Carbonyl Compounds

E X E R C IS E 1
Each question contains STATEMENT-1 (Assertion) and STATEMENT-2 (Reason). Each
question has 4 choices (A), (B), (C) and (D) out of which ONLY ONE is correct.
(A) Statement -1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement -1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1.
(C) Statement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True.
1. STATEMENT – 1: Reimer-Tiemann reaction is an example of electrophilic substitution where
the electrophile is dichlorobmethylene.
STATEMENT – 2: Dichloromethylene is electron deficient and is formed by the reaction between
chloroform and alkali.
2. STATEMENT – 1: A ketone may also reduce Fehling’s solution and Tollen’s reagent if there is
an –OH group at -position w.r.t. each.
STATEMENT – 2: Fructose reduces Fehling’s solution and Tollen’s reagent.
3. STATEMENT – 1: Acetic acid does not undergo haloform reaction
STATEMENT – 2: Acetic acid has no alpha hydrogen.
4. STATEMENT - 1 : The benzoin condensation involves intra molecular proton exchange step.
STATEMENT - 2 : The proton exchange step in benzain condensation brings the removal of
better leaving group.
5. STATEMENT - 1: In base promoted halogenation of ketones the bromination and iodination
involves different mechanisms.
STATEMENT - 2 : Rate of bromination and iodination of ketones both depends on concentration
of ketones.
6. STATEMENT – 1: Acetophenone and benzophenone can be distinguished by iodoform test.
STATEMENT – 2: Acetophenone and benzophenone both are carbonyl compounds.
7. STATEMENT – 1: Acetaldehyde reacts with alkaline solution of sodium nitroprusside to give
red colouration.
STATEMENT – 2: Acetaldehyde is good reducing agent.
8. STATEMENT – 1: Reducing sugar give brick red ppt. with fehhing’s solution & show mutarotation.
STATEMENT – 2: During mutarotation, one pure anomer is converted into mixture of two anomers.
9. STATEMENT – 1: A solution of sucrose in water is dextro rotatory but on hydrolysis in presence
of H+, it becomes leavorotatory.
STATEMENT – 2: Inversion of sugar follows first order kinetics.
10. STATEMENT – 1: Hydrate formation of ketones is reversible.
STATEMENT – 2: Stability of hydrates of ketone is very less usually.
11. STATEMENT – 1: Cannizarro reaction is a disproportionation reaction.
STATEMENT – 2: In cannizzarro reaction one mole of aldehyde is oxidized and other is reduced.
12. STATEMENT - 1 : Tertiary alcohol are not form ester with carboxylic acid in the presence of
conc. H2SO4
STATEMENT - 2 : Tertiary alcohol undergoes dehydration in the presence of conc. H2SO4.

ONANCE 35
Carbonyl Compounds
13. STATEMENT - 1 : Formaldehyde is more reactive than benzaldehyde for nucleophilic addition
reaction
STATEMENT - 2 : Delocalisation of -bond of the C=O group in benzaldehyde is due to the
conjugation
14. STATEMENT – 1: Ph–CHO when treated with conc. OH– formation of PhCH2OH and PhCOO–
STATEMENT – 2: It involves hydride transfer, hence one molecule is reduced and another is
oxidized.
15. STATEMENT – 1: HCHO is more reactive than CH3COCH3 towards nucleophilic addition
reaction
STATEMENT – 2: In CH3COCH3, –CH3 shows –I effect.
O

16. STATEMENT – 1: on reduction with NaBH4 in ethanol gives cyclopentanol

STATEMENT – 2: Conjugate addition first occurs followed by second direct addition.

O O
17. STATEMENT – 1: A mixture of on treatment with dil. NaOH
and Me H
Ph Ph
H3C O

gives
H
STATEMENT – 2: The ketone is very hindered and very conjugated and so less reactive than
aldehyde.
18. STATEMENT-1: The addition of amines in aldehyde and ketone is carried out in weakly acidic
medium
STATEMENT-2: In strong acidic medium amines will be protonated hence the nucleophilic
character of amine decrease.
19. STATEMENT-1: Dimethyl sulphide is commonly used for the reduction of an ozonide of an
alkene to get the carboxyl compound.
STATEMENT-2: It reduces the ozonide giving water soluble dimethyl sulphoxide and excess
of it evaporates
20. STATEMENT-1: An aldehydeis more reactive than ketone towards nucleophilic addition reaction.
STATEMENT-2: An aldehyde contains an hydrogen at the carbonyl carbon whereas a ketone
contains two alkyl groups at the carbonyl carbon.

ONANCE 36
Carbonyl Compounds

E X E R C IS E 2
1. The general order of reactivities of carbonyl compounds towards nucleophilic addition reactions
(A) H2C=O > (CH3)2C=O > Ar2C = O > CH3CHO > ArCHO.
(B) H2C = O > CH3CHO > (CH3)2C=O > ArCHO> Ar2C = O
(C) ArCHO > Ar2C=O > CH3CHO > (CH3)2 C = O > H2C = O
(D) Ar2C=O > (CH3)2 =O > ArCHO > CH3CHO > H2C = O
2. Cyanohydrin formation constant will be highest for?

(A) O2N CHO (B) CH3–O CHO

CH3
(C) N CHO (D) COCH3
CH3

O O

OCH3 CH3O H / H2O Ph–C–H, OH

3. X . Identify ‘X’:
OCH3 H / H2O

O
O O O O
OCH3 (B) OH
(A) (C) CH–Ph (D)
O O

O
C 2 H 5O
4. X . X is
H3 O
C–OCH3
O O O=C–CH3

(A) OCH3 (B) OCH3

O O
CH3 O
O OCH3
(C) Cl (D)
OCH3
OCH3
O O
O O O
O
C2H5ONa OEt
5. + EtO–C–OEt
H3 O
Identify name of reaction:
(A) Aldol condenstion (B) Cannizzaro condensation
(C) Crossed Claisen condensation (D) Tischenko reaction

ONANCE 37
Carbonyl Compounds
6. The cyanohydrin of a carbonyl compound on hydrolysis gives lactice acid. The carbonyl compound is
(A) HCHO (B) CH3CHO (C) CH3COCH3 (D) CH3COCH2CH3
7. Arrange the following compounds in decreasing orders of rate of exchange of O18 with H2O18
(X) CCl3CHO (Y) CH3CHO (Z) CH3COCH3 (D) CF3CHO
(A) W > Z > X > Y (B) W > X > Y > Z (C) W > Y > Z > X (D) W > Z > Y > X
CHD2MgI Conc. H2SO4
8. CH2O X Y. In the above reaction compound X & Y respetively will be:
H3 O
OH
(A) CHD–CH2–OH, CHO–CHO (B) CHD2–CH2–OH, CHO–CHO
(C) CHD2–CH2–OH, CD2=CH2 (D) CHD–CH2–OH, CD2=CH2
OH
9. Identify(S) in the following reaction sequence
O O
HOCH2CH2OH Mg H3O
Br–CH2–CH2–C–H P Q R S
H Ether
OH OMgBr O
O O
(A) CH2–CH2–C–H (B) CH2–CH2–C–H

O
CH2–CH2–C–H OMgBr
O O
(C) (D) CH2–CH2–C–H

O
(1) (2) (3)
10. Br C–CH3 CH3–C– –C–CH3 .

O
Reactant
CH2–OH
(A) (1) H (2) Mg/ (3) H–C–O–H/H+
CH2–OH O
O
CH2–OH
(B) (1) H (2) Mg/ (3) H–C–O–Et/H+
CH2–OH O
O
CH2–OH
(C) (1) H (2) Mg/ THF (3) H–C–O–Et/H+
CH2–OH
O
CH2–OH
(D) (1) H (2) Mg/ THF (3) H–C–O–H/H+
CH2–OH
O
O
O O
11. (CH2)4–C–CH3 (CH2)5–CH3
O O
Which of the following reagents is suitable for above conversion?
(A) Zn–Hg/HCl (B) LiAlH4 (C) H2N–NH2/ OH (D) NaBH4

ONANCE 38
Carbonyl Compounds

O
NH2–NH2
12. Write the product of following reaction:
H3C–C
O
Ph Ph Ph Ph
C C
N N N
(A) (B) (C) (D)
N N N
C C
CH3 CH3 CH3
O
CH2–CH2–C–CH3
H H/Ni
13.
NH2

(A) (B) (C) (D)

CH3 CH3 N
N N N
CH3
CH3
14. Which of the following will not undergo aldol condensation?
(A) CH3CHO (B) CH3CH2CHO (C) CD3CHO (D) PhCHO
15. The compound that does not undergo Aldol condensation is
O Me Me O
CH2–CHO Me
O
(A) (B) (C) Me (D)
O
Me O

C–CH3
O3/Zn/H2O NaOH
16. (A) (B) . The reactant (A) will be:

CH2

(A) (B) (C) (D)

17. Compound ‘X’ C4H8O which gives 2, 4-DNP derivative and positive iodoform test is:
O
O O
(A) (B) (C) H3C–CH–C–H (D) OH
H
CH
CHO 3
, OH
O CHO
Ph Cl2 + Ca(OH)2
18. P+ Q R S; ‘S’ will be:

O O
Ph Ph COO
Ph Ph
(A) (B) [Ph–CH2–C–O]2Ca (C) (D)
O CH2OH

ONANCE 39
Carbonyl Compounds

O
KOBr 1. H
19. X +Y Z . Product Z is:
1.
O
O
O COOK
COOH
OH
(A) OH (B) (C) O (D)
CH2OH
O O
20. Compound (X) C4H8O gives positive haloform test but does not give 2, 4-DNP derivative is:
O OH
(A) (B) (C) (D)
OH H O
O
Br2 1. OH
21. In the given reaction sequence A B
H2 O 2. H3 O
O O
OH Br COOH COOH
(A) (B) (C) (D)

22. (X) is the product of mixed aldol condensatoin between benzaldehyde (C6H5CHO) and acetone what
is its structure? O
(A) C6H5–CH=CH– C –CH3 (B) C6H5–CH=C(CH3)2
(C) C6H5–CO–CH2–CH=C(CH3)2 (D) None of these
23. Predict product (C) for the following:
KMnO4/OH HIO4 [O] OH/
A B C
O
CH3
CH3 C–CH3 CH3
(A) (B) (C) (D)
O O CH3
O
O CH3
KOH, H2O
24. CH3CCH2 CCHO Product (C7H10O)

CH3
CH3 CH O
3
CH3 CH3 CH
O O CH3 3
O
(A) CH3 (B) (C) (D)
CH3
CH3 CH3

ONANCE 40
Carbonyl Compounds

BuLi R–X BuLi R''-X HgCl2

25. P Q R S T. The final product ‘T’ is:
O O H2 O
O
(A) (B) S S (C) S S (D) R'—C—R"
R" R" R' Li
R
HCN H3 O H2SO4 B2H6
26. O
H2O2/OH
O
O O OH
(A) (B) (C) (D) OH
HO OH OH O
O
NaBH4
27. The product formed in the reaction is: O C–OCH3
O
(A) HO C–O–CH3 (B) HO CH2–OH

(C) O CH2–OH (D) C–OCH3

NaOH
28. The major product formed in the reaction: C6H5CHO + CH3NO2 
 (X)

CH2NO2
(A) C6H5–CH–CH–NO2 (B) C6H5CHCH2NO2 (C) C6H5CH=CH–NO2 (D) C6H5CH
O CH2NO2
OH
29. What is the final product of this sequence of reactions?
CH2–C–OCH2–CH3
NaOCH2CH3 (1) OH (2) H3O , (3)
CH3–CH2–OH
CH2–C–O–CH2–CH3
O
O
O CHO
(A) (B) O (C) (D)
CH=CH2
O
CH2CH2CH2CH2Br
(CH3)3CO K
30. (X). Identify
Benzene

O O O

(A) (B) (C) (D) O

ONANCE 41
Carbonyl Compounds

E X E R C IS E 3
1. In the given reaction the product is
(1) CH3O Na+ H2 O
CH3–CH2 –C–OCH3 + CH3–C–OCH3
(2) CH3OH
O O
CH3
(A) CH3–CH2–C–CH2–C–OCH3 (B) CH3–C–CH–COOCH3
O O O
CH3
(C) H–C–CH2–CH–COOCH3 (D) CH3–C–CH2–CH3
O O
2. Cannizzaro reaction does not take place with

(A) (CH3)3CCHO (B) CHO (C) (D) CH3CHO

O CHO

CHO
KOH
3. + HCHO (A) + (B)

OCH3 OH
CH2OH COOH CH–CH3

(A) + HCOOK (B) + CH3OH (C) + HCOOK (D) (A) and (B) both

OCH3 OCH3 OCH3

4. In the given Cannizzaro reaction 2Ph–CHO OH Ph–CH2OH + PhCO2– 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 carbocylic acid
(D) The disporportionation of Ph–CH2OH
H2N–OH P2 O 5
5. In the given reaction sequence C6H5CHO A B, A and B are:
H , O
(A) C6H5–CH=N–OH, C6H5CN (B) C6H5–CH=N–OH, C6H5 C –NH2
(C) C6H5–CH=N–OH, C6H5CHO (D) C6H5–CH=N–OH, C6H5–COOH
6. Arrange the stability of given gemdiols in decreasing order:
OH OH OH
I. II. II.
OH OH OH
(A) III > II > I (B) I > II > III (C) III > I > II (D) II > III > I
ONANCE 42
Carbonyl Compounds

OH
O
H O
7. Consider the following reaction H OH The above reaction

is example of
(A) intermolecular hemiacetal formation (B) intramolecular hemiacetal formation
(C) intermolecular acetal formation (D) intramolecular acetal formation
O
HCN LiAlH4
8. In the given reaction A B .A and B will respectively be:
H2 O

OH OH OH OH
(A) CN and CHO (B) CN and CH2NH2

OH CN
NH2 NH2
(C) CN and (D) and

9. Which carbonyl compound has maximum dipole moment?

O O O O

(A) (B) (C) (D)

Br
CH3MgBr
10. In the given reaction the main product will be: NH4Cl/H2O (X)
O

(A) (B) OH (C) (D)

O CH3

CH3MgBr/Cu2I2
11. In the given reaction the main product will be: (Y)
H2O/H
O

(A) (B) OH (C) (D)

O CH3
12. Which of the following structures contains a hemiacetal group?
OH H3C OCH3 OH
O O OCH3
(A) (B) (C) H3C—C—CH3 (D) C6H5–CH
OCH3
OCH3
13. Which of the folloiwng carbonyl compounds when treated with dilute acid forms a stable cation?
O
O
O
(A) (B) (C) (D) C
H C–C–CH
3 3

O
ONANCE 43
Carbonyl Compounds

H2O/H
14. In the given reaction O–CH2CH3 (P). P will be:

(A) OH (B) O` (C) (D) CH2OH

O
15. In the given reaction PhMgBr (X). (X) will be
Cl
BrMgO Ph Ph OH
Ph Ph (C)
(A) (B) (D)
O Cl Cl
CH3 O CH3
16. What are A, B and C in the given reaction?
O
H2 (I equivalent)
H2, Ni A
C LiAlH4
B
O O

(A) in all cases (B) in all cases

OH O OH OH

(C) in all cases (D) , ,

(A) (B) (C)
O 1. BuLi
HS H 2. H3C–Br
17. H3C–C–H + A B. Identify structure of B:
HS 3. HgCl 2/H3O
O O
O
(A) (B) (C) (D) H—C—H
O O
O
H2, Pd–BaSO4
18. X Y . Indntify structure of Y::
isoquinoline
H / H2O
OH OH OH
(A) H (B) (C) CH–CH3 (D) CH3
C=C C=C
H CH3 H H

H2N–NH2/OH
19. In the given reaction O product:

(A) (B) (C) (D) O

ONANCE 44
Carbonyl Compounds

NaCN
20. O (X) . X is:
HCl
CN O OH
HO Cl

(A) (B) (C) (D)

CN CN
OH

PCC CH3NH2 H2/Pd–C

21. (P) . P will be:
H
H CH3
N NH–CH3 O HO NH–CH3

(A) (B) (C) (D)

NO2

Zn–Hg/HCl
22. Product.

O
NO2 NH2
N=O NH2

(A) (B) (C) (D)

O
HS
Ph H PhLi H2, Ni
23. C=O + X. Product X is
CH3CH2–Br
H HS
Ph S Ph S Ph
(A) (B) Ph (B) (D) C=O
H S S
Cl2 + H2O
24. O (P) . (P) will be:

OH O Cl O
Cl Cl
(A) (B) (C) (D)
Cl OH
NaOH
25. O (A). (A) is:
O

(A) (B) O (C) (D)

OH
O
ONANCE 45
Carbonyl Compounds
O O
OH/
26. What is the product (X) of the following reaction? (X)
O
O O O O

(A) (B) (C) (D)

O O
O O
CH3
KOH
27. X CH3 . Find out the structure of ‘X’:

O O
O O
O O
(A) (B) (C) (D) None of these
O
O O O
NaOH
28. Find the product of following reaction: Ph–CH2– C–CH2–Ph + Ph– C – C –Ph

O
O O
Ph Ph Ph Ph Ph–C–C–CH2–Ph
(A) (B) HO OH (C) Ph–C–C–Ph (D) None of these
Ph Ph Ph Ph O

O
Ca(OH)2
29. Find the major product of given reaction: C=O + CH3–CH2–C–H

H
O O
(A) Ph–CH=CH–CH2– C –H (B) CH3CH2–CH= C–C–H
CH3
O O
(C) CH3CH2CH=CH–CH2– C –H (D) Ph–CH= C–C–H
CH3
30. Consider the following sequence of reaction
1. cold KMnO4 NaOH
A B. The product B is:
2. HIO4

O O O

(A) (B) (C) (D)

HO OH
O

ONANCE 46
Carbonyl Compounds

E X E R C IS E 4
1. O3 NaOH
1. A B . A and B are
2. Zn, H2O

OH O O O

(A) and (B) and

OH O O

O O OH
OH
(C) and OH (D) and
O O OH
O
O CH–C6 H5
A 1. LiAlH4
2. B. A and B are
OH, 2. H ,

OH
CH–Ph CH–Ph
(A) Ph–CH3 and (B) Ph–CH3 and

OH OH
O CH–Ph O CH–Ph
(C) C—H and (D) C—H and

3. H NaOH (P). P will be:

H

O
O O O
OH ONa
(A) (B) (C) O (D) None of these
OH OH

CHO NaOH
4. 2 P + Q . P and Q are.
COOH
CH2–OH COO Na CH2–OH CH2–OH
(A) and (B) and
COO Na COO Na COO Na COO Na

COO Na CH2–OH
(C) 2 both (D) both
COO Na COO Na
ONANCE 47
Carbonyl Compounds

Cl O
2Ph3P 2CH3–C–H
5. X Y . Product ‘Y’ is
PhLi

Cl
CH=CH–CH3 CH=CH–CH3 CH=PPh3 CH2–PPh3

(A) (B) (C) (D)

CH2–CH=CH2 CH=CH–CH3 CH=PPh3 CH2–PPh3

O
C2H5O H3 O
6. Y . Product Y is

O O
C=N–H CH–CH2–CN
(A) (B) (C) (D) None of these

O O
1. C2H5O
7. A +B . Identify A and B
2. H3O
O O
O O
(A) + (B) +

O O

(C) + C (D) None of these

EtO
O
MnO2 KCN/EtOH
8. CH2OH X Y . (Y) will be:
H2 O
O O O O O
(A) Ph–C–CH–Ph (B) Ph–C–OK and Ph–CH2OH (C) Ph–C–H (D) Ph–C–C–Ph
OH

O 1. Br2, H2O
9.
2. OH
3. H3O
O O
OH
(A) (B) (C) (D)
Br COOH O

ONANCE 48
Carbonyl Compounds

O3 KOH,
10. A B. Compound B is:
Zn–H2O

CHO
O
(A) CHO (B) C—H (C) CHO (D) OH

OH
11. The given conversion can be performed by which of the following reactions?
O O O

(A) Aldol condensation (B) Michael addition (C) Perkin reaction (D) Reimer-Tiemann reaction
O
O O
C—H
1. C2H5O/C2H5OH
12. (R) would be:
2. R
O O
(A) HCHO (B) H3C–C–H (C) (COOC2H5)2 (D) H–O–OC2 H5
O

13. .
OH OH
Above conversion can be achieved by:
(A) Wolf-Kishner reduction (B) Clemmensen reduction
(C) LiAlH4 (D) NaBH4

H3O
14. A + B ; Compound A and B can be differentiated by:
O
(A) 2, 4-DNP (B) Fehling solution (C) Lucas reagent (D) NaHSO3
O O HO
(1 mole)
H HO CH3MgBr
15. Product:
H H3 O

OH OHO
OH O O O H3 C O O O
(A) H (B) H (C) H (D) H

Mg–Hg ,
16. O X ; Find out final product (X):
H2O,
O OH

(A) (B) (C) (D)

OH
O O
ONANCE 49
Carbonyl Compounds

OH

H3O
17. product:
O
O
OH OH
OH O
(A) (B) (C) H–C–H (D) Both (a) and (c)
OH OH
OH

O LiAlH4 conc. H2SO4

18. (X) ; product (X) of reaction is:
O
OH OH OH
(A) (B) (C) (D)
O O O O
O O
Zn
19. C–H + Br–CH2–C–OEt A . Product A is
H2O

OH O OH O
(A) Ph–CH–CH2–C–OH (B) Ph–CH–CH2–C–OEt
(C) Ph–CH=CH–CH2–OH (D) Ph–CH=CH–CH3
O O

OEt HO OH (1 mole) 2PhMgBr

20. X. X is
H H3 O

O OH Ph O Ph O
O O O HO HO
(A) Ph (B) OEt (C) OEt (D) Ph
Ph

N–OH
conc. H2SO4 LiAlH4
21. (Y). (Y) will be:

H H
N N OH
(A) (B) N—H (C) (D)

22. CH3–CHO–H react most readily with

(A) H2N–NH2 (B) H2N–NH–CO–NH2 (C) Ph–NH–NH2 (D) H2N–OH

ONANCE 50
Carbonyl Compounds

O
1. HCN
23. (A) . Product ‘A’ will be:
2. LiAlH4
3. NaNO2 + HCl
O O O

(A) (B) (C) (D) None of these

O
O
AlCl 3
24. + C–Cl (X). X will be:

(A) C (B) (C) (D)

O
MeONa/MeOH
25. (A) ; find out major product (A):
OH
O O O O

(A) (B) (C) (D)

O O O O
O O OH
CO2H

A
26. . A (reagent) is:

(A) LiAlH4, H ,  (B) OH/ , H (C) H , OH/ (D) NaBH4, H

27. Give the correct sequence of reagents for the following conversion:
O O
Br ?
C–CH3 HO–CH2–CH2 C–CH3

O
CH3OH (excess) Mg/ether H2O/H3 O
(A)
H2SO4
O
Mg/ether H2O/H3 O CH3OH/H
(B)
O
CH3OH (excess) Mg/ether H2O/H3 O
(C)
H2SO4
O
H2O/H3 O CH3OH (excess) Mg/ether
(D)
H2SO4

ONANCE 51
Carbonyl Compounds

NH2 H2
28. Product
Raney Ni
O

(a) (B) (C) (D)

O N N
N
H H H
O 2 NaOH
29. Idenitify the major product of following reaction: Br Br
alcoholic
O
O O
O
(A) (B) (C) C (D)
Br
OH
HO
O CH3CH2OH
30. Find the major product of reaction:
H
HO
OH OH OH OCH2CH3
HO CH3CH2O HO HO
O H
O O
(A) (B) (C) OH (D)
CH3CH2O HO HO HO

ONANCE 52
Carbonyl Compounds

E X E R C IS E 5
1. Match the following column
Column–I (Reaction) Column–II (Characteristic)
O
NaOEt
(A) CH3– C –O–Et (p) shows hydrogen isotopic effect
EtOD
O O
NaOD
(B) Ph– C – C –H (q) gives a compound that exist as stable
D2 O
enol
OH
SOCl2
(C) (r) shows a rearrangement

O
KMnO4
(D) CH3– C –H (s) forms a compound having – COOH
H
group

2. Match the following column

Column - I Column - II
(A) Dieck mann condensation (p) Nitrene
(B) Claisen condensation (q) free radical
(C) Hofmann's Reagent (r) carbocation
(D) Allylic Bromination (s) Carbanion

3. Match the following column

Column- I Column-II
Na2+BF4 – F

(A) Crossed cannizzaro reaction (p)  + BF3 + N2

(q) CH 3COOH   CH 2 (Cl)COOH

Red 'p'
(B) Hell – volhard – zelinsky reaction Cl 2

(C) Baltz – Schiemann reaction (r) C6 H 5 OH  C6 H 5COCl 

NaOH

C6 H 5COOC6 H 5  HCl

(s) C6 H5CHO  CH 2 O 

 ConC  
KOH
(D) Schotten – Bamann

C6 H 5 CH 2OH  HCOOK

ONANCE 53
Carbonyl Compounds

E X E R C IS E 6
Passage–1
Aldehydes undergo disproportionation reaction in presence of aqueous NaOH. Simultaneous oxida-
tion and reduction of a compound is scientifically called as disproportionation. Aldehyde having no -
hydrogen show this reaction called Cannizzaro's reaction. Few exceptions are also there to this
generalisation. The reaction may be represented as :
NaOH
C6H5CHO + C6H5CHO  C6H5COONa + C6H5CH2OH

Intramolecular Cannizzaro's reaction is also possible.
CHO CH2OH
NaOH

CHO COONa
1. The aldehyde having -hydrogen which gives Cannizzaro's reaction is :
(A) CH3–CH2–CHO (B) CH 3 – CH – CHO (C) CH 3 – CH – CHO (D) C2H5–CH2–CHO
| |
CH 3 Cl
CHO NaOH
2. The product formed in the following reaction will be : Product
CHO
CH 2OH CH2OH COONa
(A) (B) (C) (D) all of these
CH 2OH COONa COONa
3. Mixture of C6H5CHO and HCHO is treated with NaOH then Cannizzaro's reaction involves:
(A) oxidation of HCHO (B) reduction of HCHO
(C) oxidation of C6H5CHO (D) None of these
Passage–2
Potassium permanganate in presence of an alkali can hydroxylate a double bond of an alkene by
oxidation, to give a vicinal diol. On the other hand, sodium periodate in aqueous medium can oxidize
vicinal diols to aldehydes or ketones etc. Both the reaction are redox reactions proceed through
cyclic ester formation.
For example:
H
KMnO4 NaIOH
OH H2 O O=C C=O
OH
(1) H OH (2) H H
4. The change in the oxidation state of manganese during the 1st reaction is
(A) VII to IV through V (B) VII to V through VI (C) VII to IV directly (D) VII to V directly
5. Which one of the following is correct regarding oxidation of the reaction 1 and 2 respectively ?
(A) Reaction 1 occurs by 3 electron oxidation and reaction 2 by 2 electron oxidation
(B) Reaction 1 occurs by 5 electron oxidation and reaction 2 by 1 electron oxidation
(C) Reaction 1 occurs by 7 electron oxidation and reaction 2 by 4 electron oxidation
(D) Reaction 1 occurs by 2 electron oxidation and reaction 2 by 5 electron oxidation

ONANCE 54
Carbonyl Compounds
6. Which one of the following is correct regarding the reactions 1 and 2 ?
(A) MnO4  and IO4  are reduced during cyclic ester formation
(B) MnO4  is reduced during cyclic ester formation and IO 4  is reduced before cyclic ester formation
(C) MnO4  is reduced after cyclic ester break down and IO 4  is reduced before cyclic ester breakdown
(D) MnO4  is reduced during cyclic ester formation and IO 4  is reduced during break down of cyclic
ester
Passage–3
Complicated alcohols that cannot be obtained from the market are often synthesized in the lab
with a Grignard reagent. The Grignard reagent is made by reacting metallic magnesium with an
organic halide.Many types of organic halides may be used, including primary, secondary and ter-
tiary alkyl halides and aromatic halides. However, the reagent is a very powerful base and it is
impossible to prepare it from a compound having a hydrogen more acidic than an alkene. The halide
may be a chloride, bromide, or iodide but chlorine based reagents require a special solvent.
The basic formula of a Grignard reagent is RMgX. The magnesium-carbon bond is covalent but
extremely polar making the Grignard reagent a strong nucleophile. It is this characteristic of the
reagent that is used in the synthesis of alcohols.
R' R'
R’ | |
RMgX + O=C  R  C  MgX  H
 R  C  OH  MgX
H | |
H H
In alcohol synthesis the reagent reacts with a carbonyl compound to make the magnesium salt of
the corresponding alcohol. The product is then bathed in dilute mineral acid forming an alcohol and
a water soluble magnesium halide salt.
7. Which of the following compounds would make the best solvent in a Grignard synthesis with an
alkyl bromide-
(A) H2O (B) (C2H5)2O (C) C2H3O2Na (D) C2H5OH
8. Which of the following alcohols would react most strongly with a Grignard reagent ?
(A) CH3OH (B) (CH3)3COH (C) CH3CHOHCH3 (D) CH3(CH2)11CH2OH
9. Which of the following compounds could be reacted with the Grignard reagent shown below to
create a tertiary alcohol

CH2MgBr

O O O
OH
(A) (B) (C) HO (D)
H

ONANCE 55
Carbonyl Compounds

E X E R C IS E 7
1. Predict major products :
CH3 O
CHO   
( i ) Conc . NaOH
(i)  (ii) (
i ) ( C 6 H 5 ) 3 P / CH 3Cl

( ii ) H ( ii ) CH 3 Li / 

O

i ) CH 3  C  CNa
(iii) (  (iv) 
O + HOCH –CH –CH OH 
H


( ii ) H 2 O / H 2 2 2 

 
/ /
(v) O + NH2OH H  (vi) + C6H5NH2 H 

(vii) + HN /
H 

O
2. Give Products of the following reactions :
O O
|| ||
(i) C 6 H 5  C  CH 2  CH 3 CF
3COOOH
 (ii) C 6 H 5  C  H m
 bromoperbenzoic acid

O
CH3
(iii) CF
3COOOH


3. Give the products in each of the following reactions :

CH3
  O
Cl ( 
i) O H COCH3 ( 
i) O H 

(i) C–CH 3 ( ii ) HOH (ii) Br ( ii ) HOH (iii) ( 

i) H O
  ( ii ) D 2 O
|| ( iii ) HOH / H ( iii ) HOH / H
Br ( iii ) HOH / H


O
4. Complete the following reactions :

O O
COOC2H5  
(i) + H2C C 
2 H 5 O / C 2 H 5OH (ii) + CH2=CH–CHO O
H

COOC2H5
O
O

(iii) ( 
i ) ( CH 3 ) 2 CuLi

( ii ) HOH / H
CH3

ONANCE 56
Carbonyl Compounds

5. Identify products in the given reactions :

HO
i ) CHCl 3 / Alc . KOH / 
(i) ( 
 (A) CH
  (B)
2 I 2 / NaOH

( ii ) H 
HO
OH
OCH3
(ii) (
i ) CHCl 3 / Alc . KOH
 (A)

( ii ) H HI/
 
 (B) + (C)

(iii) (
i ) CHCl 3 / Alc . KOH


( ii ) H
N
|
H
OH
(iv) (
i ) CHCl 3 / Alc . KOH


( ii ) H

6. Complete the following reactions :


O H/
(i) C6H5CHO + CH3COOC2H5  

H/
(ii) C6H5–CHO + CH3–CH2–CN O


(iii) O + CH –CH –NO O

H/

3 2 2

H/
(iv) C6 H 5  C  O + O
|
C6H 5
7. Complete the following reactions : :
O
||
(i) C–CH3 (  (C) + (D)
i ) Br2 / NaOH

( ii ) H

CHOH–CH3    (E) + (F)

( i ) CaOCl / HOH
2
(ii) 
( ii ) H

8. Identify (A) to (E) in the given sequence of reaction :

Cl N 
| H

H i ) CH 2  CH  CN
(B) (  (C) H
2O/ H / 
KOH / 
 (D) NH  (E)
 (A)
DMSO ( ii ) HOH  NH
2 2

ONANCE 57
Carbonyl Compounds

E X E R C IS E 8
1. The formation of cyanohydrin from a ketone is an exmaple of: [1990]
(A) Electrophilic addition (B) Nucleophilic addition
(C) Nucleophilic substitution (D) Electrophilic substitution
2. The enolic for of acetone contains: [1990]
(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
3. m-chlorobenzaldehyde on reaction with conc. KOH at room temperature gives: [1991]
(A) Potassium m-chlorobenzoate and m-hydroxybenzaldehyde
(B) m-hydroxybenzaldehyde and m-chlorobenzyl alcohol
(C) m-chlorobenzyl and m-hydroxybenzyl alcohol
(D) Potassium m-chlorobenzoate and m-chlorobenzyl alcohol.
4. Hydrogenation of benzoyl chloride in the presence of Pd and BaSO4 gives: [1992]
(A) Benzyl alcohol (B) Benzaldehyde (C) Benzoic acid (D) phenol
5. An organic compound C3H6O does not give a precipitate with 2,4-Dinitrophenyl hydrazine reagent
and does not react with metallic sodium. It could be: [1993]
(A) CH3CH2CHO (B) CH3COCH3 (C) CH2=CH–CH2OH (D) CH2=CH–O–CH3

6. Under Wolff Kishner reduction conditions, the conversions which may be brought about is?
(A) Benzaldehyde into Benzyl alcohol. (B) Cyclohexanol into Cyclohexane [1995]
(C) Cyclohexanone into Cyclohexanol (D) Benzophenone into Diphenylmethane
7. In the reaction, P is [1995]
CH3 SeO2
CO P + Se + H2O
CH3
(A) CH3COCHO (B) CH3COOCH3 (C) CH3COCH2OH (D) None

OH
8. In the Cannizzaro reactoin given below, 2Ph–CHO Ph–CH2OH + PhCO2– the slowest
step is: [1996]
(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 Ph–CH2OH
9. Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group is:
(A) MeCOCl (B) MeCHO (C) MeCOOMe (D) MeCOOCOMe [1997]
10. In a Cannizaro reaction the intermediate which is the best hydride donor is: [1997]

H H
H H
O O
(A) C6H5–C–O (B) C6H5–C–O (C) (D)
O O
O2N CH3O
OH O

ONANCE 58
Carbonyl Compounds
11. CH3CHO + H2NOH  CH3–CH=N–OH. The above reaction occurs at: [1997]
(A) pH = 1 (B) pH = 4.5 (C) Any value of pH (D) pH = 12
12. Among the following compounds, which will react acetone to give a product containing >C=N–
(A) C6H5NH2 (B) (CH3)3N (C) C6H5NHC6H5 (D) C6H5NHNH2 [1998]
13. The product obtained via oxymercuration (HgSO4–H2SO4) of 1-butyne would be: [1998]

O
(A) CH3CH2– C –CH3 (B) CH3CH2CH2CHO
(C) CH3CH2CHO + HCHO (D) CH3CH2COOH + HCOOH
14. Which of the following will undergo aldol condensation: [1998]
(A) Acetaldehyde (B) Propanaldehyde (C) Benzaldehyde (D) Trideutero acetaldehyde
15. Which of the following will react with water: [1998]
(A) CHCl3 (B) Cl3CCHO (C) CCl4 (D) ClCH2CH2Cl
16. A new carbon-carbon bond formation is possible in [1998]
(A) Cannizzaro reaction (B) Friedel-Crafts alkylation
(C) Clemmensen reduction (D) Reimer-Tiemann reaction
17. Which of the following has the most acidic hydrogen: [2000]
(A) 3-hexanone (B) 2,4-hexanedione (C) 2,5-hexanedione (D) 2,3-hexandione
18. The appropriate reagent for the following transformation: [2000]
O
CH2CH3
CH3

HO HO
(A) Zn(Hg), HCl (B) NH2NH2, OH –
(C) H2/Ni (D) NaBH4
19. A mixture of benzaldehyde and fomraldehyde on heating with aqueous NaOH solution gives: [2001]
(A) benzyl alcohol and sodium formate (B) sodium benzoate and methyl alcohol
(C) sodium benzoate and sodium formate (D) benzyl alcohol and methyl alcohol
20. Compound A(molecular formula C3H8O) is treated with acidified potassium dichromate to form a
product B(molecular formula C3H6O). B forms a shining silver mirror on warming with ammonical
silver nitrate. B when treated with an aqueous solution of H2NCONHNH2.HCl and sodium acetate
gives a product C. Identify the structure of C. [2002]
(A) CH3CH2CH=NNHCONH2 (B) CH3–C= NNHCONH2
CH3

(C) CH3–C=NCONHNH2 (D) CH3CH2CH=NCONHNH2

CH3
21. 1-propanol & 2-propanol can be best distinguished by: [2001]
(A) Oxidation with alkaline KMnO4 followed by reaction with Fehling solution
(B) Oxidation with acedic 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

ONANCE 59
Carbonyl Compounds

CHO OHC
(i) NaOH(excess) 100ºC
22. any one of the product fomred is:
(ii) H+/H2O
CHO OHC

COOH HOOC CH2OH CH2OH

(A) (B) [2003]

COOH HOOC CH2OH CH2OH

O
CH2OH COOH O

(C) (D)

COOH CH2OH O
O
OCOCH3
Acidic
23. OCOCH3 Hydrolysis Products formed by P & Q can be differentiated by:

(A) 2, 4 DNP (B) Lucas reagent (ZnCl2) conc. HCl [2003]

(C) NaHSO3 (D) Fehlings solution
24. The order of reactivity of phenyl Magnesium bromide with the following compounds is
O O O
(I) (II) (III) [2004]
H3C CH3 H 3C H Ph Ph
(A) II > III > I (B) I > III > II
(C) II > I > III (D) All react with the same rate
COOH
CHO
25. CH3COONa What is X? [2005]
+X
MeO MeO
(A) CH3COOH (B) BrCH2, COOH (C) (CH3CO)2O (D) CHO–COOH
26. The smallest ketone and its next homologue are reacted with NH2OH to form oxime. [2006]
(A) Two different oximes are formed (B) Three different oximes are formed
(C) Two oximes are optically active (D) All oximes are optically active
27. Cyclohexene on ozonolysis followed by reaction with zinc dust and water gives compound E.
Compound E on further treatment with aqueous KOH yields compound F. Compound F is
CO2H
(A) CHO (B) CHO (C) COOH (D) CO2H [2007]

28. Statement–1: Glucose gives a reddish brown precipitate with Fehling’s solution. [2007]
Because
Statement-2: Reaction of glucose with Fehling’s solution gives CuO and gluconic acid.

ONANCE 60
Carbonyl Compounds
(A) Statement-1 is True, statement-2 is True; Statment-2 is a correct explanation for statment-1.
(B) Statement-1 is True, statement-2 is True; Statement-2 is NOT a correct explanation for statement-1.
(C) Statement-1 is True, statement-2 is False
(D) Statement-2 is False, Statement-2 is True.
PARAGRAPH
Riemer-Tiemann reaction introduces an aldehyde group, on to the aromatic ring of phenol, ortho to the
hydroxyl group. This reaction involves electrophilic aromatic substitution. This is a general method for
the synthesis of substituted salicyaldehydes are depicted below: [2007]

OH O Na OH
CHO CHO
aq. HCl
[1]
(intermediate)
CH3 CH3 CH3
29. Which one of the following reagents is used in the above reaction?
(A) aq. NaOH + CH 3Cl (B) aq. NaOH + CH2Cl2
(C) aq. NaOH + CHCl3 (C) aq. NaOH + CCl4
30. The electrophile in this reaction is
(A) : CHCl (B) +CHCl2 (C) :CCl2 (D) •CCl3
31. The structure of the intermediate is

O Na O Na O Na O Na
CH2Cl CHCl2 CCl3 CH2OH
(A) (B) (C) (D)

CH3 CH3 CH3 CH3

32. Match the compounds/ion in column I with their properties/reaction in Column–II.Indicate your an-
swer by darkening the appropriate bubbles of the 4×4 matrix given in the ORS. [2007]
Column–I Column–II
(A) C6H5CHO (P) gives precipitate with
2,4,-dinitrophenylhydrazine
(B) CH3CCH (q) gives precipitate with AgNO3
(C) CN– (r) is a nucleophile
(D) I– (s) is involvedin cyanohydrin formation

PARAGRAPH
In the following reaction sequence products I, J and L are formed. K represents a reagent.
1. Mg/ether
Cl H2
1. NaBH4 2. CO2 K L
Hex-3-ynal I J Me Pd/BaSO4
2. PBr3 3.H3O+ O quinoline
33. The structure of the product I is [2008]
Me
(A) Me Br (B)
Br
Me
(B) Me (D) Br
Br

ONANCE 61
Carbonyl Compounds
34. The structure of compound J and K, respectively, are [2008]

Me OH
(A) COOH and SOCl
2
(B) Me and SO2Cl2
O
Me Me
(C) and SOCl2 (D) COOH and CH SO Cl
3 2
COOH
35. The structure of product L is [2008]
Me CHO
(A) (B) Me CHO
CHO
(C) (D) Me CHO
Me

PARAGRAPH
A tertiary alcohol H upon acid catalysed dehydration gives a product I. Ozonolysis of I leads to
compounds J and K. Compound J upon reaction with KOH gives benzyl alcohol and a compound L,
whereas K on reaction with KOH gives only M.
O
H3C Ph
M=
Ph H
36. Compound H is formed by the reaction of [2008]
O O

(A) Ph CH3 + PhMgBr (B) Ph CH3 + PhCH2MgBr

O Me Me
(C) Ph H + PhCH2MgBr (D) Ph H + Ph MgBr
37. The structure of compound I is [2008]

Ph CH H3 C Ph Ph CH3 H3C CH3

3
(A) (B) (C) (D)
H Ph H Ph H CH 2Ph Ph H
38. The structure of compounds J, K and L, respectively, are [2008]
(A) PhCOCH3, PhCH2COCH3 and PhCH2COO–K+ (B) PhCHO, PhCH2CHO and PhCOO–K+
(C) PhCOCH3, PhCH2CHO and CH3COO–K+ (D) PhCHO, PhCOCH3 and PhCOO–K+
PARAGRAPH
A carbonyl compound P, which gives positive iodoform test, undergoes reaction with MeMgBr fol-
lowed by dehydration to give an olefin Q. Ozonolysis of Q leads to a dicarbonyl compound R, which
undergoes intramolecular aldol reaction to gived predominantly S.
1. MeMgBr 1. O3 1. OH
P +
Q +
R S
2. H , H2O 2. H , H2O 2.
3. H2SO4,
39. The structure of the carbonyl compound P is [2009]
O
Me
(A) (B) (C) (D)
O Me O Me O Et Et

ONANCE 62
Carbonyl Compounds
40. The structure of the product Q and R, respectively, are: [2009]

O O

H H
(A) Me ,
COMe (B) , CHO
Me Me Me Me Me Me Me Me

O O
Me
H CH3
(C) , CHO (D) , CHO
Me Et Me Et
Me Me Et
41. The structre of the product S is [2009]

O O O
Me
(A) (B) (C) (D)
O
Me Me Me Me
Me

ONANCE 63
Carbonyl Compounds

E X E R C IS E 9
NaOC2H5 in absolute
1. C6H5–CHO + CH3–COOC2H5 C2H5 OH and heat (D) [1995]

CH3CH2 (i) KCN/H2SO4

2. C=O (ii) LiAlH D [1996]
4
H
3. Acetophenone on reaction with hydroxylamine-hydrochloride can produce two isomeric oximes. Write
structures of the oximes. [1997]
4. An aldehyde (A) (C11H8O), which does not undergo self aldol condensation, gives benzaldehyde and
two mole of (B) on ozonolysis. Compound (B), on oxidation with silver ion, gives oxalic acid. Identify
the compounds (A) and (B). [1998]
O
O CHC6H5
5. (C) (i) LiAlH4 [1998]
(D)
(ii) H+, heat
6. What would be the major product in each of the following reaction? [2000]

Ph
Base
O

Br
7. Identify (A), (B) and (C) and give their structures. [2000]

CH3 Br 2
CH3
A+B
NaOH
O H+
C(C7H12O)

8. Five isomeric para-disubstituted aromatic compounds A to E with molecular formula C8H8O2 were
given for identification. Base on the following observations, give structure of the compounds.
(i) Both A and B form a silver mirror with Tollen’s reagent; also B gives a positive test with FeCl3
solution [2002]
(ii) C gives positive iodoform test.
(iii) D is readily extracted in aqueous NaHCO3 solution
(iv) E on acid hydrolysis gives 1,4-dihydroxybenzene.

9. Write structures of the products A, B, C, D and E in the following scheme. [2002]

O

CH2CH2CH3 Cl2 /FeCl3 Na–Hg HNO3/H2SO4

A B C
HCl
Cl
CH2=CHCH2O–Na+ H2/Pd/C
D E

ONANCE 64
Carbonyl Compounds

HCl
10. C6H12 C6H13Cl + (C) [2003]
(A) (B)
Alc. KOH ozonolysis
(D) (E)
ozonolysis
(A) (F) + (G) NaOH HCOONa + 1º alcohol.
(D) is isomer A. E gives negative test with Fehling solution but gives iodoform test. F and G gives
Tollen’s test but do not give iodoform test. Identify A to G.

11. Which of the following disaccharide will not reduce Tollen’s reagent? [2005]

CH2OH CH2OH HOH2C CH2OH

HO O OH HO O OH
HH HH
O O
(A) H HO H HO (B) H HO OH H
H O H H O H
OH H OH H OH H H OH

ONANCE 65
Carbonyl Compounds

E X E R C IS E 10
(PREVIOUS YEAR AIEEE QUESTIONS)

1. Maximum dehydration takes place that of [AIEEE-2002]

O O O CH3
OH
(A) (B) (C) (D)
OH OH
OH
2. On vigorous oxidation by permanganate solution (CH 3 )2 C  CH  CH 2CH 3 gives [AIEEE-2002]

OH OH CH 3
| | \
(A) CH 3  C  CH  CH 2 CH 3 (B) CHCO 2 H  CH 3 COOH
| /
CH 3
CH 3

CH 3 CH 3
\ \
(C) CHOH  CH 3 CH 2 CH 2 OH (D) C  O  CH 3 CH 2 COOH
/ /
CH 3 CH 3

3. Which one of the following is reduced with zinc and hydrochloric acid to give the corresponding
hydrocarbon ? [AIEEE-2004]
(A) Ethyl acetate (B) Acetic acid (C) Acetamide (D) Butan-2-one
4. Which one of the following undergoes reaction with 50% sodium hydroxide solution to give the
corresponding alcohol and acid?
(A) Phenol (B) Benzoic acid (C) Butanal (D) Benzaldehyde

5. The best reagent to convert pent–3–en–2–ol into pent–3–into–2–one is -

[AIEEE-2005]
(A) Acidic dichromate (B) Acidic permanganate
(C) Pyridinium chloro–chromate (D) Chromic anhydride in glacial acetic acid

O O
6. The reaction R–C + Nu R–C + X is fastest when X is: [AIEEE-2005]
X Nu
(A) OCOR (B) OC2H5 (C) NH2 (D) Cl

7. Reaction of cyclohexanone with dimethylamine in the presence of catalytic amount of an acid forms a
compound if water during the reaction is continuously removed. The compound formed is generally
known as [AIEEE-2005]
(A) an amine (B) an imine (C) an enamine (D) a Schiff's base

8. The increasing order of the rate of HCN addition to compounds A – D is - [AIEEE-2006]

(a) HCHO (b) CH 3COCH3 (c) PhCOCH3 (d) PhCOPh
(A) d < b < c < a (B) d < c < b < a (C) c < d < b < a (D) a < b < c < d

ONANCE 66
Carbonyl Compounds
9. In the following sequence of reactions, [AIEEE-2007]
P + I2 Mg HCHO H2 O
CH3CH2OH A B C D. The compound D is
Ether
(A) n-propyl alcohol (B) propanal (C) butanal (D) n-butyl alcohol
10. In the following sequence of reactions, the alkene affords the compound 'B' [AIEEE-2008]
O3 H2O
CH3CH=CHCH3 A B. The compound B is
Zn
(A) CH3COCH3 (B) CH3CH2COCH3 (C) CH3CHO (D) CH3CH2CHO

11. Which of the folowing on heating with aqueous KOH, produces acetaldehyde ? [AIEEE-2009]
(A) CH3COCl (B) CH3CH2Cl (C) CH2ClCH2Cl (D) CH3CHCl2

ONANCE 67
Carbonyl Compounds

ANSWERSHEET
Daily Practice Problems - 03
1. D 2. B 3. B

Daily Practice Problems - 05

1. B 2. C 3. D 4. D 5. C 6. B
7. C 8. B 9. C 10. D 11. D 12. A
13. A 14. B 15. A 16. D 17. D 18. C
19. B 20. C

Daily Practice Problems - 06

1. C 2. C 3. C 4. D 5. C 6. D
7. B 8. B 9. B 10. B 11. C 12. C
13. D 14. C 15. A 16. D 17. C 18. A
19. D 20. C

Exercise - 01
1. A 2. B 3. C 4. A 5. D 6. B
7. B 8. A 9. B 10. A 11. A 12. A
13. A 14. A 15. C 16. A 17. A 18. A
19. A 20. B

Exercise - 02
1. B 2. A 3. C 4. D 5. C 6. B
7. B 8. C 9. C 10. C 11. C 12. A
13. B 14. D 15. C 16. B 17. A 18. C
19. C 20. A 21. C 22. A 23. A 24. C
25. D 26. A 27. A 28. C 29. B 30. B

Exercise - 03
1. D 2. D 3. A 4. B 5. A 6. B
7. B 8. B 9. D 10. B 11. A 12. A
13. D 14. B 15. B 16. B 17. C 18. D
19. C 20. C 21. A 22. D 23. B 24. D
25. C 26. B 27. B 28. A 29. D 30. B

ONANCE 68
Carbonyl Compounds

Exercise - 04
1. B 2. D 3. B 4. A 5. B 6. A
7. B 8. A 9. B 10. B 11. B 12. D
13. A 14. B 15. C 16. D 17. D 18. C
19. B 20. A 21. A 22. A 23. C 24. B
25. B 26. B 27. A 28. C 29. C 30. D

Exercise - 05
1. A-pq, B-prs, C-r, D-ps 2. A-s, B-s, C-p, D-q 3. A-s, B-q, C-p, D-r

Exercise - 06
1. B 2. B 3. A 4. A 5. A 6. D
7. B 8. A 9. D

Exercise - 08
1. B 2. A 3. D 4. B 5. D 6. D
7. A 8. B 9. A 10. D 11. B 12. A,D
13. A 14. ABD 15. B 16. BD 17. B 19. A
20. A 21. C 22. C 23. D 24. C 25. C
26. B 27. A 28. C 29. C 30. C 31. B
32. A-ps, B-q, C-qrs, D-qr 33. D 34. A 35. C
36. B 37. A 38. D 39. B 40. A 41. B

Exercise - 09
CH3CH2 OH
1. C6H5CH=CHCOOC2H5 2. C
H CH2NH2
3. C6H5–C–CH3 and C6H5–C–CH3
N–OH HO–N
syn anit(isomes)

CHO CHO Ag+

Ozonolysis COOH
4. +
COOH
COOH
(A) (B)
(Oxalic acid)

CHC6H5 Ph Ph
C6H5CHO Base
5. 6. O
+ Base O
(C) (D)
Br
ONANCE 69
Carbonyl Compounds

O O O
CH3 CH3 CH3
Br2 + NaOH
7. C–CH3 COONa + CHBr3
O
(A) (B) (C)
O
CHO CHO CH2CHO C–CH3 COOH O–CH=CH2

8. A. or B. C. D. E.

OCH3 CH2OH OH OH OH OH

O
NO2
C–Pr Bu Bu
9. A. B. C.
Cl Cl Cl
Cl Cl Cl
NH2
NO2 Bu
Bu
D E
Cl
Cl O–Pr
O–CH2–CH=CH2
10. Me3C–CH=CH2 Me2C–CHMe2 + Me3C–CH–Me
Cl Cl
(B) (C)
alc. KOH
Ozonolysis NaOH
(A) HCHO + Me2C–CHO
(F) (G)
HCOONa + Me3C–CH2OH (1ºalcohol)

11. In structure P both the rings are present in acetyl from therefore it will not hydrolyse in solution
that why Fehling solution cannot react with this.
In structure Q one ring present in the form of hemiacetal. This will hydrolysed in solution it can
reduce Fehling solution.

Exercise - 10
1. B 2. D 3. B 4. D 5. C 6. D
7. C 8. D 9. A 10. C 11. D

ONANCE 70