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Q
:
Paart 11 Chemistry of
o Carbon
n Compou
unds
Naaming an
nd Isomerrisms
1. HKAL 19988 II Q5a
Consider the
t followingg compoundd F.
#(i)
(ii)
2. HKAL 19988 I Q4
Alcohol E has the struucture CH3CH
H(OH)C2H5.
a.
(i)
(ii)
W type of isomerism
What
i
caan be exhibitted by E?
(2 marrks)
b.
(i)
Draw the structure of three structural isomers of E, all of which are alcohols.
#(ii)
Describe how the reagent Zn/concentrated HCl can be used to distinguish E from the three structural
isomers.
(3 marks)
c.
On treatment with dilute H2SO4(aq), E gives mainly two isomeric compounds, F and G, both of which have
the formula C4H8. On treatment with bromine, both F and G give a product H with formula C4H8Br2.
(i)
(ii)
Characteristics
Explain why, in 1,2-dichloroethene, the carbon-carbon double bond cannot rotate freely.
(ii)
Explain why
(I)
(II)
5. HKAL 2010 I Q4
Dimethyl fumarate can be found in most leather products since it is commonly used as a mould inhibitor.
However, it was banned in Europe for all kinds of consumer goods in March 2009 because it was found to
cause skin allergies. Compound A is an isomer of dimethyl fumarate. The structures and melting points of
these two compounds are given below:
(a)
(i)
(ii)
Explain why the melting point of A is lower than that of dimethyl fumarate.
(3 marks)
(b)
Both dimethyl fumarate and A can be hydrolysed to their corresponding dicarboxylic acids, B and D.
(i)
(ii)
c.
d.
W
Would
the prooduct rotate a beam of plaane polarized
d light? Expllain your ansswer.
(i)
(ii)
W P and Q exhibit
Will
e
the saame chemicaal properties?? Explain your answer.
(3 marrks)
(ii)
One of these isomers is used to make terylene. Outline the reaction involved.
(iii)
On heating, one of the isomers gives a compound W, with formula C8H4O3. Give the structure of W.
(5 marks)
9. HKAL 1992 II Q7
A carboxylic acid P, with a relative molecular mass less than 100, contains C, 55.8%; H,7.0%; and O, 37.2%
by mass. An attempt to convert P to its methyl ester Q by prolonged refluxing of P with methanol in the
presence of aqueous H2SO4 gave the desired ester Q but with much of the starting material P unchanged.
a.
b.
Give the structures of four carboxylic acids having the molecular formula you determined in (a). Give
the systematic names for any one of the carboxylic acids and its methyl ester.
c.
Suggest, with explanations, two ways which would make the esterification go towards completion.
d.
Which has a higher boiling point, the carboxylic acid or its methyl ester? Explain your answer.
e.
stereoisomerism?
(3 marks)
CH3
CH3CH
CH3
CH
CH2CH=CH 2
b.
O
CH3CH2CH2-O-C-CH2CH2CH3
c.
O
CH3CH2-C-CHCH2CH3
OH
(3 marks)
(3 marrks)
10
(5 marks)
11
Ans: B
12
Elemental analysis data show that D has the following composition by mass: C 40.0%, H 6.7%
and O 53.3%.
(2)
#(3)
The infra-red spectrum of D shows, apart from the absorption of CH stretching near
2900 cm-1, a
strong and broad absorption around 3400 cm-1, and no appreciable absorption around 1700 cm-1.
(4)
(5)
D is highly soluble in water, and the solution does not decolorise bromine water.
(8 marks)
13
(i)
(ii)
(iii)
(I)
(II)
It is known that among the two stereoisomers, only B has stimulant activity while the other one
does not. Why?
(iv)
14
(ii)
Outline the mechanism and name the mechanistic steps of the reaction.
(iii)
Is the reaction of methane with chlorine an appropriate method for the preparation of dichloromethane?
Explain.
(5 marks)
(i)
(ii)
(iii)
15
(iii)
(i)
(iii)
16
(i)
(iii)
A student commented that J obtained from the above reaction is optically active. Do you agree with
the student? Explain.
(5 marks)
(i)
(iii)
B.
C.
D.
Ans: C
17
(1 mark)
25.
(i)
18
#(i)
The reactant for Step 1 is Br2. Propose a mechanism for the formation of A from buta-1,3-diene.
(ii)
#(iii)
Explain why the strength of neoprene can be improved after heating it with sulphur.
(8 marks)
27.
CH2=CHCO2CH3 CH3CH2CO2CH3
(1 mark)
M: Pd or Ni or Pt / H2
19
(ii)
KMnO4
H3C
CH3CH=CH2
OH
OH
(1)
(ii)
(2 marks)
CH3
(i)
G:
H3C
CH2CH3
Br
(ii)
H:
CH3CH2CH2OH
20
OH
CH3CH2CH2OH
H3C
CH3
H
(3 marks)
OH
OH
OH
(3 marks)
21
31. Outline chemical tests which would allow you to distinguish between the compounds in the following pairs.
Describe what you would observe in each case.
a.
COOH
(2 marks)
Add solution of NaHCO3 to the compound, C6H5COOH will react to give CO2 while the phenol C6H5OH will not.
b.
OH
CH3CH2CH2
CH3
CH3CH2CH2
CH3
CH2OH
C
CH3
(2 marks)
Warm the compounds with acidified K2Cr2O7.
The primary alcohol will turn the solution from orange to green while the tertiary alcohol will not.
c.
CH2OH
CH3
(3 marks)
Warm the compounds with acidified K2Cr2O7.
The primary alcohol will turn the solution from orange to green while the tertiary alcohol will not.
22
d.
CH2OH
OH
(4 marks)
e.
CH3CH2COCH2CH3
(3 marks)
f.
O
C
(2 marks)
23
(ii)
your calculation.
(3 marks)
24
LiAlH4
C7H14O
H2/Pd
C7H16O
T
Given that R exists as a mixture of geometrical isomers, S has a chiral carbon center, and T does not have any
chiral carbon center, deduce all possible structures of R, S and T.
(8 marks)
25
CH3CH2CH2OH
Cr2O72- / H+
CH3CH2CHO
heat
a side-product N (C6H12O2) was formed.
(i)
(ii)
(iii)
(i)
(ii)
(iii)
26
(1 mark)
#(ii) The indoor air quality (IAQ) standard for formaldehyde has been set at 0.10 ppm by volume.
Calculate the maximum allowable quantity of formaldehyde, in gram in a room of volume 200 m3 at
298 K and 1.01 105 N m-2.
(You may assume that formaldehyde behaves as an ideal gas.)
(iii)
Some indoor air purifiers remove formaldehyde by chemical means. Suggest one chemical for the
removal of formaldehyde with the formation of less harmful products.
(iv)
Name one other organic indoor air pollutant and suggest its source.
(7 marks)
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37.
a. HKAL 1994 II Q7
CH3CH=CHCH2CH2COOH
LiAlH4
(1 mark)
CH3CH=CHCH2CH2CH2OH
b.
CH3CH2CH2COCl
(1 mark)
(iv)
HOCH2CH2OH
OCH2CH2O
n
(1 mark)
28
CO2H
CH3
CH3
3-methylbenzoic acid
N,N-diethyl-3-methylbenzamide
(2 marks)
(1 mark)
O
H
C
N
b.
CH3
HKAL 1994 II Q7
NH2
CH3CH2COCl
(1 mark)
N
29
(i)
(ii)
Give one struccture for E annd one for F.. Draw a suittable represenntation for thhe chiral product.
(iii)
30
(i)
(ii)
Suggest the amount of acid required for the hydrolysis of 1 mole of the ester.
Explain
your answer.
(2 marks)
a.
b. (i)
(ii)
31
32
33
(ii)
L, C5H12O, can exist as a pair of enantiomers, and reacts with phosphorus pentachloride to give
hydrogen chloride.
(2 marks)
(i)
(ii)
34
COCl
HO(CH2)4OH
butane-1,4-diol
COCl
benzene-1,3-dicarbonyl chloride
(i)
(ii)
(iii)
35
36
(i)
Suggest tw
wo types of material
m
which can be maade from pollyesters.
37
Draw the structure, showing two repeating units, for each of the following polymeric materials:
(I)
poly(chloroethene) and
(II)
cellulose
(ii) Large quantities of poly(chloroethene) and cellulose used in daily life, Suggest, with explanation, an
appropriate waste disposal method for each material.
(5 marks)
38
(ii)
(iii)
(i)
(ii)
(iii)
39
c.
Dodecyl glucoside
g
is a new deterggent.
(i)
d
glucooside can be used in the cleansing
c
off oily dirts.
Exxplain why dedocyl
(ii)
40
(i)
n atom withh an
Coopy the structure of aspartame into your answerr book, and mark each cchiral carbon
assterisk.
(ii)
(iii)
41
salicin
Salicin undergoes acid hydrolysis to give glucose and 2-hydroxybenzyl alcohol.
#(i)
2-Hydroxybenzyl alcohol can be converted in two steps to acetylsalicylic acid, which is the active
ingredient of aspirin.
2-hydroxybenzyl alcohol
acetylsalicylic acid
(I)
(II)
42
51.
The fllow
diagram below
b
shows a route for the
t synthesis of PET.
(i)
(ii)) Polyethenne naphthalatte (PEN) is a polymer forrmed from naaphthalic aciid and ethanee-1,2-diol.
(I)
o PEN.
Drraw the struccture of a reppeating unit of
(II)
W
Which
polymeer, PET or PE
EN, do you expect
e
to be more rigid?
Explain.
(6 marrks)
43
Suggest a synthetic route with no more than three steps to convert benzene-1,4-dicarbaldehyde
to PET. (You are NOT allowed to use organic reagents with more than three carbon atoms.)
(ii)
Suggest why PET as compared with polystyrene, is more readily degraded in the environment.
(4 marks)
44
M
Miscellaneo
ous
53. HKAL 20000 II Q6e
Identify L,
L M and N inn the followiing reactionss:
45
benzoic acid
dichlorodifluoromethane
ethanoic acid
hexane
polystyrene
propanone
tetrachloromethane
triethylamine
For each of the descriptions of physical properties from (a) to (h) below, choose from the above list, one
substance which best fits the description.
(i)
46
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