cl, H2SO4
C CH3CH2CH2OH , C2H5CO2H, H2SO4
D CH3CH2CH2CO2H, C2H5OH, H2SO4
31 Which of the following sets of starting materials may be used for the preparation of phenyl
benzoate in the laboratory?
A C6H5OH, C6H5COOH, H2SO4(l)
B C6H5Cl, C6H5COCl
C C6H5OH, C6H5COCl, NaOH(aq)
D C6H5Cl, C6H5COCl, NaOH(aq)
[TPJC / MCQ / Q23]
32 Isopentyl acetate, CH3CO2CH2CH2CH(CH3)2 is prepared by reacting an excess of ethanoic
acid with isopentyl alcohol in the presence of sulfuric acid.
(CH3)2CHCH2CH2OH +
CH3COOH
CH3CO2CH2CH2CH(CH3)2 + H2O
The method to obtain the product, isopentyl acetate, would involve

I:
adding anhydrous sodium sulfate
II:
distillation
III:
separation of liquids using a separating funnel
IV:
shaking the mixture with NaHCO3
A
C
I, II, III
I, II, IV
B
D
II, III, IV
I, II, III, IV
[DHS H2 2011 / Q29]
33 A compound R, with molecular formula C9H10O2, is heated under reflux with aqueous sodium
hydroxide and the resulting mixture then cooled and acidified with dilute sulphuric acid. The
Carboxylic Acids
final products include a compound that turns blue litmus solution red, and another which
gives a purple colouration when tested with aqueous iron(III) chloride. What could R be?
A
C6H5OCOCH2CH3
B C6H5CH2OCOCH3 C C6H5OCH2COCH3 D C6H5CH2CH2COOH
34 When ethyl ethanoate undergoes hydrolysis with dilute sulphuric acid in the presence of
H218O, a mixture of two products is formed. Which of the following pairs correctly gives the
structures of the two products?
A CH3CO18OH and CH3CH218OH
B CH3COOH and CH3CH218OH
C CH3C18OOH and CH3CH2OH
D CH3CO18OH and CH3CH2OH
35 Which of the following substances will yield an alcohol upon being heated under reflux with
aqueous sodium hydroxide?
A CH3CH2NH2
B CH3CH2CO2CH3
C CH3CH=CH3
D C6H5Br
[TJC / MCQ / Q23]
36 Which one of the following is formed when the compound V is refluxed with an excess of
aqueous alkali?
A
B
compound V
C6H5CO and OC6H4CO
C
C6H5O and OC6H4CO2
C6H5CO and HOC6H4CO2H
D
C6H5OH and HO2CC6H4CN
[IJC 2011 / MCQ / Q28]
37 What are the products formed when compound J,

with dilute sulphuric acid?
A
HO
HO2C
C
D
CH3OCO
OCOCH3
is heated
OH
and CH3CO2H
CO2H
HO
and CH3OH
CO2H
CH3CH2OH ,
CH3OH,
HO2C
and HCO2H
OH
and CH3CO2H
Carboxylic Acids
38 Compound Y is boiled with aqueous sodium hydroxide and the resulting mixture cooled and
acidified with dilute sulphuric acid. The final products include a compound C 3H6O2 and an
alcohol. This alcohol gives a positive iodoform test. What is the formula for compound Y?
A CH3CH2CO2CH3
B CH3CH2 OCOCH3
C CH3CH2CO2CH2CH3
D HOCH2CH2 CO2CH2CH3
[TPJC / MCQ / Q24]
39 Which of the following statements is correct with regards to the conversion of compound B
to compound D?
A The conversion involves, in sequential order, an elimination reaction followed by an

esterification reaction.
B The conversion involves, in sequential order, a substitution reaction followed by an
addition reaction.
C The first step must consist of the conversion of compound B into an alkene.
D The second step requires the use of ethanoic acid.
40 Cyfluthrin is a synthetic pyrethroid insecticide that has both
contact and stomach poison action. It is a nonsystemic chemical used to control ants, cockroaches,
mosquitoes and many others.
What are the likely organic products from the reaction of
cyfluthrin with an excess of boiling aqueous NaOH?
A
D
[MJC / MCQ / Q28]
Carboxylic Acids
A
B
C
D
1, 2 and 3
are correct

are correct
are correct
1 only is
correct
1 In which of the following two-stage syntheses could a nitrile be the intermediate (X, Y or Z) ?
1 CH3CH2CH2Br X CH3CH2CH2COOH
2 CH3CH2CH2CH2OH Y CH3CH2CH2CH2CH2OH
3 CH3CH2I Z CH3CH2NH2
[NYJC / MCQ / Q37]
2 Which of the reagent/s added will produce similar observation when added to these two
compounds?
1 PCl5
Na
Acidified KMnO4 / reflux

[MI H1 / MCQ / Q29]
3 Which of the following statements is/are true for HOCH2CO2H and H2NCH2CO2H?
1 Both react with aqueous sodium hydroxide.
2 Both form zwitterions.
3 Both are insoluble in water.
[TJC / MCQ / Q37]
4
Malic acid, HO2CCH(OH)CH2CO2H, is found in some fruits. Which properties does malic
acid have?
1 Its molecule contains a primary alcohol group.
2 It can form esters with both ethanoic acid and with ethanol.
3 1 mole of malic acid will react completely with 3 moles of sodium metal.
5 Compound G is found in bananas and compound H in pears.
Which statements are correct?

1 G and H are structural isomers.
2 G and H can be hydrolysed in acidic and basic medium.
3 G and H have identical physical properties.
Carboxylic Acids
In which of the following pairs is the Ka of the first compound greater than the Ka of the
second compound?
1
2
3
CH3CH2COOH and CH3CH2OH

Cl
CH3CHCOOH
and CH3CH2COOH
CH3CH2CH2COOH and CH3CH2COOH
Which of the following correctly lists the compounds in order of decreasing acidity?
1
COOH
NO2
OH
3
CH3CCl2COOH, CH3CHClCOOH, CH3CH2COOH

CH3
OH
OH
CH3
OH
OH
Cl
OH
OH
OH
[SRJC / MCQ / Q39]
An unknown compound is refluxed with aqueous sodium hydroxide solution. The product is
acidified with nitric acid and aqueous silver nitrate solution is added. A precipitate is
observed. Which of the following could be the compound?
1 CH3CH2COCl
2 CH2BrCO2H
3 CH3I
9 Which of the following will yield an organic compound containing deuterium? (D = 2H)
1
2
3
[NJC / MCQ / Q40]

10 X, Y and Z are three different three-carbon compounds. X and Y react together to form an
ester. X and Z also react to give the ester as X and Y but much less readily. Compound X
could be
1 propan-2-ol
2 propanoic acid
3 propanoyl chloride
[YJC / MCQ / Q39]
Carboxylic Acids
11
Benzocaine and menthol are local anaesthetics used in sunburn ointments

and skin lotions. Their structures are
shown below. Which of the following
reagents and conditions can be used to
distinguish between these two
compounds?
1 Aqueous bromine in the dark
2 Ethanoyl chloride at room temperature
3 Hot acidified aqueous potassium manganate(VII)
[PJC / MCQ / Q38]
12 Which of the following statements are true for the compound below?
1 It is a non-planar compound.
2 When boiled with aqueous sodium hydroxide, it is converted to
3 It will react with 2,4-dinitrophenylhydrazine at room temperature.

[PJC / MCQ / Q39]
13 Fluorescein reacts with bromine to form 4, 5dibromofluorescein which
gives lipstick an orange colour. The structure of 4, 5dibromofluorescein
is show below. Which of the following statements are true for
4, 5dibromofluorescein?
1 It is likely to be hydrolysed by dilute hydrochloric acid.
2 It exhibits optical isomerism.
3 It undergoes nucleophilic substitution with aqueous sodium hydroxide.
[VJC / MCQ / Q38]
14 What would be the products formed when the following compound is
boiled with aqueous sodium hydroxide?
1 CH3CH2OH
2 CH3CH2O-Na+
3 ClCH2CH2COO-Na+
Carboxylic Acids
1
(a)
(b)
(c)
CH(CH3)2CN can be converted to 2-methylpropanoic acid.

State the reagents and conditions for the conversion.
Which is a stronger acid? 2-methylpropanoic acid or 2-chloropropanoic acid? Why?
Describe a simple chemical test to differentiate 2-chloropropanoic acid and 2-chlorobenzoic
acid.
[MI / II / Q7 ]
Tartrate ion is the conjugate base of the organic acid tartaric acid, that is used in
vinegar.
(i) When tartaric acid is heated in the presence of hot concentrated sulphuric
acid, two different organic products A and B of molecular formula C4H2O4
and C8H8O10 are formed.
Suggest the structural formula for products A and B.
2
(ii) State and describe the two types of hybridisation present in the C atom of the tartaric acid
molecule.
[MJC / II / Q3 d iv ]
3 Suggest a chemical test to distinguish between the
following pairs of organic compounds.
[NJC / II / Q3 c i ]
4 Methanol can be oxidized to methanoic acid.
(i) Write an equation for the oxidation of methanol to form methanoic acid.
(ii) Describe and explain how the acidities of methanol, methanoic acid and chloromethanoic
acid compare with each other.
[NYJC / II / Q3 b ]
5
Paracetamol is the active drug ingredient used to relieve headache, fever and flu. It was first
synthesised from 4-nitrophenol by Harmon Northrop Morse in 1878 and was commercially
produced and marketed in 1955. The structure of paracetamol is given below:
(a) Suggest a pathway to synthesise paracetamol from 4-nitrophenol .
Two other common drugs used to relieve headache, fever and flu are
aspirin and pseudoephedrine. The structural formulae, molar masses and
melting points of paracetamol, aspirin and 4-nitrophenol are given below.
Carboxylic Acids
(b) Suggest a reason for the lower melting point of aspirin as compared to 4-nitrophenol.
(c) Describe one simple test-tube reaction you could use to distinguish aspirin from
pseudoephedrine. State the reagents conditions and observations that can be seen.
[PJC / II / Q7 a, d, e ]
6 Compound Y can be synthesized from ethene in a 2-step process as follows:
I
CH2=CH2
II
X
O
C
O
OCH2 CH2 O
Y
(i) Suggest reagents and conditions for steps I and II.
(ii) Draw the displayed formula for the intermediate X.
[SRJC H1 / IIB / Q3 b ]
7
Lidocaine is a common local anesthetic drug used topically to relieve itching, burning and
pain from skin inflammations.
Using simple molecules like 2,6-dimethylphenylamine, ammonia and chloroethane,
lidocaine can be synthesized as shown below.
(i) Draw the structures of W and Z in the boxes below.
(ii) Suggest the structure of lidocaine.
(iii) Do you foresee any problem in the synthesis of Z? If yes, explain why.
CH3
CH3
NHCOCH2Cl
NH2
+
CH3
Y+Z
heat in a sealed
tube to give
lidocaine
NH3
+ CH3CH2Cl
heat in a
sealed tube
Z (C4NH11)
CH3
[TJC / II / Q5 c ]
0.025 mol of a hydrocarbon X was combusted completely to produce 4.4 g of carbon dioxide
gas and 1.35 g of water.
1 mol of X can react with 2 mol of hydrogen gas. When X reacted with acidified potassium
manganate(VII), the latter was decolourised and compound Y, C2H2O4, was formed as one
of its products. Y reacted with Na2CO3 to give a colourless, odourless and acidic gas. Y
reacted with 2 mol of CH3OH under suitable conditions to form Z, C4H6O4.
Determine the molecular formula of the hydrocarbon X, suggest and explain how you arrive
at the structures for X, Y and Z.
Carboxylic Acids
[TJC H1 / IIB / Q6 d ]
9
CH3CH2CO2H CH3CH2CH2OH
CH3CHCO2H
Cl
Arrange the above three compounds in increasing order of acidity and explain your answer.
[TJC H1 / IIB / Q7 a iii ]
10 Ferulic acid, which can be used as antioxidant, is found in seeds CH3O
of plants such as wheat and rice. It has the structure as shown:
State what you would observe and give the structural formula of
HO
the organic product when ferulic acid reacts with the following
reagents: Aqueous bromine, Ethanoyl chloride, Hot acidified
potassium manganate(VII)
COOH
State what you would observe and give the structural formula of the organic product when
ferulic acid reacts with the following reagents: PCl5
[TPJC / II / Q8 a ]
11 Use the information below to identify the compounds H to I. Explain your reasoning.
H and I each has the molecular formula C 2H4O2. H has an acrid (sharp) smell whereas I
has a fruity aroma. H reacts instantaneously with cold aqueous sodium hydroxide but I
reacts only when heated under reflux with aqueous alkali.
[VJC H1 / IIB / Q7 a iii ]
CH3O
COOH
12 Ferulic acid is an active ingredient in the Chinese herb Danggui.
Its structure is given below. [The CH3O group can be considered
relatively inert]
HO
(a) Ferulic acid exists as a pair of geometric isomers. Draw diagrams
to illustrate these isomers
(b) When gaseous hydrogen chloride is reacted with Ferulic acid, the products exhibit a different
type of stereoisomerism.
(i) Name and define the new type of stereoisomerism exhibited.
(ii) Draw diagrams to illustrate the isomerism you have described in (i).
(c) Ferulic acid is observed to be relatively soluble in water.
(i) Explain its solubility in water with the aid of a diagram.
(ii) Will Ferulic acid be more or less soluble in aqueous sodium hydroxide? Give your
reasoning.
(d) Draw the structures of the organic products formed when Ferulic acid reacts with the
following reagents:
(i) Aqueous bromine
(ii) Cold dilute manganate(VII) ions
(iii) Hot acidified manganate(VII) ions
(iv)Lithium aluminium hydride
(v) Benzoyl chloride
(vi) Thionyl chloride, SOCl2
[YJC / II / Q4 ]
Carboxylic Acids
Essay Questions
1
(i) Explain the differences in Ka values between the 3 compounds shown below.
(ii) The pKa of the acid,
is 4.8 where Y is a substituent. Predict the
product(s) formed when Cl2 is added to

dark. Explain your answer.
in the presence of FeCl3 in the

[IJC / III / Q4 c ]
Na2CO3 can be also be used to distinguish between carboxylic acids and alcohols. However,
this is not possible for propanoic acid and 2-hydroxypropanoic acid since both are carboxylic
acids.
(i) The melting points of propanoic acid and 2-hydroxypropanoic acid are 21 oC and 53 oC
respectively. Explain the difference in the melting points of these two acids.
(ii) Suggest chemical reagents and the conditions to distinguish both the monobasic acids.
Describe your observations for both the acids.
[PJC / III / Q2 c ]
3
(a) 7.8 g of ethanal reacts with 5.0 g of hydrogen cyanide in the presence of a trace amount of
sodium cyanide at 10 20 C to give 12.0 g of 2-hydroxypropanenitrile.
(i) Calculate the percentage yield of 2-hydroxypropanenitrile in this reaction.
(ii) Explain why 2-hydroxypropanenitrile has no effect on polarised light even though it contains
a chiral carbon.
(iii) -Hydroxy acids (AHAs) are naturally occurring carboxylic acids which are well-known for
their use in the cosmetic industry. Lactic acid, HOCH(CH 3)COOH, is an AHA can be formed
from 2-hydroxypropanenitrile. Write a balanced equation for this reaction, stating clearly the
reagents and conditions.
(b) Suggest methods by which the following compounds could be distinguished from each other
by chemical tests.
(i)
NHCOCH2
Br
and
OCOCH2
Cl
(ii)
and
(c) State and explain the relative solubility of 2-aminobenzoic acid and 4-aminobenzoic acid in
water.
Carboxylic Acids
NH2
H2N
COOH
2-aminobenzoic acid
4(a)
COOH
4-aminobenzoic acid
[SRJC / III / Q4 ]
A lethal combination of the following three prescriptive drugs simultaneously can cause
death. They are chloral hydrate, acetaminophen and meprobamate. The structures of
these three drugs are as shown:
Cl
Cl
OH
Cl
H
N
O
HO
acetaminophen
chloral hydrate
O
O
H2N
CH3
OH
NH2
meprobamate
Suggest chemical tests to identify two of the above drugs (namely acetaminophen and
meprobamate). You must give a positive test for each drug stating observations as well
as essential reagents and conditions.
(b)
You are given the following scheme of reactions.

CO2H
CH2OH
A
HO
HO
PCl5
B
HO
CONHCH2CH2
OH
(i) Draw the displayed formula of compound C.

(ii) Give the synthetic route, involving not more than three steps, from A to B. In your answer,
suggest reagents and conditions involved in each step.
Carboxylic Acids
(iii) Suggest a reagent together with the condition, which can be used to modify the chemical
structure of compound D, to make it water soluble.
[TPJC / III / Q4 a i, b ]
5
Compound A can absorb ultraviolet rays and is used in the production of skin cream. Its
structural formula is shown below:
O
CH3O
CH
CH
1. NaOH
HO
CHO
2. CH3I
Compound A
CH3O
CH2(CH2)3CH3
CHO
Step I
Step II
CH3O
Compound A
CH=CHCOOH
Step III
State the reagents and conditions for the reaction in Step III.
Suggest the mechanism of Step I.
[YJC / III / Q3 c iii ]
6
Compound X has the molecular formula C 4H6O2. X reacts with hydrogen cyanide to form Y,
C6H8O2N2. X also reacts with hot acidified potassium dichromate(VI) solution to produce Z,
C4H6O3. 2.50 g of Z (Mr = 102) was dissolved in 250 cm 3 of water. 25.0 cm3 of the solution
required 24.50 cm3 of 0.100 mol dm-3 of sodium hydroxide for complete neutralisation.
(i) Calculate the number of moles of Z that will be neutralised by one mole of sodium
hydroxide. Hence suggest one structural formula of X. Identify compounds Y and Z.
(ii) Draw one isomer of X that behaves like X. Label the isomer W.
(iii) Suggest one simple chemical test that can used to distinguish X from W. State the reagents,
reaction conditions and observations.
[YJC / III / Q5 d]
Nitrogen Compounds
7. Nitrogen
1 A nitrile X undergoes the following two reactions:
What would be produced when the products from the two reactions are mixed together?
A [ CH3CH2NH3+ ] [ O2CCH3 ]
B [ CH3CH2NH3+ ] [ O2CCH2CH3 ]
C CH3CONHCH2CH3
D CH3CH2CONHCH2CH3
[AJC / MCQ / Q28]
2
Neotame is an artificial sweetener made by NutraSweet that is

between 8,000 and 13,000 times sweeter than sucrose.
Which of the following is true about neotame?
A It is optically inactive.
B It can exist as a zwitterion in solution.
C Two products are obtained upon heating with aqueous NaOH.
D It decolorizes aqueous bromine in the absence of light.
[IJC / MCQ / Q25]
3 With what reagent would phenylamine and phenol give a similar reaction?
A Br2
B HCl (aq)
C Na metal
D NaOH (aq)
[MI / MCQ / Q28]
4 Aspartame is a sweetener commonly used in diet soft drinks and is provided as a table
condiment.
Aspartame
What are produced when aspartame is heated with aqueous sulphuric acid?
A
B
[MI / MCQ / Q30]
Nitrogen Compounds
When aqueous bromine is added to a solution of phenylamine, the colour of the bromine
disappears. Which of the following statements is true?
A
B
C
D
The mechanism is electrophilic addition.

The solution gets more acidic.
The NH2 group of phenylamine is substituted by Br.
Bromine forms a colourless complex with phenylamine.
[TJC / MCQ / Q30]
3-aminobenzoic acid can be produced from methylbenzene in three steps.
What is the best method for this synthesis?

A
Step 1
Dilute H2SO4, K2Cr2O7,
heat
Dilute H2SO4, KMnO4,

heat
Concentrated HNO3,
Concentrated H2SO4,
heat
Concentrated HNO3,
Concentrated H2SO4,
heat
Step 2
Concentrated HNO3,
Concentrated H2SO4,
heat
Concentrated HNO3,
Concentrated H2SO4,
heat
heat
Step 3
Concentrated HCl, Sn,
heat

heat

heat

heat
heat
[ACJC H2 2011 / Q19]
4aminobenzoic acid, commonly known as PABA, is used as a drug against fibrotic
Nitrogen Compounds
skin disorders, and can also be used in the treatment of irritable bowel syndrome.
H2N
COOH
PABA
Which of the following is a possible means of its preparation?
A
CN
CN
CH3
CH3
conc HNO3
Sn, conc HCl
conc H2SO4
H2O / H+
H2O / H+
heat
conc HNO3
heat
conc H2SO4
conc HNO3
Sn, conc HCl
conc H2SO4
Sn, conc HCl
KMnO4 / H+
heat
KMnO4 / H+
conc HNO3
heat
conc H2SO4
Sn, conc HCl
[AJC H2 2011 / Q29]

8
Consider the aromatic amine, phenylamine. Which of the following statement is true?
A It undergoes electrophilic addition
B It is more basic than ethylamine
C It gives no reaction with ethanoyl chloride
D It reacts with aqueous bromine to give a white precipitate
[YJC / MCQ / Q29]
9 Four students suggested reagents that can differentiate the following two compounds.
Which suggested reagent is most suitable?

A
thionyl chloride
neutral iron(II) chloride
bromine water
sodium carbonate
[VJC H2 2011 / Q25]
Nitrogen Compounds
10 Which one of the following shows the given ions arranged in order of increasing pKa values?
A
B
C
D
NH4+, C6H5NH3+, (CH3CH2)2NH2+

C6H5NH3+, NH4+, (CH3CH2)2NH2+
(CH3CH2)2NH2+, C6H5NH3+, NH4+
(CH3CH2)2NH2+, NH4+, C6H5NH3+
[VJC H2 2011 / Q27]
11 Consider the four compounds listed below:

I : CH3CH2CH2NH2 II : FCH2CH2CH2NH2 III : ClCH2CH2CH2NH2 IV : CH3CH2CONH2
Which of the following sequence arranges the compounds in increasing pK b?
A
IV, III, II, I
B III, II, I, IV
II, III, IV, I
D I, III, II, IV
[TJC / MCQ / Q28]
12 Which of the following statements explains why C6H5NH2 is a weaker base than CH3NH2?
A C6H5NH2 is less volatile than CH3NH2.
B The methyl group in CH3NH2 is electron withdrawing, hence stablising the ion formed on
dissociation.
C The electron rich C6H5 group in C6H5NH2 is electron releasing.
D The lone pair of electrons on the nitrogen in C6H5NH2 is delocalized over the benzene
ring.
[TPJC / MCQ / Q29]
13 Which sequence shows the nitrogen compounds in increasing order of basic strength?
least basic
most basic
C
D
[AJC / MCQ / Q29]
14 Why do proteins have a buffering effect in cells?
A They are non-polar.
B They are amphoteric.
C They form colloidal solutions.
D They are a major component of cell surface membranes.
[NYJC / MCQ / Q29]
Nitrogen Compounds
15 Amino acids have comparatively high melting points when compared with other organic
compounds of similar mass. Which of the following statements best explains this
observation?
A In the solid state, amino acids are held together by strong hydrogen bonds.
B In order to melt an amino acid, strong covalent bonds are broken.
C Amino acids are held together by ionic bonding.
D Amino acids are held in fixed positions in a solid lattice.
[HCI / MCQ / Q27]
16 Which statement is false about an -amino acid?
A
It exists as a solid with high melting point.
B
The amino group and carboxylic acid group are attached to the same carbon.
C
They may exhibit optical isomerism.
D
It can behave as a strong acid or base, and is thus amphoteric.
[MI H2 2011 / Q29]
17 The structures of some amino acids are shown below:
H
H2N
COOH
H2N
COOH
(CH2)4
(CH2)2
NH2
COOH
glutamic acid
lysine
H
H 2N
COOH
H2N
COOH
CH
H3C
phenylalanine
CH3
valine
Which of the following pairs of amino acids are likely to be found on the exterior of a
globular protein?
A glutamic acid and lysine
C
glutamic acid and valine
B valine and phenylalanine
D
lysine and phenylalanine
[IJC H2 2011 / Q30]
Nitrogen Compounds
18 Tyrosine is one of the 20 amino acids that is used by cells to synthesise proteins, and
was first discovered in cheese.
O
OH
HO
NH2
Tyrosine
Which of the following types of reaction will Tyrosine not undergo?

A reduction
B nucleophilic addition
C nucleophilic substitution
D electrophilic substitution
[PJC H2 2011 / Q29]
19 A sample of serine is dissolved in a buffer solution of pH 12.
Which form will be predominant at this pH?

A
D
[AJC / MCQ / Q30]
20 An amino acid, Valine, in the primary structure of normal haemoglobin

has the following structure. Given that the isoelectric point of Valine is
5.96, which of the following shows the correct structure of the Valine at pH 6.30?
A
B
D
[IJC / MCQ / Q13]
21 The pKa values of C1 carboxyl group, C2 carboxyl group, and amino group of aspartic
Nitrogen Compounds
acid are 1.88, 3.65, and 9.60, respectively. Its structure is as shown below:
O
HO
C1
C2
O
OH
NH2
The predominant form of aspartic acid at pH 7 is

O
A
B
O
C1
C2
O
C1
O
HO
NH3
NH3
D
OH
O
O
C2
C1
C2
NH2
C
HO
O
-
C1
C2
NH3
[MI H2 2011 / Q28]

22 Electrophoresis is an analytical method frequently used in molecular biology to analyse
and separate proteins and amino acids. Amino acid samples are placed in a gel slab
containing a buffer. The ends of the gel slab are connected to charged electrodes and
the charged amino acid particles move towards the oppositely charged electrodes.
Which amino acid will move most readily towards the anode at pH 10?
NH2
HN
O
N
H
O
OH
HO
OH
NH2
NH2
OH
OH
HO
NH2
OH
NH2
[TJC H2 2011 / Q24]
Nitrogen Compounds
23
The amino acids, glutamic acid and glutamine, can react with each other to formamide
linkages.
What is the maximum number of different compounds, each containing one natural
amide linkage that can be formed from one molecule of glutamine and one molecule of
glutamic acid?
A 2
B
3
C
4
D
5
[ACJC H2 2011 / Q22]
24 Aspartame is widely used as a sweetener in canned drinks.
H2N
CH CONHCH CO2CH3
HO2CCH2
CH2
Aspartame
When Aspartame is treated with LiAlH4 in dry ether, what is the final product obtained?
A
H2N
CH CH2NHCH CH2OH
HOCH2CH2
CH2
H2N
CH CONHCH CH2OH
HOCH2CH2
CH2
H2N
CH CH2NHCH CO2CH3
HO2CCH2
CH2
H2N
CH CONHCH CH2OH
HO2C CH2
CH2
[PJC H2 2011 / Q30]
Nitrogen Compounds
25 Gastrins are heptadecapeptide (17 amino acid units) hormones that stimulate the secretion
of gastric acid in the stomach of mammals. On hydrolysis of gastrins, the following 4 peptide
fragments were isolated.
gly-trp,
leu-glu-glu-glu-glu-ala-ala-try,
glu-gly-pro-trp,
met-asp-phe
C-terminus analysis of the heptatdecapeptide yields a phe residue while N-terminus analysis
yields a glu residue. Based on the information above, suggest a primary structure for the
heptatdecapeptide and the number of peptide bonds it contains.
A
B
C
D
[MJC / MCQ / Q19]
26 Partial hydrolysis of a decapeptide (containing 10 amino acid residues) using an enzyme
yielded the following tripeptide fragments:
HisTyrArg,
TyrArgThr,
GlnThrAsp,
AspArgHis,
ArgHisTyr,
ThrArgGln
Which of the following is the amino sequence of the decapeptide?

A
HisTyrArgThrAspArgGlnGlnThrArg
B
ThrArgGlnThrArgHisTyrThrAspArg
C
ThrAspArgGlnThrArgThr ArgHisTyr
D
ThrArgGlnThrAspArgHisTyrArgThr
27 In the study of a polypeptide structure of Z, it was digested using two different enzymes.
The fragments obtained were then separated using electrophoresis. Analysis of the
fragments from each digestion gave the following results:
Fragments using first enzyme:
tyr-leu-leu
tyr-ala
gly-asp-pro
asp-pro
Fragments using second enzyme:

leu-tyr
asp-pro-gly
ala
asp-pro-tyr-leu
Deduce the possible sequence of Z.

A
B
C
D
asp-pro-tyr-leu-ala-leu-tyr-asp-pro-gly
asp-pro-gly-asp-pro-tyr-leu-leu-tyr-ala
gly-asp-pro-asp-pro-tyr-ala-tyr-leu-leu
ala-asp-pro-gly-asp-pro-tyr-leu-leu-tyr
[SRJC H2 2011 / Q30]
28 The presence of a quaternary structure in haemoglobin is confirmed by the presence of
Nitrogen Compounds
A
B
C
D
four subunits in a molecule of haemoglobin.

ionisable amine groups on the side chain.
interactions between the side chains about a polypeptide chain.
an active site known as a haem group covalently bound to the protein.
[MI H2 2011 / Q30]
29 The following diagram shows the structural components of oxyhaemoglobin, the oxygenated
form of haemoglobin,
Which of the following statements about oxyhaemoglobin is correct?

A
B
C
D
Each oxyhaemoglobin holds only one oxygen molecule.

Oxyhaemoglobin comprises two -helices and two -sheets.
A covalent bond helps to hold the haem group in each subunit.
The subunits are held together by hydrogen bonds between the peptide linkages
[RI H2 2011 / Q30]
30 Which of the following proteins will not retain its primary structure?
A
B
C
D
Beating the egg white using a glass rod.

Boiling insulin with dilute hydrochloric acid.
Adding drops of tetrachloromethane to collagen.
Mixing Ca2+ ions to casein.
[IJC H2 2011 / Q29]
Nitrogen Compounds
A
B
C
D
1, 2 and 3
are correct
1

are correct
are correct
1 only is
correct
The structure below shows part of a protein. What type of interactions involving the side
chains of the above protein segment could be responsible for the maintenance of the
tertiary structure of the protein?
[YJC / MCQ / Q40]

1 van der Waals forces
2 hydrogen bonding
3 disulphide bonds
2 The structure of the herbicide Karbutilate is shown below.
What would be formed by prolonged boiling of Karbutilate with aqueous sodium hydroxide?
1
2
3 H2NC(CH3)3
[AJC / MCQ / Q40]
Nitrogen Compounds
Polyacrylonitrile is a polymer used in making carpets and upholstery. The structure of the
monomer of polyacrylonotrile is shown below.
Monomer of polyacrylonotrile
Which of the following statements about the monomer are correct?

1 When reacted with HBr, the product formed can rotate the plane of polarized light.
2 When reduced with LiAlH4, the product is ethylamine.
3 Water is eliminated when it undergoes polymerization.
[MI / MCQ / Q40]
4
Folic acid is a form of the water-soluble

Vitamin B9 that occurs in food such as
liver, kidney, and green leafy vegetables.
Which of the following will react
completely with two moles of folic acid?
1 2 mol of dilute HCl at r.t.p.
2 4 mol of PCl5 at r.t.p.
3 8 mol of boiling aqueous NaOH
[MJC / MCQ / Q39]
5 Part of the amino acid chain in a polypeptide is as follows:
Which of the following compounds is/are obtained when the polypeptide is hydrolysed?
1
2
3
[IJC / MCQ / Q40]
6 Which of the following statements regarding the denaturation of a protein is true?
1 The flavour and texture of foods may be affected.
2 Renaturation is possible if the denatured protein precipitates out.
3 The amino acid sequence is altered.
[NJC / MCQ / Q38]
7 Precipitation is widely used in downstream processing of biological products, such as
proteins. For example, in the biotechnology industry, protein precipitation is used to eliminate
contaminants commonly contained in blood. Which of the following reagents can be used to
induce protein precipitation?
1 0.1 mol dm-3 aqueous sodium hydroxide
2 a saturated aqueous solution of (NH4)2SO4
3 0.1 mol dm-3 Pb(NO3)2
[IJC / MCQ / Q38]
8
Terfenadine alleviates sea-sickness and asthma. Its structure is shown below.
Nitrogen Compounds
What deductions can be made from the structure of Terfenadine?

1 One mole of Terfenadine will liberate two moles of HCl on reaction with two moles of
PCl5
2 Terfenadine reacts with concentrated sulphuric acid at 180 C to form a product that
decolourises aqueous Br2 at room temperature
3 Terfenadine reacts with dilute aqueous HCl to form a salt
[YJC / MCQ / Q38]
1
R group interactions are needed to hold the tertiary structure of a protein in its necessary
shape. Identify which type of R group interaction is destroyed by extreme pH changes when
a protein is denatured. Explain in chemical terms how this R group interaction is destroyed.
[AJC / II / Q5d ]
2 The enzyme phospholipase A2, from rattlesnake venom, is a biological catalyst used in the
hydrolysis of phospholipids as shown below.
(a) Explain what you understand by the term catalyst.

(b) Suggest why the enzyme hydrolyses only one of the ester groups.
(c) Phospholipase A2 contains phenylalanine and serine residues.
The structures of the amino acids, serine and phenylalanine, are shown below.
Nitrogen Compounds
Suggest how the tertiary structure of the phospholipase A2 may be affected if all the
phenylalanine in the enzyme are replaced by serine, and explain why this might prevent the
enzyme from working.
[HCI / II / Q5 a, b, c ]
3 (a) The structural formulae of three amino acids are given below.
(i) Which amino acid when dissolved in water shows basic character?
Explain your answer.
(ii) Draw structural formulae for the dipeptides that can be formed between lysine and
serine.
(iii) Crystals of the simplest amino acid, glycine, NH 2CH2CO2H melt between 230oC to
235oC. Suggest why the melting point of glycine is higher than that of
hydroxyethanoic acid, HOCH2CO2H (m.p. 75-80oC).
(b) Partial hydrolysis of a tetrapeptide produces the following three dipeptides, as well as the
individual amino acids.
NH2CH(CH2CH2CH3)CONHCH(CH2CH2CH3)COOH
H2NCH(CH3)CONHCH(CH2CH2CH3)COOH
NH2CH(CH2CH2CH3)CONHCH(CH2Ph)COOH
Deduce the order in which the amino acids are bonded in the tetrapeptide, showing your
reasoning.
[IJC / II / Q9 b, c ]
4 Much research has been done in recent years investigating the exact nature of Spider silk.
The silk of a spiders web is at least five times as strong as steel. This can be attributed to
the secondary structure of proteins , specifically the pleated sheet.
(a) Draw a diagram, with displayed formula; showing two strands of a pleated sheet
structure of the protein, the formula of which is given below. Indicate clearly on the diagram
any type of interactions present between the two strands.
CHRNHCOCHRNHCOCHRNHCO
(b) Name another type of secondary structure that is predominant in DNA and briefly explain its
structure.
(c) A silk fibre is composed of many identical protein chains, which are made from the aminoacids such as glycine, glutamine and serine.
glycine
glutamine
serine
(i) Draw the zwitterionic structure of glutamine and account for the high solubility of the aminoacid in water.
Nitrogen Compounds
(ii) Amino acids can act as acids or bases. Write an equation to show the reaction between
serine and aqueous sodium carbonate.
(iii) Draw the structural formula of a tripeptide with the sequence gly-gln-ser, showing the
form which it would exist at pH 3.
(d) In a laboratory setting, hydrolysis of a small portion of Spider silk comprising of a
pentapeptide portion comprising of the 3 amino-acids stated in (c), produced the following
smaller tripeptide fragments.
NH2CH(CH2OH)CONHCH2CONHCH(CH2OH)COOH
NH2CH(CH2CH2CONH2)CONHCH(CH2OH)CONHCH2COOH
NH2CH2CONHCH(CH2OH)CONHCH(CH2CH2CONH2)COOH
(i) Suggest suitable reagents and conditions for the hydrolysis reaction.
(ii) Suggest a possible sequence for the primary structure of the pentapeptide portion of the
Spider silk.
(e) The Mr of a silk protein molecule is about 610,000. Assuming it is only made from glycine,
glutamine and serine in the proportion of 2 : 1 : 3 respectively, calculate the average number
of amino-acid residues in the protein chain.
[ Mr (glycine) = 75; Mr (glutamine) = 146; Mr (serine) = 105 ]
[MJC / II / Q5 ]
5 (a) The graph below shows the effect of temperature on the -helix structure of a polypeptide
chain found in a protein.
(i) In what level of protein structure is the -helix structure commonly found?
(ii) Name an example of a protein that is entirely made up of the -helix structure.
(iii) What type of bond helps to maintain the -helix structure?
(iv) Explain what happens to the -helix structure in proteins at a temperature above 60 oC.
(b)
(i) State the function of haemoglobin in the body, and state how it carries out this function.
(ii) In some illnesses, it is necessary to increase the rate of oxyhaemoglobin formation.
Suggest one method in which the rate of oxyhaemoglobin formation can be increased.
Explain your answer.
[NYJC / II / Q7 ]
6
(a) The diagram below shows the structure, at pH 7, of a fragment from a protein which contains
four amino acids, A, B, C, and D.
A
NHCHCONHCHCONHCHCONHCHCO
HOOCCH2
CH2SH
CH
CH3
CH2OH
CH3
(i) Draw the structure of the first amino acid, A, that could be obtained by hydrolysis of the
protein fragment.
Nitrogen Compounds
(ii) Which side-chains in the amino acids A to D are most likely to be involved in the denaturing
of proteins by changes in pH? Explain your answers, giving equation(s) or structure(s)
where possible.
(iii) Show, with diagrams, how the side-chains on amino acids B and D could be involved in the
maintenance of the tertiary structure of the protein.
(b) The white of an egg is about 88% water and 12% globular protein (by mass). When heated,
the egg white undergoes gross conformational changes. What happens to the structure of a
globular protein during these changes?
[TPJC / II / Q9 ]
7(a)
Electrophoresis is a technique used to identify different amino acids. In a particular
electrophoresis experiment, a piece of rectangular filter paper is soaked in an aqueous
solution of pH 3 and three amino acids labelled A, B and C are dotted onto the middle of the
paper. A potential difference is then applied. After a while, the paper is sprayed with a
colouring chemical to locate the amino acids.
A
At the start of experiment

At the end of experiment
(i) The structures of the three amino acids being investigated in the experiment are shown
below.
Draw the corresponding forms of the amino acids at pH 3 in the corresponding boxes.
CH3
CH2NH2
HOOC C CH2COOH
H3C C CH2COOH
H3C C CH2COOH
NH2
CH3
NH2
NH2
Q
(ii) Which of the three amino acids P, Q or R in (i) corresponds to dot B at the end of the
experiment? Briefly explain your reasoning.
(b) Arrange the compounds CH3NH2, (CH3)2NH and CH2BrNH2 in order of increasing base
strength. Explain your answer.
[YJC / II / Q5 c, d ]
Nitrogen Compounds
Essay Questions
1
The table below gives the numerical Kb values of CH3NH2, NH2OH and C6H5NH2. Suggest
reasons for the different Kb values of these compounds.
[MJC / III / Q5 b ]
2
(a)
(i)
(ii)
(b)
Proteins are naturally occurring polypeptides of relative molecular mass greater than 5000
and are essential for life in all living things and have many biological functions in our bodies.
The protein molecules are large and are responsible for growth, repair and maintenance of
the body. The building blocks of proteins are amino acids, such as leucine and glutamine.
Many proteins contain significant amounts of secondary structures as -helix structures or pleated sheets.
What is meant by the secondary structure of a protein?
Sketch a diagram showing two strands of a -pleated sheet structure, indicating the
essential features on your diagram. You may choose to use the general formula of a primary
structure as shown below.
-CHRNHCOCHRNHCOCHRNHCOThe folding of the -structures in enzymes is caused by the interactions of the R groups.
Give simple examples of four different group interactions, illustrating each case with a
suitable formula for each R group concerned.
[PJC / III / Q1 a, b ]
3(a) (i)Explain what is meant by the primary structure of a protein.

(ii) Describe with the aid of a sketch, the structure of the -helix form of protein. Indicate how
the structure is stabilised, drawing the formula of the stabilising bonds.
(iii) The folding of the -helix structure in protein such as enzyme is caused by interactions of
the R groups. Give simple examples of the four different R group interactions, illustrating
each one with a suitable formula for the R group concerned.
(b) The enzyme chymotrypsin digests proteins or polypeptides at the carboxylic acid end of the
amino acid phenylalanine, phe. The following peptides were identified after digestion of the
polypeptide P with chymotrypsin, and subsequent separation.
asplysglyphe
lysvalarg
valphe
Another enzyme trypsin digests at the carboxylic acid end of lysine, lys. The following
peptides were identified after digestion of the same polypeptide P with trypsin, and
subsequent separation.
glyphelys
valarg
valpheasplys
Use the above information to determine the primary structure of polypeptide P. Justify your
answer.
(c) A sample of cows milk was diluted with distilled water and the resulting mixture was then
treated with a few drops of a weak acid. A precipitate was formed. Explain this observation.
[TJC / III / Q3 b, c, d ]
Nitrogen Compounds
4
(a) Suggest one simple chemical test which would enable you to distinguish the following pairs
of compounds. State reagent(s) and condition(s) and their corresponding observations.
NH2
H2N
CH2CH2CH3
O2N
CHCH2CH3
(b) Place the following compounds in the order of increasing K b value.

Explain your reasoning.
NH2
CH2NH2
(c) Trypsin and chymotrypsin are secreted by the pancreas to aid the digestion of proteins in the
small intestine. In the study of the primary structure of a polypeptide A, the following
fragments were obtained when A was digested using trypsin which cleaves peptide bonds at
the carboxyl end of phenylalanine (phe).
phe,
try-lys-gly-ala,
gly-lys-phe,
ser-lys-ala-phe
When A was digested using chymotrypsin which cleaves at the carboxyl end of lysine (lys),
the following fragments were obtained.
ala-phe-gly-lys,
phe-ser-lys,
gly-ala
phe-try-lys
Deduce the primary structure of A.
[TPJC / III / Q3 a i, b, c ]
5
(a) Explain the meaning of each of the following terms as applied to proteins, illustrating your
answer with one appropriate example:
(i) Denaturation
(ii) Quaternary structure
(b) Aspartame which is used as an artificial sweetener has the following
formula: Aspartame can be prepared through a series of reactions
staring with amino acids.
(i) Give the structural formula of the amino acids that could be used to
prepare aspartame.
(ii)
Describe the types of R group interactions that could exist for these amino acids.
(iii) Describe a simple chemical test by which you could identify one of the functional groups
in Aspartame.
[VJC / III / Q5 a, b ]
6
(a) The diagram below shows part of a protein formed from three amino acids
O H
O H2C
C C N C
H H
H2
C
CH2
H H
N C C N
O CH2SH
(i) Draw the structures of the three amino acids from which this part of the protein is formed.
(ii) Describe with the aid of diagrams if necessary, the secondary and tertiary structures of
protein.
Nitrogen Compounds
(iii) A protein can be denatured by the application of temperature above 40 oC. Explain how
denaturation of proteins occurs.
(b) Describe simple chemical tests (reagents, conditions, observations and equations) to
distinguish between the following pairs of compounds:
CHCH2Cl
CHCH2Cl
Cl
CH2NH2
and
H2N
CH2Cl
[YJC / III / Q4 b, c i ]

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Catholic Junior College

2014 JC2 MYE Topical

[AJC H2 2012 / Q20]

at the start of the

at the end of the

The structure of the product of the reaction is

[MI H2 2011 / Q22]

Which of the following could be the structure of X?

[HCI 2012 / Q16]

[HCI 2012 / Q17]

Outline the mechanism of the reaction of step V.

3. Suggest one simple chemical test which would

compounds. State reagent(s) and condition(s) and

Compound F can be formed when compound E undergoes bromination.

State the reagents and conditions for the reaction.

[TJC 12/ III / Q2c]

Is compound R optically active? Explain why.

Methylbenzene is also used to synthesize trinitrotoluene, TNT, according to the synthetic

Suggest reagents and conditions for Step 1.

[HCI 12/ III/ Q2(b)]

[AJC / MCQ / Q23]

[ACJC / MCQ / Q22]

The type of reaction mechanism shown above is

[MI H1 / MCQ / Q16]

[NJC H1 / MCQ / Q20]

CH3Br + C2H5I + 2Na

CH3CH2CH3 + NaBr + NaI

[SRJC 2011 / MCQ / Q24]

[TJC / MCQ / Q26]

[YJC / MCQ / Q24]

23 Dichlorodifluoromethane, CCl2F2, is a widely used aerosol propellants and as a refrigerant.

1 and 2 only 2 and 3 only

The formulae of two halogenoalkanes are given below.

[RCl] = x mol dm-3

[RCl] = 2x mol dm-3

[AJC / III / Q5 c iii ]

When a mixture of beryllium hydroxide pellets and ethanol is added to 2-chlorobutane, P, Q, R

A halogenoalkane, Z, with a labelled carbon, C, undergoes the following reaction:

Explain why chloroethane undergoes nucleophilic substitution but not chlorobenzene.

Which of the following statements about the two isomers is incorrect?

Which term describes this type of reaction?

A compound has the following structure. All of the following

6 A yellow crystalline compound X gives compound Y

[ACJC / MCQ / Q23]

O2N NO2 O2N NO2

[ACJC / MCQ / Q27]

[IJC / MCQ / Q16]

13 In which sequence is it correctly stated that the value of pK a decreases continuously?

15 2-methylpropan-1-ol can be converted into 2-methylpropan-2-ol as follows:

Which of the following sequences may be used for the conversion?

Which of the following statements is false?

[MJC H1 / MCQ / Q21]

Which of the following structural formulae is not a product of the pinacol

24 In a preparation of propene, propan-1-ol is added a drop at a time to a heated reagent P. The

[TJC H1 / MCQ / Q21]

25 Compound E, C8H9ClO2, gives compound F, C8H7ClO2, on mild oxidation. F gives a yellow

TPJC / MCQ / Q26]

[VJC / MCQ / Q22]

A hot HCl(aq) to form

C HCl in CCl4 to form

hot acidic KMnO4 to form

[VJC / MCQ / Q24]

C CO2 and HOOCCH2CH2COOH