COMPOUNDS CONTAINING OXYGEN

Fill in the blanks

1. Formic acid when heated with conc. H2SO4 produces.. (1983-1 Mark)

2. Ethanol vapour is passed over heated copper and the product is treated with aqueous
NaOH. The final product is. (1983-1 Mark)

3. The acidity of phenol is due to the.. of its anion (1984-1 Mark)

4. Formation of phenol from chlorobenzene is an example of aromatic

substitution. (1989-1 Mark)

5. Phenol is acidic because of resonance stabilization of its conjugate base, namely ..

(1990-1 Mark)

6. Fehlings solution A consists of an aqueous solution of copper sulphate, while Fehlings

solution B consists of an alkaline solution of. (1990-1 Mark)

7. The structure of the intermediate product formed by the oxidation of toluene with CrO 3 and
acetic anhydride, whose hydrolysis gives Benzaldehyde is..
(1992-1 Mark)

8. Aliphatic ethers are purified by shaking with a solution of ferrous salt to remove
which are formed on prolonged standing in contact with air.
(1992-1 Mark)

9. The structure of the enol form of CH 3 CO CH2 CO CH3 with intermolecular hydrogen
bonding is (1993-1 Mark)

10. Glycerine contains one. hydroxyl group. (1997-1 Mark)

True/False

1. Benzaldehyde undergoes aldol condensation in an alkaline medium. (1982-1 Mark)

2. Hydrolysis of an ester in presence of a dilute acid is known as saponification.(1983-1 Mark)

3. The yield of ketone when a secondary alcohol is oxidized is more than the yield of aldehyde
when a primary alcohol is oxidized. (1983-1 Mark)

4. Sodium ethoxide is prepared by the reaction of ethanol with aqueous sodium hydroxide.
(1986-1 Mark)

5. The reaction of methyl magnesium iodide with acetone followed by hydrolysis gives
secondary butanol. (1987-1 Mark)

6. The boiling point of propionic acid is less than that of n-butyl alcohol, an alcohol of
comparable molecular weight. (1991-1 Mark)

Multiple Choice Questions with ONE correct answer:

1. The compound which reacts fastest with Lucas reagent at room temperature is
(A) butan 1-ol (B) butan-2-ol
(C) 2-methylpropan-1-oI (D) 2-methylpropan-2-oI (1981-1 Mark)

2. The reagent with which both acetaldehyde and acetone react easily is
 Compounds Containing 2
Oxygen

(A) Fehlings reagent (B) Grignard reagent

(C) Schiffs reagent (D) Tollens reagent (1981-1 Mark)

3. A compound that gives a positive iodoform test is

(A) 1-pentanol (B) 2-pentanone
(C) 3-pentanone (D) pentanal (1982-1 Mark)

4. Diethyl ether on heating with conc. HI gives two moles of

(A) ethanol (B) iodoform
(C) ethyl iodide (D) methyl iodide (1983-1 Mark)

5. When acetaldehyde is heated with Fehlings solution it gives a precipitate of

(A) Cu (B) CuO
(C) Cu2O (D) Cu + Cu2O + CuO (1983-1 Mark)

6. The Cannizzaro reaction is not given by

(A) trimethylacetaldehyde (B) acetaldehyde
(C) benzaldehyde (D) formaldehyde (1983-1 Mark)

7 An industrial method of preparation of methanol is

(A) catalytic reduction of carbon monoxide in presence of ZnO Cr2O3
(B) by reacting methane with steam at 900C with a nickel catalyst
(C) by reducing formaldehyde with lithium aluminium hydride
(D) by reacting formaldehyde with aqueous sodium hydroxide solution (1984-1 Mark)

8 When phenol is treated with excess bromine water it gives

(A) m-Bromophenol (B) o- and p-Bromophenol
(C) 2, 4-Dibromophenol (D) 2, 4, 6-Tribromophenol (1984-1 Mark)

9. The compound that will not give iodoform on treatment with alkali and iodine is:
(A) acetone (B) ethanol
(C) diethyl ketone (D) isopropyl alcohol (1985-1 Mark)

10. HBr reacts fastest with

(A) 2-methylpropan-2-ol (B) propan-1-ol
(C) propan-2-ol (D) 2-methylpropan-1-ol (1986-1 Mark)

11 Which of the following compounds is oxidised to prepare methyl ethyl ketone?

(A) 2-Propanol (B) l-Butanol
(C) 2-Butanol (D) t-Butyl alcohol (1987-1 Mark)

12. Polarisation of electrons in acrolein may be written as

(A) C H 2 CH C O (B) C H 2 CH C O

(C) C H 2 C H CHO (D) C H 2 CH CH O (1988-1 Mark)

13 Phenol reacts with bromine in carbon disulphide at low temperature to give

(A) m-bromophenol (B) o- and p-bromophenol
(C) p-bromophenol (D) 2, 4, 6 tribromophenol (1988-1 Mark)

14. Read the following statement and explanation and answer as per the options given below:
Statement (S): Solubility of n-alcohols in water decreases with increase in molecular weight.
Explanation (E): The relative proportion of the hydrocarbon part in alcohols increases with
increasing molecular weight which permits enhanced hydrogen bonding with water
(A) Both (S) and (E) are correct and (E) is the correct explanation of (S).
 Compounds Containing 3
Oxygen

(B) Both (S) and (E) are correct but (E) is not the correct explanation of (S).
(C) (S) is correct but (E) is wrong.
(D) (S) is wrong but (E) is correct. (1988-2 Marks)

15. Chlorination of toluene in the presence of light and heat followed by treatment with aqueous
NaOH gives
(A) o-Cresol (B) p-Cresol
(C) 2, 4-Dihydroxytoluene (D) Benzoic acid (1990-1 Mark)

16. The enolic form of acetone contains

(A) 9 sigma bonds, 1 pi-bond and 2 lone pairs
(B) 8 sigma bonds, 2 pi-bonds and 2 lone pairs
(C) 10 sigma bonds, 1 pi-bond and 1 lone pair
(D) 9 sigma bonds, 2 pi-bonds and 1 lone pair (1990-1 Mark)

17. m-Chlorobenzaldehyde on reaction with conc. KOH at room temperature gives

(A) potassium m-chlorobenzoate and m-hydroxy benzaldehyde
(B) m-hydroxy benzaldehyde and m-chlorobenzyl alcohol
(C) m-chlorobenzyl alcohol and m-hydroxybenzyl alcohol
(D) potassium m-chlorobenzoate and m-chlorobenzyl alcohol. (1991-1 Mark)

18. Hydrogenation of benzoyl chloride in the presence of Pd on BaSO4 gives

(A) Benzyl alcohol (B) Benzaldehyde
(C) Benzoic acid (D) Phenol (1992-1 Mark)

19. Read the following statement and explanation and answer as per the options given below:
Statement: Acetate ion is more basic than the methoxide ion.
Explanation: The acetate ion is resonance stabilized
(A) Both S and E are true and E is the correct explanation of S.
(B) Both S and E are true but E is not the correct explanation of S.
(C) S is true but E is false.
(D) S is false but E is true (1994-2 Marks)

i LiAlH 4
20. The organic product formed in the reaction C6 H 5COOH ii H3O
(A) C6H5CH2OH (B) C6H5COOH & CH4
(C) C6H5CH3 & CH3OH (D) C6H5COOH & CH4 (1995-Scr.)

21. The reaction products of C6H5OCH3+HI .. is:
(A) C6H5OH + CH3I (B) C6H5I + CH3OH
(C) C6H5CH3 + HOI (D) C6H6 + CH3OH (1995-Scr.)

22. When phenol is reacted with CHCI3 and NaOH followed by acidification, salicyladehyde is
obtained. Which of the following species are involved in the above mentioned reaction as
intermediates?
(A) O (B) OH
H
CHCl 2
CCl 2

O
(C) (D) O
H Cl
CHCl 2

OH

(1995-Scr.)
 Compounds Containing 4
Oxygen

23. In the Cannizaros reaction given below,

2PhCHO OH PhCH 2 OH PhCO 2 , the slowest step is
(A) the attack of OH at the carbonyl group,
(B) the transfer of hydride to the carbonyl group,
(C) the abstraction of proton from the carboxylic acid,
(D) the deprotonation of PhCH2OH (1996-1 Mark)

24. The order of reactivity of the following alcohols towards conc. HCI is
CH3
H3C CH3
F CH3

F OH OH OH Ph OH
I II III IV
(A) I > II > III > IV (B) I > III > II > IV
(C) IV > III > II > I (D) IV > III > I > II (1992-1 Mark)

25. The correct statement about the compounds A, B and C is

(A) A and B are identical (B) A and B are diastereomers
(C) A and C are enantiomers (D) A and B are enantiomers(1997-1 Mark)
COOCH 3 COOH COOH

H OH H OH H OH

H OH H OH HO H

COOH COOCH 3 COOCH 3

(A) (B) (C)

26. In a Cannizzaros reaction, the intermediate that will be the best hydride donor is
(A) H (B) H

O O
OH O

(C) H (D) H

O O
O O
OMe
O 2N (1997-1 Mark)
27. Read the following statement and explanation and answer as per the options given below:
Assertion: Acetic acid does not undergo haloform reaction.
Reason: Acetic acid has no alpha hydrogens.
(A) If both assertion and reason are correct, and reason is the correct explanation of
assertion.
(B) If both assertion and reason are correct, but reason is not the correct explanation 9 the
assertion.
(C) If assertion is correct but reason is incorrect.
(D) If assertion is incorrect but reason. is correct. (1998-2 Marks)
28. When propionic acid is treated with aqueous sodium bicarbonate, CO2 is liberated. The C
of CO2 comes from
(A) methyl group (B) carboxylic acid group
(C) methylene group (D)-bicarbonate (1999-2 Marks)
 Compounds Containing 5
Oxygen

29. The enol form of acetone, after treatment with D2O gives.
(A) OD (B) O

H3C C CH2 D3 C C CD3

(C) OH (D) OD

H2C C CH2D D2 C C CD3 (1999-2 Marks)

30. Which one of the following will most readily be dehydrated in acidic condition?
(A) OH O (B) OH

(C) O (D) O

OH OH (2000-Scr.)

31. Benzoyl chloride is prepared from benzoic acid by

(A) Cl2,h (B) SO2Cl2
(C) SOCl2 (D) Cl2, H2O (2000-Scr.)

32. The appropriate reagent for the following transformation is

O

CH2CH3
CH3

HO HO
(A) Zn(Hg), HCl (B) NH2NH2, OH
(C) H2/Ni (D) NaBH4 (2000-Scr.)

33. The compound that will react most readily with NaOH to form methanol is
(A) (CH3)4N+I (B) CH3OCH3
+
(C) (CH3)3S I (D) (CH3)3CCl (2001-Scr.)

34. Read the following statement and explanation and answer as per the options given
below:
Assertion: Dimethylsulphide is commonly used for the reduction of an ozonide of an
alkene to get the carbonyl compounds.
Reason: It reduces the ozonide giving water soluble dimethyl sulphoxide and excess of it
evaporates.
(A) If both assertion and reason are CORRECT, and reason is the CORRECT explanation of
the assertion.
(B) If both assertion and reason are CORRECT, but reason is NOT the CORRECT
explanation of the assertion.
(C) If assertion is CORRECT, but reason is INCORRECT.
(D) If assertion is INCORRECT, but reason is CORRECT. (2001-Scr.)

35. A mixture of benzaldehyde and formaldehyde on heating with aqueous NaOH solution gives
(A) benzyl alcohol and sodium formate (B) sodium benzoate and methyl alcohol
(C) sodium benzoate and sodium formate (D) benzyl alcohol and methyl alcohol
(2001-Scr.)
 Compounds Containing 6
Oxygen

36. 1-propanol and 2-propanol can be best distinguished by (2001-Scr.)

(A) oxidation with alkaline KMnO4 followed by reaction with Fehling solution
(B) oxidation with acidic dichromate followed by reaction with Fehling solution
(C) oxidation by heating with copper followed by reaction with Fehling solution
(D) oxidation with concentrated H2SO4 followed by reaction with Fehling solution

37. The product of acid hydrolysis of P and Q can be distinguished by

CH3COO H3C
P = H2C Q=
CH3 CH3COO
(A) Lucas Reagent (B) 2, 4-DNP
(C) Fehlings Solution (D) NaHSO3 (2003-Scr.)

38. OH

C 2 H 5
I OC2 H5
Anhydrous C2 H 5OH
?

(A) C6H5OC2H5 (B) C2H5OC2H5

(C) C6H5OC6H5 (D) C6H5I (2003-Scr.)

39. CHO OHC

i NaOH /100 C
(ii)H / H 2 O
Major product is

CHO OHC
(A) COOH HOOC (B) OH HOOC

COOH HOOC COOH HO

(C) O (D) CH2OH HOH2C
O

CH2OH HOH2C

O (2003-Scr.)
O

40. Ethyl ester CH3 MgBr

excess
P. The product P will be
 Compounds Containing 7
Oxygen
(B) H3C C2 H5
(A) H3C CH3

H5 C 2 OH
H3C OH
(C) H5 C2 C2 H5 (D) H5 C2 C2 H5

H5 C 2 OH H3C OH (2003-Scr.)

41. An enantiomerically pure acid is treated with racemic mixture of an alcohol having one chiral
carbon. The ester formed will be
(A) Optically active mixture (B) Pure enantiomer
(C) Meso compound (D) Racemic mixture (2003-Scr.)

42. The correct order of reactivity of PhMgBr with

O O O

Ph C Ph H3C C H H3C C CH3 is

(I) (II) (III)
(A) (I) > (II) > (Ill) (B) (Ill)> (II)> (I)
(C) (II) > (III) > (I) (D) (I) > (Ill) > (II) (2004-Scr.)

43. The product of acid catalyzed hydration of 2-phenylpropene is

(A) 3-phenyl-2-propanol (B) 1-phenyl-2-propanol
(C) 2-phenyl-2-propanol (D) 2-phenyl-1-propanol (2004-Scr.)

44. The best method to prepare cyclohexene from cyclohexanol is by using

(A) Conc. HCI + ZnCI2 (B) Conc. H3PO4
(C) HBr (D) Conc. HCI (2005-Scr.)

45. How will you Convert butan2one to propanoic acid?

(A) Tollens reagent (B) Fehlings solution
+
(C) NaOH/I2/H (D) NaOH/NaI/H+ (2005-Scr.)

46.
CHO X
CH 3 COONa
OMe H 3O
CH CHCOOH

The compound (X) is

(A) CH3COOH (B) BrCH2 COOH
(C) (CH3CO)2O (D) CHO COOH (2005-Scr.)

47. 4-methyl benzensuphonic acid reacts with sodium acetate to give

(A) CH3 (B) COONa

; CH3COOH ; SO 3

SO 3Na CH3
 Compounds Containing 8
Oxygen
(D) O 2S O COCH3
(C)
; SO 3
; NaOH

CH3
CH3 (2005-Scr.)

Multiple Choice Questions with ONE MORE THAN ONE correct answer:

1. Base catalysed aldol condensation occurs with:

(A) propionaldehyde (B) benzaldehyde
(C) 2-Methly propionaldehyde (D) 2, 2-Dimethyl propionaldehyde
(1984-1 Mark)

2. Which of the following compounds will give a yellow precipitate with iodine and alkali?
(A) 2-Hydroxy propane (B) acetophenone
(C) methyl acetate (D) acetamide (1984-1 Mark)

3. Which of the following compounds will react with ethanolic KCN?

(A) ethyl chloride (B) acetyl chloride
(C) chlorobenzene (D) benzaldehyde (1984-1 Mark)

4. Keton-enol tautoomeism is observed in

(A) O (B) O

H5 C 6 C H C
H5 C6 CH3
(C) O (D) O

H5 C 6 C C6 H5
H5 C6 CH3 (1988-1 Mark)
5. Which of the following are the examples of aldol condensation?
(A) 2CH 3CHO
dil. NaOH
CH 3CHOHCH 2 CHO
(B) 2CH 3COCH 3
dil. NaOH
CH 3COHCH 3CH 2 COCH 3
(C) 2HCHO
dil. NaOH
CH 3OH
(D) C6 H5 CHO HCHO
dil. NaOH
C6 H 5CH 2 OH (1989-1 Mark)

6. Which of the following will give yellow precipitate with I2/NaOH?

(A) ICH2COCH2CH3 (B) CH3COOCOCH3
(C) CH3CONH2 (D) CH3CH(OH)CH2CH3 (1997-2 Marks)

7. H 3C
The reaction of CH OH with HBr gives
 Compounds Containing 9
Oxygen
(B) H 3C
(A) Br
OH
H 3C
Br
OH

(C) Br (D) H 3C
H 3C Br
Br Br
(1998-2 Marks)

8. A new carbon-carbon bond formation is possible in

(A) Cannizzaro reaction (B) Friedel-Crafts alkylation
(C) Clemmensen reduction (D) Remier-Tiemann reaction (1998-2 Marks)
9. Which of the following will react with water?
(A) CHCI3 (B) CI3CCHO
(C) CCI4 (D) ClCH2CH2Cl (1998-2 Marks)

10. Which of the following will undergo aldol condensation?

(A) acetaldehyde (B) propanaldehyde.
(C) benzaldehyde (D) trideuteroacetaldehyde (1998-2 Marks)

11.
O
The ether when treated with HI produces

(A) (B)
CH2I CH2OH

(C) (D)
I OH
(1999-3 Marks)

Subjective Problems: Students are advised to attempt the questions, marked with in second
round

1. A compound (X) containing C, H and O is unreactive towards sodium. It does not add
bromine. It also does not react with Schiffs reagent. On refluxing with an excess of
hydroiodic acid, (X) yields only one organic product (Y). On hydrolysis, (Y) yields a new
compound (Z) which can be converted into (Y) by reaction with red phosphorus and iodine.
The compound (Z) on oxidation with potassium permanganate gives a carboxylic acid. The
equivalent weight of this acid is 60. What are the compounds (X). (Y) and (Z). Write chemical
equations leading to the conversion of(X) to (Y). (1981-3 Marks)

2. Write the structural formula of the main organic product formed when:
(i) methanal reacts with ammonia (1981-1/2 Mark)
(ii) ethyl acetate is treated with double the molar quantity of ethyl magnesium bromide and
the reaction mixture poured is into water. (1981-1/2 Mark)
CH 3CH 2COCl / AlCl 3
(iii) benzene
(1985-1 Mark)
NaOH

(iv) propanal heat (1985-1 Mark)
Compounds Containing 10
Oxygen

I2

(v) ethanol NaOH (1985-1 Mark)
(vi)
K OH
H3OC CHO HCHO

(1992-1 Mark)
(vii) C6H 5COOH CH 3MgI ? ? (1993-1 Mark)
1.CH 3MgBr excess
(viii) C6H 5CH 2CO2CH
3 2. H (1994-1 Mark)
A B
P and 1. alcoholic K OH excess
(ix) CH 3 CH 2 COOH
bromin
................. .................
e 2. H

(1995-2 Marks)
D
NaOC H in absolute
(x) C6H 5 CHO CH 3 COO2H 5
C H2OH5 and heat ................. (1995-1 Mark)
2 5
G H I
SOCl 2 anhydrous Zn Hg
(xi) o HOOC C 6H 4 CH 2 C 6H
5
.................
AlCl 3
.................H HCl
.................
(1995-2 Marks)
(xii) Predict the structure of the product in the following reaction. (1996-1 Mark)
Br

H Ph
NaI
acetone
C
MeO H

Ph

(xiii) Complete the following reaction with appropriate structure. (1996-1 Mark)

H3CH2C
1. K CN / H 2SO4

O 2. L iAlH 4
(D)
H
(xiv)
E
Ph3P CH 2
..............

O (1997-1 Mark)
F
(xv) COOH CH 2OH conc. H 2SO4 ................. (1997-1 Mark)
2 2
(xvi) G
R C C R HClO4
..............

C
R n Pr
O (1997-1 Mark)
I
(xvii) ClCH 2CH 2CH 2COPh K OH MeOH ................. (1997-1 Mark)
J
(xviii) H 3CCOCOC6H 5 NaOH / H 3O
................. (1997-1 Mark)
HI excess Heat
(xix) CH 3 2 CHOCH 3
2 products (1998-2 Marks)
(xx) Ph
base


O

Br (2000-1 Mark)
(xxi) Write the structures of the products A and B.
 Compounds Containing 11
Oxygen

O
18 H 3O
H3C C OC2H
5 A B
(2000-2 Marks)
(xxii) Identify A, B and C are give their structures. (2000-3 Marks)
O

CH 3
Br2
NaOH
A B
CH 3
H
C7H12O

O

3. Write the chemical equation to show what happens when ethyl acetate is treated with
sodium ethoxide in ethanol and the reaction mixture is acidified. (1981-2 Marks)
4. (i) Outline the reaction sequence for the conversion of methanal to ethanal (the number of
steps should not be more than three). (1981-2 Marks)
(ii) 1-propanol from 2-propanol (in three steps) (1982-1 Mark)
(iii) acetylene to acetone. (1985-1 Mark)
(iv) ethyl alcohol to vinyl acetate (in not more than 6 steps) (1986-3 Mark)
(v) phenol to acetophenone. (1989-1.5 Mark)
(vi) acetic acid to tertiary butyl alcohol (1989-1.5 Mark)
(vii)Ethanal to 2-hydroxy-3-butenoic acid. (1990-2 Marks)
(viii) Ethanoic acid to mixture of methanoic acid and diphenyl ketone. (1990-2 Marks)
(ix) Carry out the following transformation in not more than three steps
O

C C H
H3C CH3
H3C (1999-3 Marks)
(x) OH

Asprin

(2003-2 Marks)

5. Outline the accepted mechanism of the following reaction. Show the various steps including
the charged intermediates.
CH3
O
C
O
AlCl 3
HCl
H3C Cl
(1981-3 Marks)

6. State with balanced equations what happens when:

(i) acetic anhydride reacts with phenol in presence of a base. (1982-1 Mark)
(ii) Ethylene glycol is obtained by the reaction of ethylene with potassium permanganate.
(1991-1 Mark)

7. An alkene (A) on ozonolysis yields acetone and an aldehyde. The aldehyde is easily
oxidized to an acid (B). When .B is treated with bromine in presence of phosphorus, it yields
a compound (C) which on hydrolysis gives a hydroxy acid (D). This acid can also be
obtained from acetone by the reaction with hydrogencyanide followed by hydrolysis. Identify
the compounds A, B, C and D. (1982-2 Marks)

8. Give reasons for the following:

 Compounds Containing 12
Oxygen

(i) Sodium metal can be used for drying diethyl ether but not ethanol. (1982-1 Mark)
(ii) Acetic acid can be halogenated in the presence of red P and Cl 2 but formic acid cannot
be halogenated in the same way. (1983-1 Mark)
(iii) Formic acid is a stronger acid than acetic acid; (1985-1 Mark)
(iv) Suggest a reason for the large difference between the boiling points of butanol and
butanal, although they have almost the same solubility in water. (1985-2 Mark)
(v) Hydrazones of aldehydes and ketones are not prepared in highly acidic medium.
(1986-1 Mark)
(vi) Phenol is an acid but it does not react with NaHCO3 (1987-1 Mark)
(vii)Iodoform is obtained by the reaction of acetone with hypoiodite but not with iodide
(1991-1 Mark)
+ +
(viii) In acylium ion, the structure R CO is more stable than R C =O(1994-1 Mark)
(ix) Although phenoxide ion has more number of resonating structures than benzoate ion,
benzoic acid is stronger acid than phenol. Why? (1997-2 Mark)
(x) Acid catalyzed dehydration of t-butanol is faster than that of n-butanol.(1998-2 Marks)
(xi) Explain why o-hyroxybenzaldehyde is a liquid at room temperature while
p-hydroxybenzaldehyde is a high melting solid. (1999-2 Marks)

9. State the conditions under which the following preparation are carried out. Give the
necessary equations which need not be balanced. (1983-1 Mark each)
(i) Ethanol from acetylene
(ii) Acetic acid from methyl iodide

10. An alcohol A, when heated with conc. H2SO4 gives an alkene B. When B is bubbled through
bromine water and the product obtained is dehydro-halogenated with excess of sodamide, a
new compound C is obtained. The compound C gives D when treated with warm dilute
H2SO4 in presence of HgSO4. D can also be obtained either by oxidizing A with KMnO 4 or
from acetic acid through its calcium salt. Identify A, B, C and D. (1983-4 Marks)

11. What happens when p-xylene is reacted with concentrated sulphuric acid and the resultant
product is fused with KOH? (1984-2 Marks)

12. Write down the reactions involved in the preparation of the following using the reagents
indicated against it in parenthesis:
Propionic anhydride from propionaldehyde AgNO3 /NH 4OH,P2O5
(1984-2 Marks)

13. A compound of molecular formula C7H8O is insoluble in water and dilute sodium bicarbonate
but dissolves in dilute aqueous sodium hydroxide. On treatment with bromide water, it readily
gives precipitate of C7H8OBr3. Write down the structure of the compound.
(1985-2 Marks)

14. Give a chemical test/suggest a reagent to distinguish between the following pairs of
compounds
(i) methanol and ethanol. (1985-1 Mark)
(ii) acetaldehyde from acetone. (1987-1 Mark)

15. Arrange the following in increasing ease of hydrolysis

CH 3COOC2H 5 , CH 3COCl, CH 3CO 2 O, CH 3CONH 2 (1986-1 Mark)

16. A white precipitate was formed slowly when silver nitrate was added to a compound (A) with
molecular formula C6H13Cl. Compound (A) on treatment with hot alcoholic potassium
hydroxide gave a mixture of two isomeric alkenes (B) and (C), having formula C 6H12. The
mixture of (B) and (C), on ozonolysis, furnished four compounds:
 Compounds Containing 13
Oxygen
H3C CH CHO
(i) CH3CHO
(ii) C2H5CHO (iii) CH3COCH3 and (iv) CH3
What are the structures of (A), (B) and (C)? (1986-4 Marks)

17. A liquid (X), having a molecular formula C6H12O2 is hydrolysed with water in the presence of
acid to give a carboxylic acid (Y) and an alcohol (Z). Oxidation of (Z) with chromic acid gives
(Y). What are the structures of(X), (Y) and (Z)? (1986-3 Marks)

18. Complete the following with appropriate structures:

(i) CH 3CO 2 O C H OH
2 5 CH3COOH ? (1986-1 Mark)
(ii) OH OH

CHO

(1986-1 Mark)
(iii)
NaOH

? CH CH CHO

(1986-1 Mark)
(iv)
fu min g NaOH
SO3H ..............
.............
H 2SO4 fuse 2. H

(1992-1 Mark)
19. An unknown compound of carbon, hydrogen and oxygen contains 69.77% carbon and
11.63% hydrogen and has a molecular weight of 86. It does not reduce Fehling, solution, but
forms a disulphite addition compound and gives a positive iodoform test. What are the
possible structures? (1987-5 Marks)

20. An organic compound (A) on treatment with acetic acid in the presence of sulphuric acid
produces an ester (B), (A) on mild oxidation gives (C), (C) with 50% potassium hydroxide
followed by acidification with dilute hydrochloric acid generates (A) and (D), (D) with
phosphorus penta chloride followed by reaction with ammonia gives (E), (E) on dehydration
produces hydrocyanic acid. Identify the compounds A, B, C, D and E. (1987-5 Mark)

21. Complete the following reactions:

(i) OH
CH3MgBr ?
H 3C CHO

? H3C C CH3

OH (1988-1 Mark)
(ii) CH 3COOH
?

ClCH 2COOH
excessNH 3
? (1988-1 Mark)
(iii) O
base catalyst acid catalyst
2CH2CCH3
? ?
(1988-1 Mark)
(iv) SO3H OH

CHCl 3 / NaOH

?
?
?

(1988-1 Mark)

22. A hydrocarbon A (molecular formula C5H10) yields 2-methyl butane on catalytic

hydrogenation. A adds HBr (in accordance with Markownikoffs rule) to form a compound
 Compounds Containing 14
Oxygen

B which on reaction with silver hydroxide forms an alcohol C (C 5H12O), C Alcohol C on

oxidation gives a ketone D. Deduce the structures of A, B, C and D and show the reactions
involved. (1988-5 Marks)

23. A ketone A which undergoes haloform reaction gives compound B on reduction. B on

heating with sulphuric acid gives compound C, which forms mono ozonide D. D on
hydrolysis in presence of zinc dust gives only acetaldehyde. Identify A, B and C. Write down
the reactions involved. (1989-4 Marks)

24. The sodium salt of a carboxylic acid, A, was produced by passing a gas, B, into an aqueous
solution of caustic alkali at an elevated temperature and pressure. A, on heating E in
presence of sodium hydroxide followed by treatment with sulphuric acid gave a dibasic acid,
C. A sample of 0.4 g of acid C, on combustion gave 0.08 g of water and 0.39 g of carbon
dioxide. The silver salt the acid weighing 1.0 g on ignition yielded 0.71 g of silver as residue.
Identify A, B and C. (1990-5Marks)

25. Compound A (C6H12O2) on reduction with LiAIH4 yielded to compounds B and C. The
compound B on oxidation gave D, which on treatment with aqueous alkali and subsequent
heating furnished E. The later on catalytic hydrogenation gave C. The compound D was
oxidized further to give F which was found to be a monobasic acid (molecular formula
weight 60.0). Deduce the structure of A, B, C, D and E. (1990-4 Marks)

26. An organic compound containing C, H and O exists in two isomeric forms A and B. An
amount of 0.108 g of one of the isomers gives on combustion 0.308 g of CO 2 in 0.072 g of
H2O. A is insoluble in NaOH and NaHCO 3 while B is soluble in NaOH. A reacts with conc. HI
to give compounds and D. C can be separated from D by the ethanolic AgNO 3 solution and
D is soluble in NaOH. B reacts readily with bromine water to give compound E of molecular
formula, C7H5OBr3 Identify A, B, C, D and E with justification and give their structures.
(1991-6 Marks)

PCl NH 3 P2O5 H 2 / Ni
27. (i) C6H 5COOH

5
C D C 6H 5CN E: (1991-2 Marks)
Identify C, D and E.
NaBH 4 HCl K CN
(ii) H 3C CH CH CHO
F ZnCl 2
G
H
H:
Identify F, G and H. (1991-2 Marks)

28. Compound X, containing chlorine on treatment with strong ammonia gives a solid Y which
is free from chlorine. Y analyzed as C = 49.31%, H = 9.59% and N = 19.18% and reacts
with B2 caustic soda to give a basic compound Z. Z reacts with HNO 2 to give ethanol.
Suggest structures for X, Y and Z. (1992-1 Mark)

29. An organic compound A on treatment with ethyl alcohol gives a carboxylic acid B and
compound C. Hydrolysis of C under acidic conditions gives B and D. Oxidation of D with
KMnO4 also gives B. B on heating with Ca(OH) 2 gives E (molecular formula C3H6O).E
does not give Tollens test and does not reduce Fehlings solution but forms a
2, 4-dinitrophenyl hydrazone Identify A, B, C, D and E. (1992-3 Marks)

30. Compound X (molecular formula, C5H8O) does not react appreciably with Lucas reagent at
room temperature but gives a precipitate with ammonical silver nitrate. With excess of
MeMgBr, 0.42 g of X gives 224 ml of CH4 at STP. Treatment of X with H2 in presence of Pt
catalyst followed by boiling with excess HI, gives n-pentane. Suggest structure for X and
write equation involved. (1992-5 Marks)

31. Arrange the following in increasing order of expected enol content.

CH 3COCH 2CHO CH 3COCH 3 CH 3CHO CH 3COCH 2COCH 3 (1992-1 Mark)
 Compounds Containing 15
Oxygen

32. Identify C(C4H8) which when treated with. H2O / H2SO4 gives C4H10O which cannot be
resolved into optical isomers. (1993-1 Mark)

33. In the following reactions identify the compounds A, B, C and D.

PCl 5 SO2 A B
A CH 3COOH C SO
2 HCl
2C CH 3 2 Cd 2D CdCl 2 (1994-4 Marks)

34. When gas A is passed through dry KOH at low temperature, a deep red coloured compound
B and a gas C are obtained. The gas A, on reaction with but-2-ene, followed by treatment
with Zn/H2 yields acetaldehyde. Identify A, B nd C. (1994-3 Marks)

35. When t-butanol and n-butanol are separately treated with a few drops of dilute KMnO 4, in
one case only the purple colour disappears and a brown precipitate is formed. Which of the
two alcohols gives the above reaction and what is the brown precipitate? (1994-2 Marks)

36. An organic compound A, C8H6, on treatment with dilute sulphuric acid containing mercuric
sulphate gives a compound B, which can also be obtained from a reaction of benzene with
an acid chloride in the presence of anhydrous aluminium chloride. The compound B, when
treated with iodine in aqueous KOH, yields C and a yellow compound D. Identify A, B, C and
D with justification. Show how B is formed from A. (1994-3 Marks)

37. When phenol is reacted with CHCI 3 and NaOH followed by acidification, Salicylaldehyde is
obtained. Which of the following species are involved in the above mentioned reaction as
intermediates? (1995-2 Marks)
O OH O O

H CHCl 2 H CHCl 2

(i) CCl2 (ii) (iii) CHCl (iv)

OH

38. Which of the following carboxylic acids undergoes decarboxylation easily? Explain briefly.

(i) C6H5 CO CH2 COOH (ii) C6H5 CO COOH

(iii) H5 C6 CH COOH (iv) H5 C6 CH COOH

OH NH2 (1995-2 Marks)

39. 3, 3-Dimethylbutan-2-ol loses a molecule of water in the presence of concentrated sulphuric

acid to give tetramethylethylene as a major product. Suggest a suitable mechanism.
(1996-2 Marks)

40. A compound D (C8H10O) upon treatment with alkaline solution of iodine gives a yellow
precipitate. The filtrate on acidification gives a white solid E (C 7H6O2). Write the structures of
D, E and explain the formation of E. (1996-2 Marks)

41. An optically active alcohol A (C6H10O) absorbs two moles of hydrogen per mole of A upon
catalytic hydrogenation and gives a product B. The compound B is resistant to oxidation by
CrO3 and does not show any optical activity. Deduce the structures of A and B.
(1996-2 Marks)

42. Predict the structures of the intermediates/products in the following reaction sequence:
 Compounds Containing 16
Oxygen

OMe O O

OMe
1. AlCl Zn Hg / HCl H 3PO4
O
3 A B
2. H 3O

O (1996-2Marks)

43 Suggest appropriate structures for the missing compounds

(The number of carbon atoms remains the same throughout the reactions.)
CH3

OH
dil.
K MnO

4 A HI O4
B C

CH3 (1996-3 Marks)

44. A hydrocarbon A of the formula C7H12 on ozonolysis gives a compound B which undergoes
condensation giving 1-acetylcyclopentene. Identify A and B. (1997-2 Marks)

45. How many asymmetric carbon atoms are created during the complete reduction of benzyl
(PhCOCOPh) with LiAIH4? Also write the number of possible stereo-isomers in the product.
(1997-2 Marks)

46. A liquid A is reacted with hot aqueous sodium carbonate solution. A mixture of two salts B
and C are produced in the solution. The mixture on acidification with sulphuric acid and
distillation produces the liquid A again. Identify A, B and C and write the equations involved.
(1997-3 Marks)

47. Predict the major product in each of the following reactions. (1997-1 Mark each)
(i) O

CH3 1.Br2 1 equivalent

2. NaBH4

3. Base

(ii) O

1. MeMgBr
2.aq. HCl

48. (i) Write down the structures of E and F. (1997-2 Mark each)
OH
E C11H14O2
F CH 3CH 2COO

COOH

1. K MnO4 / OH

F
2. H

COOH
(ii) Write down the structures of G and H where G is C4H8O3.
 Compounds Containing 17
Oxygen

Ac O NaHCO3
Acetate
pyridine
2 G CO2

CrO3
H
Warm

CH 3COCH 3 CO2

49. 2, 2-Dimethyloxirane can be cleaved by acid (H+) Write mechanism. (1996-2 Marks)

50. Which of the following is the correct method for synthesising methyl-t-butyl ether and why?
(i) CH 3 3 CBr NaOMe (ii) CH 3Br NaO t Bu
(1997-2 Marks)

51. An ester A (C4H8O2), on treatment with excess methyl chloride followed by acidification, gives
an alcohol B as the sole organic product. Alcohol B, on oxidation with NaOCI followed by
acidification, gives acetic acid. Deduce the structures of A and B. Show the reactions
involved. (1998-6 Marks)

52. An aldehyde A(C11H8O2), which does not undergo self aldol condensation, gives
benzaldehyde and two moles of B on ozonolysis. Compound B, on oxidation with silver ion
gives oxalic acid. Identify the compounds A and B. (1998-2 Marks)

53. Write the intermediate steps each of the following reactions.

H 3O
(i) C6H 5CH OH C CH
6H 5CH
C CHCHO (1998-2 Marks)
(ii)
H

OH CH3
O (1998-1 Mark)

54. Complete the following reaction with appropriate structures of products/reagents

O

O CHC6H5
i L iAlH 4

C
ii H , Heat
D
(1998-4
Marks)

55. Complete the following reaction with appropriate reagents:

D D HO CH3
4 5 6
C C


D C C H
H3C H H3C C D
CH3 CH3
CH3 CH3 (1999-3 Marks)

56. Explain briefly the formation of the products giving the structures of the intermediates.
CH CH CH2 H2 C
CH2 HCl
H2C CH2 OH H2C CH2
Cl
CH CH2Cl etc.
H2 C
CH3 CH3

CH CH CH CH (only)
HCl
H2C CH2 OH H2C CH2 Cl
(1999-3 Marks)
 Compounds Containing 18
Oxygen

57. Explain briefly the formation of the products giving the structures of the intermediates.
O O

H3C C OC2H5
C OC2H5 CH O

NaOEt i OH
H2C Br
H3C CH C OH
ii 2H
C OC2H5 H 2C C OH
O O (1999-5 Marks)

58. An organic compound A, C6H10O on reaction with CH3MgBr followed by acid treatment gives
compound B. The compound B on ozonolysis gives compound C, which in presence of a
base gives 1-acetyl cyclopentene D. The compound B on reaction with HBr gives compound
E. Write the structures of A, B, C and E. Show how D is formed from C. (2000-5 Marks)

59. Write the structures of alanine at pH = 2 and pH = 10. (2000-2 Marks)

60. An organic compound A, C8H4O3 in dry benzene in. the presence of anhydrous AICl 3 gives
compound B. The compound B on treatment with PCI 5 followed by reaction with H2/Pd
(BaSO4) gives compound C, which on reaction with hydrazine gives a cyclised compound D
(C14H10N2) Identify A, B, C and D. Explain the formation of D from C. (2000-5 Marks)

61. Identify (A), (B), (C), (D) and (E) in the following schemes and write their structures:
NaOD / D2O excess
Br2 / CCl 4
A NaNH 2
B HgSO4 / H 2SO4
C NH 2NHCONH 2
D E

(2001-5 Marks)

62. Identify (X), (Y) and (Z) in the following synthetic scheme and write their structures. Explain
the formation of labelled formaldehyde (HCHO) as one of the products when compound (Z)
is treated with HBr and subsequently ozonolysed. Mark the C* carbon in the entire scheme.
BaC * O3 H 2SO4 X gas C * denotes C14

i Mg / ether ii X iii H 3O
CH 2 CH Br Y L iAlH 4
Z (2001-5 Marks)
63. Five isomeric para-disubstituted aromatic compounds A to E with molecular formula C 8H8O2
were given for identification. Based on the following observations, give structures of the
compounds. (2002-5 Marks)
(i) Both A and B form a silver mirror with Tollens reagent; also B gives a positive test with
FeCl3 solution.
(ii) C gives positive iodoform test.
(iii) D is readily extracted in aqueous NaHCO3 solution.
(iv) E on acid hydrolysis gives I, 4-dihydroxybenzene.

64. Identify X, Y and Z in the following synthetic scheme and write their structures.
2
i NaNH ii CH 3CH 2Br
CH 3CH 2C C H X H2PdBaSO4 Y AlkalineK MnO4 Z
Is the compound Z optically active? Justify your answer. (2002-5 Marks)

65. A biologically active compound, Bombykol (C16H30O) is obtained from a natural source. The
structure of the compound is determined by the following reactions. (2002-5 Marks)
(A) On hydrogenation, Bombykol gives a compound A, C 16H34O, which reacts with acetic
anhydride to give an ester;
(B) Bombykol also reacts with acetic anhydride to give another ester which on oxidative
ozonolysis (O3/H2O2) gives a mixture of butanoic acid, oxalic acid and 10-
acetoxydecanoic acid. Determine the number of double bonds in Bombykol. Write the
 Compounds Containing 19
Oxygen

structures of compound A Bombykol. How many geometrical isomers are possible for
Bombykol? (2002-5 Marks)

66. A racemic mixture of () 2-phenylpropanoic acid on esterification with (+) 2-butanol gives
esters. Mention the stereochemistry of the two esters produced. (2003-2 Marks)

67. Compound A of molecular formula C9H7O2Cl exists in ketoform and predominantly in enolic
form B. On oxidation with KMnO4, A gives m-chlorobenzoic acid Identify A and B.
(2003-2 Marks)

68. An organic compound (P) of molecular formula C5H10O is treated with dil. H2SO4 to give
compounds (Q) and (R) both of which responds iodoform test The rate of reaction of (P) with
dil. H2SO4 is 1010 faster than the reaction of ethylene with dil. H 2SO4. Identify the organic
compounds (P), (Q) and (R) and explain the extra reactivity of (P). (2004-4 Marks)

69. Identify (X) and (Y) in the following reaction sequence

O
HO
H3C C CH3

H

X O3
Zn CH 3COOH Y aq. NaOH

(2005-2 Marks)

70. A monomer of a polymer on ozonolysis gives two moles of CH 2O and one mole of
CH3COCHO. Write the structure of monomer and write all-cis configuration of polymer chain.
(2005-2 Marks)
 Compounds Containing 20
Oxygen

ANSWERS

A 1. CO 2. aldol (-hydroxybutanol) 3. resonance stabilization

4. nucleophilic 5. phenoxide ion 6. sodium potassium tartarate
7. C6H5CH(OCOCH3)2 8. peroxides
9. H3C C CH C CH3

O O
H
10. secondary

B 1. F 2. F 3. T 4. F 5. F 6. F

C 1. (d) 2. (b) 3. (b) 4. (c)

5. (c) 6. (b) 7. (a) 8. (d)
9. (c) 10. (a) 11. (c) 12. (d)
13. (b) 14. (c) 15. (d) 16. (a)
17. (d) 18. (b) 19. (d) 20. (a)
21. (a) 22. (d) 23. (b) 24. (c)
25. (d) 26. (d) 27. (c) 28. (d)
29. (b) 30. (a) 31. (c) 32. (b)

33. (a) 34. (a) 35. (a) 36. (c)

37. (c) 38. (b) 39. (b) 40. (a)

41. (a) 42. (c) 42. (c) 44. (b)

45. (c) 46. (c) 47. (a)

D 1. (a, c) 2. (a, b) 3. (a, b, d) 4. (b, d)

5. (a, b) 6. (d) 7. (b) 8. (b, d)
9. (b) 10. (a, b, d) 11. (a, d)

E 1. C2H5OC2H5, C2H5I, C2H5OH

7. (CH3)2CHCH = C(CH3)2, (CH3)2CHCOOH, (CH3)2C(Br)COOH, (CH3)2C(OH)COOH

10. CH3.CH2OH, CH2 = CH2, CH CH, CH3.CHO

13. m-cresol

15. CH3CONH2 < CH3COOC2H5 < (CH3CO)2O < CH3COCl

16. C2H5CH(Cl).CH(CH3)2, CH3CH = CH.CH(CH3)2, C2H5CH = C(CH3)2

Compounds Containing 21
Oxygen

17. H5 C2 C OC3H7 ; C2H5COOH, C3H7OH

O
19. C3H7COCH3 or (CH3)2CHCOCH3

20. CH3OH, CH3COOCH3, HCHO, HCOOH, HCONH2

O
22. (CH3)2CHCH = CH2, (CH3)2CHC(Br)CH3, (CH3)CHCH(OH)CH3, ||
(CH 3 )2 CH CCH 3

23. H3 C C C 2H 5 ; H 3C CH C2H5 ; HCH3C CH.CH3

O OH

24. HCOONa, CO2, (COOH)2

25. C3H7COOC2H5, C2H5OH, C4H9OH, CH3CHO

26. OCH3 OH OH OH
Br Br

, , CH3I , ,

CH3 CH3
(D)
Anisole (A) m-Cresol, (B) Br
(E) C7H5OBr3

28. C2H5COCl, C2H5CONH2, C2H5NH2

29. CH3CO.O.COCH3, CH3COOH, CH3COOC2H5, C2H5OH, CH3COCH3

30. HC C.CH2.CH2.CH2OH

31. CH3CHO < CH3COCH3 < CH3COCH2CHO < CH3COCH2COCH3

32. trans-butene-2

33. SOCl2, POCl3, CH3COCl, CH3COCH3

34. O3, KO3, O2

35. n-butanol, MnO2

36. C6H5C CH, C6H5COCH3, C6H5COOH, CHI3

37. (i, iv)

38. (i)

40. C6H5CH(OH)CH3, C6H5COOH

41. CH3 CH3

HC C C OH ; H3CH2C C OH

C 2H 5 C 2H 5
Compounds Containing 22
Oxygen

45. 2, 3

46. R C O C R' ; R C ONa ; R'C ONa

O O O O

51. HCOOC3H7, (CH3)2CHOH

52. C6H5CH = CHC CCHO, CHO.COOH

62. CO2, CH2 = CHCOOH, CH2 = CHCH2OH

63. CHO CH2CHO COCH3 COOH O CH CH2

&

OCH3 OH OH CH3 OH

65. C16H13OH; CH3CH2CH2CH = CH CH = CH.(CH2)8CH2OH (Bombykol)

67. Cl Cl

;;

CHO CHO
O OH

70. H2C = C(CH3).CH2CH3