CARBONYL COMPOUND

EXERCISE-1 (Subjective Questions)

Q.1 Some Grignard reagents react with ethyl orthoformate, followed by acidic hydrolysis, to give aldehydes.
Propose mechanisms for the two steps in this synthesis.
O CH 2CH 3 O CH 2CH 3 O
| | ||
H C O CH 2 CH 3 + R – Mg – X R C O CH 2CH 3 H3O
R C H
| |
O CH 2CH 3 H
ethyl orthoformate acetal aldehyde

Q.2 Suggest a resonable mechanism for each of the following reactions :

O
||
NaOCH3 (CH 3 ) 3 CCCH 2OCH 3
CH 3OH (88%)

Q.3 Write the product of the following reactions:

O
||
(a) CH 3 CH 2 C Cl (i ) DIBAL H hexane , 78 C
(ii ) H 2O

C N
(b) (i ) DIBAL H hexane , 78 C
(ii ) H 2O

Q.4 Complete the following :

O
SOCl 2 (A) (i ) DIBAL H hexane , 78 C (B)
OH (ii ) H 2O

Q.5 Write down the product of the following reactions:

OH
PCC
(a) CH

CH3
PCC
(b) H—C OH
Et

Q.6 Complete the following sequence:

CH 3 CH CH CH 2 OMDM (A) PCC (B)
|
CH 3

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 CARBONYL COMPOUND

Q.7(a) Arrange the following compounds in decreasing order of Keq. for hydrate formation.
O
||
C6H5COCH3 Cl C CH3
(1) (2)
O O
|| ||
NO2 C CH3 CH3 C CH3
(3) (4)

Q.7(b) Equilibrium constants for the dissociation (Kdiss) of cyanohydrins according to the equation
OH O
| ||
RCR ' RCR ' + HCN
|
CN
Cyanohydrin Aldehyde Hydrogen
or ketone cyanide
have been measured for a number of cyanohydrins. Which cyanohydrin in each of the following pairs has
the greater dissociation constant ?
OH OH OH OH
| | | |
(i) CH 3CH 2CHCN or (CH 3 ) 2 CCN (ii) C6 H 5CHCN or C6 H 5CCN
|
CH 3
Q.8 Each of the following reactions has been reported in the chemical literature. Write the structure of the
product (s) formed in each case.
O
|| KOH
C 6 H 5CH 2SH
(a) H3C CH2 (b) Cl CH + , ethanol
NaOH , H 2 O

Q.9 Suggest appropriate reagents for following conversion.

O OH
O
(a) ? O
C—H
C—H
O OH
O C—OEt O C—H
(b) ?

H
Q.10 Give the structure of the substance for each of the following reaction :

NaOH /
(a) (X) NaOH / (b) (Y) NaOH / (c) (Z)

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 CARBONYL COMPOUND

Q.11 Give structure for the products of the reaction when butanal is treated with each of the following reagents

(a) A g( NH3 ) O H then HOH / H (b) O H / HOH ,

(c) NH2OH / H (d) C6H5Li then HOH
(e) C6H5CHO, O H , (f) CH CNa then HOH / H
(g) CH2OH – CH2OH, H
(h) SH – CH2 – CH2 – CH2 –SH then Raney Ni/H2
(i) CH3MgBr then H2O (j) HCN (k) NaBH4
Br
|
(l) CH 3 CH 2 CH COOC2 H 5 and Zn then H2O/ H

Q.12 A synthesis that begins with 3,3-dimethyl-2-butanone gives the epoxide shown. Suggest reagents
appropriate for each step in the synthesis.
O O OH
|| || |
58% 54% 68%
(CH 3 )3 CCCH 3 (CH 3 )3 CCCH 2 Br (CH 3 )3 CCHCH 2 Br (CH 3 )3

Q.13 Outline resonable mechanisms for each of the following reactions :

KOC( CH3 )3
benzene

Q.14 IdentifyAto E in the given sequence of reaction :

KOH / Br2
SeO 2 / CH 2Cl 2 (A) CF3COOOH (B) H 2O (C) NH3 / (D) (E)

Q.15 Synthesis of each of the following compounds have been reported in the chemical literature. Using the
indicated starting material and any necessary organic or inorganic reagents, describe short sequence of
reactions that would be appropriate for each transformation.
(a) 1,1,5-Trimethylcyclononane from 5,5-dimethylcyclononanone

(b) from

Q.16 Write mechanism.

(i ) RO
+
(ii ) ROH

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 CARBONYL COMPOUND

Q.17 Consider following compounds & write number of compounds which can reduce Tollen's reagent.

CH 2–OH
OCH3 O
C=O CH 2OH
H3C– CH OCH3
O CH – OH HO
OCH3 OH HO OH
CH – OH
CH – OH
CH 2–OH

OH

Ph – CH = O OH
O O

Q.18 Consder following compounds and give number of compounds which can reduce Tollen's reagent.

CH2OH
H O H
H
H H CH2OH
O OH O O H
OCH 3 H OH H
H H
O OH
H OH
OH OH

H
H3C–CH2–C C–CH2–CH3
O O O
CH2OH
C=O
CH–OH
CH–OH OH
H3C–CH2–CH2–C CH OH
CH–OH O
CH2–OH

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 CARBONYL COMPOUND

Q.19 Predict the product of the reaction of propanal with each of the following :
(a) Lithiumaluminumhydride (b) Sodium borohydride
(c) Hydrogen (nickel catalyst) (d) Methylmagnesium iodide, followed bydilute acid.
(e) Sodium acetylide, followed by dilute acid
(f) Phenyllithium, followed bydilute acid. (g) Methanol containing dissolved hydrogen chloride
(h) Ethylene glycol, p-toluenesulfonic acid, benzene
(i) Aniline (C6H5NH2) (j) Dimethylamine, p-toluenesulfonic acid, benzene
(k) Hydroxylamine (l) Hydrazine
(m) Chromic acid
(n) p-Nitrophenylhydrazine (o) Semicarbazide
(p) Ethylidenetriphenylphosphorane [ (C6 H 5 )3 P ]
(q) Sodium cyanide with addition of sulfuric acid

Q.20 Show how you would accomplish the following synthesis efficiently and in good yield.You mayuse any
necessary reagents.

(a) (b)

(c) (d)

(e) (f)

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 CARBONYL COMPOUND

EXERCISE-2 (Objective Questions)

[SINGLE CORRECT CHOICE TYPE] [

Q.1 Acetophenone can be obtained by the distillation of:

✓ (A) (C6H5COO)2Ca .
(B) (CH3COO)2Ca e

(C) (C6H5COO)2Ca and (CH3COO)2Ca (D) (C6H5COO)2Ca and (HCOO)2Ca

E
'
r
r

Q.2 Which one of the combinations will give propanaldehyde on dry distillation?
(A) (C6H5COO)2Ca and (HCOO)2Ca (B) (CH3COO)2Ca and (CH3CH2–COO)2Ca
(C) (CH3–CH2–COO)2Ca and (HCOO)2Ca (D) (CH3COO)2Ca and (CH3COO)2Ca

Q.3 Gem dihalide on hydrolysis gives:

(A) Vic diol (B) Gem diol (C) Carbonyl compound (D) Carboxylic acid

Q.4 Which of the following is not correct about P2.

O
Mg H
H 2O
P1 P2

(A) It is a spiro compound (B) It is a Ketone

(C) It can show tautomerism (D) It is an alkene

Q.5 In the given reaction:

r OH OH
| |
CH 3 CH — C CH 3 HIO 4
(a) + (b)
|
CH 3
(a) and (b) respectively be:
(A) CH3CHO and CH3CHO (B) CH3COCH3 and CH3CHO
(C) CH3COCH3 and CH3COCH3 (D) CH3COOH and CH3COCH3

Q.6 Cyanohydrin of which compound on hydrolysis will give lactic acid?

(A) C6H5CHO (B) HCHO (C) CH3CHO (D) CH3–CH2–CHO

Q.7 What will be the major product of the following reaction?

Hg 2 / H / H 2O
- M e–C C – Ph (P)
O O
|| ||
(A) Me CH 2 C Ph (B) Me C CH 2 Ph

(C) Me – CH = CH – Ph (D) Me CH CH 2 Ph
|
OH

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 CARBONYL COMPOUND

O
C
Q.8 Cl H 2 / Pd
(P)
✓ BaSO 4

O
CH2OH C–H
(A ) (B)

O
CH2 –OH
C –OH
(C) (D)

O
C–NH2 P2O5 / (i ) SnCl 2 / HCl
Q.9 (A) (B)

:
( ii ) H / H 2O

What will be the structure of B?

O
C N C–H
(A) (B)

CH2 –NH2
(C) (D) None of these

KOH
Q.10 Ph – C CH3 P,,
HCl ( excess ) ( excess )
P is
(A) Ph CH 2 C H (B) Ph C CH 3
|| ||
O O

(C) Ph CH CH 3 (D) None of these

| |
OH OH

i
Q.11 Arrange these compounds in decreasing order of reactivity for the nucleophilic addition reaction:
(I)Acid chloride (II)Aldehyde (III) Ketone (IV) Ester
Select the correct answer from the codes given below:
(A) I > II > III > IV (B) IV > III > II > I (C) III > II > I > IV (D) I > IV > II > III

Q.12 Grignard reagents do not give carbonyl compounds with :

(A) CO2 (B) RCOCl (C) RCN (D) RCOOR

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Q.13 In the given reaction:

C6 H 5 C H NH 2OH / H
|| [X]
O
[X] will be:
(A) Only syn oxime (B) Onlyanti oxime
(C) mixture of syn and anti oxime (D) secondary amide

Q.14 Compound formed by the reaction of furfural ( ) with ethanol is

(A) an aldol (B) an acetal (C) a ketal (D) a hemiacetal

Q.15 Acetal or ketal is:

(A) Vic dialkoxy compound (B) , -dialkoxy compound
(C) -alkoxy alcohol (D) Gem dialkoxy compound

Q.16 CH 3 C H NaHSO3 P,,

||
O
P is
(A) H 3C CH 2 (B) H3C–CH–OH (C) H 3C CH OH (D) H3C–CH–ONa
| O | O
OSO3 Na O–S–Na SO3 Na O–S–H
O O

O
Q.17 + Ph – NH – NH2 H

✓ formed product is
N – Ph
(A) NH2 (B) N–NH–Ph

(C) N–Ph (D) None of these

Q.18 Carbonyl compound give semicarbazone on reaction with

(A) Ph – NH – NH2 (B) H2N–NH NO2

O2 N

(C) H 2 N NH C NH 2 (D) NH2 – OH

||
O

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 CARBONYL COMPOUND

O HO
Q.19 + dry HCl X,
HO
X is :
O
(A) O (B)

O O
CH
(C) O (D) O

Q.20 Acetone can be converted into pinacol by :

(A) (i) Mg/Hg (ii)H2O (B) Zn/Hg/HCl
(C) Red P / HI (D)All of these

Q.21 In the given reaction

OH
|
NaOH
X+Y CH 3 CH CH CHO
5 C |
CH 3
(X) and (Y) will respectively be:
(A) CH3–CH2–CHO and CH3–CH2–CHO (B) CH3–CHO and CH3–CH2–CHO

CH 3
|
(C) CH3–CHO and CH3–CHO (D) CH3–CHO and CH 3 C CHO
|
CH 3
Q.22 Number of products (excluding stereoisomers) in the given reaction :
OH
C6H5CHO + CH3–CHO Product
will be
(A) One (B) Three (C) Two (D) Four

Q.23 In the reaction :

OH /
+ [X]
[X] will be :

(A) (B)

(C) (D)

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Q.24 Cross cannizzaro reaction is example of :

(A) Redox reaction (B) Disproportionation (C) Both (A) and (B) (D) Only oxidation

Q.25 Product of Perkin reaction is:

(A) , -unsaturated aldehyde (B) -cyclohexyl , -unsaturated aldehyde
(C) -Aryl- , -unsaturated acid (D)All of these

Q.26 The product of the reaction:

NO2 CHO + (C6H5–CH2CO)2O C6 H5 CH 2COONa / X, X will be ?

(A) C6H5–CH =CH–COOH (B) NO2 CH=CH–COOH

(C) C6H5–CH = C – COOH (D) NO2 CH C COOH

|
C6 H 5

NO2

CH 2OH
|
Q.27 Acetaldehyde can be converted into HO CH 2 C CH 2OH by which reagent?
|
CH 2OH
(A) KOH (B) KOH followed by LAH
(C) excess of HCHO and KOH (D) KCN followed by SBH

Q.28 The given reaction

( i ) Zn
C6H5–CHO + Br–CH2–COOC2H5 C6H5–CH=CH–COOC2H5
( ii ) HOH / NH 4Cl
( iii )

is known as :
(A) Perkin reaction (B) Knoevenagel reaction
(C) Reformatsky reaction (D) Claisen-Schmidt reaction

Q.29 In the given reaction

OH
|
( i ) Zn
C6H5CHO + X C6H 5 CH CH 2 COOC 2 H 5
( ii ) HOH / NH 4Cl
[X] will be:
(A) CH3–COOC2H5 (B) CH3–CH2–COOC2H5

(C) Br–CH2–COOC2H5 (D) CH–COOC2H5

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Q.30 Consider the given reaction :

O O
|| C6 H5COOOH ||
CH 3 C CH 3 CH 3 C O CH 3
The above reaction is known as :
(A) Baeyer-villiger oxidation (B) Oppenaur oxidation
(C) Periodate oxidation (D) Peroxide oxidation

Q.31 LiAlH 4 product is

:
(A) CH2CH2CHO (B) CH=CHCH2OH

(C) CH2CH2CH2OH (D) CH2CH2CH2OH

Q.32
In the given reaction:
NaBH 4
H2C O (X)

(i) BH3
(excess)
(ii) CH3COOH

(Y)
(X) and (Y) are :

(A) CH2 OH and HO CH2 O

(B) CH3 O and HO CH2 O

(C) CH2 OH and CH3 OH

(D) CH2 OH and O

Q.33 In the reaction sequence, [X] is ketone :

CH 3
KMnO 4 / H /
|
[X] HOOC – (CH2)3– CH COOH
[X] will be:

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

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 CARBONYL COMPOUND

[(CH 3 ) 2 CHO ]3 Al
Q.34 + A.
C

Ais:

(A) (B)

(C) (D)

Q.35 In the given reaction

SeO 2 [X]

[X] will be:

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

r

Q.36 When D-glucose is treated with HNO3 then the product is:

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

Q.37 When D-glucose is treated with Br2 water then the product is:

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

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 CARBONYL COMPOUND

O
Q.38 CH 3–CH–C–C 6H 5
i
MCPBA [X] as major product [X] will be :

✓ CH3

O O
CH3–CH–C–OC6H5 CH3–CH–O–C–C 6H 5
(A) (B)
CH3 CH3

O O
(C) (D) C6H5–CH2–O–C–CH2–CH3
CH3–CH2–O–C–CH2–C6H5

O O
Q.39 CH3CO3H
(A) H / H 2O
(B) (C)
CH3–C–C–Ph
B and C are :
(A) CH3OH and C6H5COOH (B) PhOH and CH3COOH
(C) CH3COOH and C6H5COOH (D) PhOH and MeCOOH

Q.40 The given reaction

Aluminium tertiary butoxide

Acetone

is known as :
(A) Kolbe reaction (B) Tischenko reaction (C) MPV reaction (D) Oppeneur oxidation

Q.41 Which one of the following compounds will give dimethyl glyoxal with SeO2:
(A)Acetone (B)Acetophenone (C) Ethyl methyl ketone (D) Propanaldehyde

Q.42 Which of the following is correct increasing order of the boiling point of given compounds ?
CH 3 C CH 3 C2H5 – O – CH3 CH3–CH2–CH2–CH2–OH
||
O
(I) (II) (III)
(A) III < I < II (B) I < II < III (C) II < I < III (D) I < III < II

Q.43 Boiling points of carbonyl compounds are higher than those of alkanes due to
(A) Hydrogen bonding (B) Dipole-dipole interactions
(C) Vander Waal’s forces (D)All of these

Q.44 Carbonyl compounds show nucleophilic addition reaction with

(A) HCN (B) NaHSO3 (C) CH3MgCl (D)All of these

Q.45 Which poisonous gas form after air oxidation of chloroform?

(A) CO (B) SOCl2 (C) COCl2 (D) SO2Cl2

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alc.KCN PCC OH /
Q.46 Ph C H
||
O

Final product is

Ph Ph Ph Ph
| | | |
(A) Ph C CHO (B) Ph C COO ¯ (C) Ph C C H (D) Ph C — C Ph
| | || | | ||
OH OH O O¯ OH O

O
OD/ D 2O CH 2 PPh 3
Q.47 P

P is
OH
CH 3 O O CH2
D D D D D D
(A) D D (B) D D (C) D D (D) D D
D D

O
PCl5 KOH
Q.48 M
( 2 eq .)
M on reaction with PhMgBr, followed by acidification gives
Ph Ph
(A) (B) (C) OH (D) OH
OH OH Ph Ph

Q.49 Which carbonyl compound has better electrophilic site at carbonyl carbon?

(A) C – CH3 (B) H C H

||
O O

(C) Cl3C C H (D) C–H

||
O O

Q.50 Metaformaldehyde is:

(A) Dimer of HCHO
(B) Trimer of formaldehyde
(C) Tetramer of formaldehyde
(D) Polymer in which number of HCHO unit is more than 100

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Br2 water
Q.51 C3H6 O +ve test (Br2 water
(P) decolourises)
2, 4-DNP
–ve test
Na
H2
What is structure of P ?
H O
(A) (B) (C) CH3 (D)
O OH O

Q.52 Schiff's reagent is used for the differentiation between:

(A) HCHO and CH3CHO
(B) CH3COCH3 and CH3CHO
O O
|| ||
(C) C6 H 5 CH 2 C CH 3 and C6 H 5 C CH 2 CH 3
(D) HCHO and C6H5CHO

Q.53 Which will give silver mirror test withTollens reagent :

(A) C6H5CHO (B) CH3–CHO (C) HCOOH (D)All of these

Q.54 Acetaldehyde cannot give:

(A) Iodoform test (B) Lucas test (C) Benedict test (D) Tollens test

O O
|| ||
Q.55 CH3 C H and CH 3 C CH 3 is differentiated by
(A) Tollen's reagent (B) Lucas test (C) Iodoform (D) NaHSO3

Q.56 Formalin is the commercial name of

(A) Formic acid (B) Fluoroform
(C) 40% aqueous solution of methanol (D) Para formaldehyde

Q.57 Which compound is used for preparation of Bakelite ?

(A) Methanal (B) Ethanal (C) Benzaldehyde (D) VinylAcetate

[MULTIPLE CORRECT CHOICE TYPE]

Q.58 Which one of the following is mixed ketone:
O O
|| ||
(A) CH 3 C CH 3 (B) CH 3 CH 2 C CH 3

O O
|| ||
(C) Ph C CH 3 (D) CH 3 C 6 H 4 C CH 2 Ph

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Q.59 Stability of hydrates of carbonyl compounds depends on:

(A) Steric hindrance

=
(B) Presence of –I group on gemdiol carbon
(C) Intramolecular hydrogen bonding
(D) angle strain in carbonyl compound

Q.60 Consider the structure of given alcohol:

OH
|
C6 H 5 C CH 3
|
C2 H5
This alcohol can be prepared from:
O O
|| ||
(A) C 6 H 5 C CH 3 and C2H5MgBr (B) CH 3 CH 2 C CH 3 and C6H5MgBr

O O
|| ||
(C) C 6 H 5 C C 2 H 5 and CH3MgBr (D) C 6 H 5 C Cl and C2H5MgCl

Q.61 Acetone give addition elimination reaction with

(A) Hydroxyl amine (B) Sodiumbisulphite
(C) Hydrogen sulphide (D)Ylide (Wittig reagent)

( i ) Ph 3P
Q.62 (A)
(ii ) BuLi
(iii ) ( B)
In above reaction (A) & (B) will be -

(A) & CH3CHO (B) CH3CH2Cl &

(C) & HCHO (D) & CH3CHO

Q.63 Which of the following form stable hemiketal

O
||
(A) Ph C Ph (B) HO (CH 2 )3
O
||
C CH 3
.
5161
O O

I.
|| ||
(C) CH 2OH C (CHOH)3 CH 2 OH (D) CH 2 (CH 2 ) 2 C CH 3

Q.64 Which of the following can be used for protection of carbonyl group

IE
(A) CH2OH–CH2OH / H- -
(B) CH2OH–CH2–CH2OH / H
-

(C) HS–(CH2)3–SH (D) CH2OH–CH2–CHO

.
-
:

←
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Q.65 Which of the following compound form stable hydrate on reaction with H2O ?
(A) H C H (B) Cl3C C H (C) Ninhydrin (D) Cyclopropanone

:
|| ||
O O

Q.66 Which of the following reaction does not represent correct major product?

(A) H3C – CH = O + H 2 C PPh 3 H3C – CH = CH2 + O = PPh3

(B) Ph CH HCN / C N
Ph CH CN
|| |
O OH
O Ph
OH
( i ) PhMgBr
(C) ( ii ) H 2O

(D) O + NH2 – OH O–NH2

Q.67 Which of the following compound form geometrically isomeric oxime on reaction with NH2– OH ?
O O
(A) (B) Ph – CH = O (C) (D) Ph C CH 3
||
O

Q.68 Which one of the following compounds will not give aldol reaction :
(A)Acetaldehyde (B) Formaldehyde (C) Pivaldehyde (D) Crotonaldehyde

Q.69 M ixture of Ph–CHO & HCHO is treated with NaOH then Cannizzaro reaction involves:
(A ) Oxidation of HCHO (B) Reduction of HCHO
(C) Oxidation of Ph–CHO (D) Reduction of Ph–CHO

Q.70 Which of thefollowing will form in thefollowing reaction?

O O
|| || Base
C6 H 5 C H + CH 3 C CH 3 products
( excess )

O O
|| ||
(A) C6H5 – CH = CH C CH 3 (B) C6H5 – CH = CH C CH = CH – C6H5
CH2
(C) C 6 H 5 C — C (D) CH 3 C CH C 6 H 5
|| CH3 |
O CH 3

Q.71 Knoevenagel reaction is catalysed by :

(A) NaOH (B) NH3 (C) EtOk (D) Pyridine

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Q.72 In the reaction sequence:

:
(i ) PCl5
C6 H 5 C CH 3 NH 2OH / H
[X] [Y]
|| (ii ) H 2O
O
[Y] will be:
O O
|| ||
(A) C6 H 5 C NHCH 3 (B) CH 3 C NH C 6 H 5

O
||
(C) C 6 H 5 CH 2 C NH 2 (D) C6H5CH2CN

Q.73 What will the product in following sequence?

(i ) ( CH 3 ) 2 NH Hydrolysis
CH2 = O + CH2 (COOC2H5)2 (P) Q R
(ii ) H 2 O

COOC2H5 COOH
(A) P is CH2= C (B) Q is CH2= C
COOC2H5 COOH
(C) R is CH2 = CH – COOH (D) R is CH2 = CH2
Q.74 Which of the following reactions can be named as reformastsky reaction?
O OH
||
(i ) Zn / ether
(A) C6 H 5 C C6 H 5 + BrCH2 – COOC2H5 C6H5 – C – CH 2 – COOC 2H 5
(ii ) H3O
C6H5

O
||
(B) H C C CH Cl OH CH 3 CH 2 C O ¯
3 2
||
O
O O OH O
|| || | ||
(i ) Zn / ether
(C) Ph C H + Br CH 2 C OEt Ph CH CH 2 C OEt
(ii ) H3O

O OH
|| |
(D) Ph C H ( i ) RMgBr / ether
Ph CH R
( ii ) H 3O

Q.75 What will be the product(s) of following reaction ?

O
14 Cl
( i ) OH
Products
(ii ) H 2O
O
O
14 C–OH 14 COOH 14
14 OH
(A) (B) (C) (D)

COOH
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 CARBONYL COMPOUND

Q.76 Which of the following alcohols can be oxidised by K2CrO4?

(A) Ethanol (B) Tert butyl alcohol
(C) Isopropyl alcohol (D)Allyl alcohol
Q.77 Choose the incorrect options ?
(A) Carbonyl compounds have lower boiling point than corresponding hydrocarbons & ethers
(B) Boiling point of carbonyl compounds are higher than that of ethers due to H-bonding
(C) Boiling point of carbonyl compounds are affected by molecular association & dipole-dipole
interactions
(D) Except methanal, all carbonyl compounds are solid or liquid at room temperature
Q.78 Which compound (s) are used in the preparation of perfumes & flavouring agents ?
(A) CH3–CH2–CHO (B) CH 3 CH 2 C CH 3
||
O
(C) C6H5CHO (D) None of these
Q.79 Which of the following reactions represent correct major product?
(i) DIBALH H3C–CH2–C–NH2
(A) H3C–CH2–C N (ii) H2O
O
(i ) DIBALH
(B) CH 3 C OCH 3 CH 3 C H
|| (ii ) H 2O ||
O O
H H
N O N
LAH
(C)
O O
Cl O
LiAlH 3
(D)
O OH
Q.80 In which of the following reactions product will be aldehyde?
( i ) O3 CO / H 2 / CO 2 ( CO )8
(A) CH 3 C C C2 H 5 (B) CH3–CH=CH2
| | ( ii ) H 2O
CH 3 CH 3
B2 H 6 HOH / HgSO 4 / H 2SO 4
(C) CH3–C CH (D) CH3–C CH
NaOH , H 2O 2

Q.81 Asparmate, an artificial sweetener is a peptide and has the following structure. Which of the following is
correct about the molecule?

(A) It has four functional groups

(B) It has three functional groups
(C) on hydrolysis it produces only one amino acid
(D) on hydrolysis it produces a mixture of amino acids
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 CARBONYL COMPOUND

Q.82 Which of the following reaction do(es) not represent correct major product ?

(A) C – Cl + (CH3)2Cd C – CH3

O O
O OH
|| |
(B) H 2C CH C CH 3 C N / HCN
H 2C CH C CH 3
|
CN
OH /
(C) H O¯ +
O O OH
+ H / H 2O
(D) N=O O
O¯
Q.83 Two isomeric ketones, 3-pentanone and 2-pentanone can be distinguished by :
(A) I2 / NaOH (B) NaSO3H (C) NaCN / HCl (D) 2,4-DNP
Q.84 Silver mirror test with Tollens reagent is given by :
(A) C6H5CHO (B) Ph–NH–OH
C6 H 5 CH 2 C CH 2OH
(C) || (D) CH3CHO
O
Q.85 Which of the following compound will give positive Tollens test

(A) CH3CHO (B)

(C) CH 3CH 2CH 2 CH 2CH OCH 3 (D)

|
OH
Q.86 Fehling solution gives red precipitate with:
(A)Aromatic aldehyde (B)Aliphatic aldehyde
(C) Ketones (D) -hydroxy ketones
Q.87 Which aldehydes & ketones are known for their odours & flavoures
(A)Vanillin (B)Acetophenone (C) Butyraldehyde (D) Camphor
[REASONING TYPE]
Q.88 Statement-1 : Benzaldehyde with HCN gives two isomeric compounds
Statement-2: Both nitrile and isonitrile compounds are possible when HCN reacts with carbonyl group.
(A) Statement-1 is true, statement-2 is true and statement-2 is correct explanation for statement-1.
(B) Statement-1 is true, statement-2 is true and statement-2 is NOT the correct explanation for statement-1.
(C) Statement-1 is false, statement-2 is true.
(D) Statement-1 is true, statement-2 is false.

Q.89 Statement-1 : The lower & higher members of aldehydes & ketones are dissolved in water.
Statement-2 : Aldehyde & ketones can form hydrogen bonds
(A) Statement-1 is true, statement-2 is true and statement-2 is correct explanation for statement-1.
(B) Statement-1 is true, statement-2 is true and statement-2 is NOT the correct explanation for statement-1.
(C) Statement-1 is true, statement-2 is false.
(D) Statement-1 is false, statement-2 is true.
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 CARBONYL COMPOUND

[PARAGRAPH TYPE]

Paragraph for question nos. 90 to 92

Aldehydes and ketones are especially susceptible to nucleophilic addition reaction because they have a
polar C = O group. The polarity of C = O group arises due to electronegativity difference
between carbon and oxygen.
+ –
C=O
Positive charge on carbon makes it reactive towards the nucleophile. This addition is catalysed by acid.

Reactivity of carbonyl compound towards nucleophilic addition increases with increase in the electron
deficiency at carbonyl carbon. Thus, (–I) groups increase while (+I) groups decrease the reactivity of
carbonyl compounds.
Q.90 Which among the following is most reactive towards nucleophilic addition reaction?
(A) FCH2CHO (B) ClCH2CHO (C) BrCH2CHO (D) ICH2CHO

Q.91 Carbonyl compounds show nucleophilic addition reaction with

(A) HCN (B) NaHSO3 (C) CH3MgCl (D)All of these

Q.92 Which of the following compound can not form stable hydrate on nucleophilic addition of H2O?
(A) Chloral (B) Ninhydrin (C) Cyclohexanone (D) Formaldehyde

Paragraph for question nos. 93 & 94

Oximes can be prepared by reaction of carbonyl compound with NH2OH
C = O + H2N – OH H 2O
C = N–OH
(Oximes)
If atoms or groups attached with double bonded C are different then geometrically isomeric oxime will
form.

Q.93 Which of the following carbonyl compound can form geometrically isomeric oxime on reaction with
NH2–OH ?
(A)Acetone (B) Cyclohexanone (C)Acetophenone (D) Benzophenone

3H 2O
Q.94 H C C C H + 3NH2 – OH Oximes
|| || | |
O O O
How many geometrical isomeric oxime will form in above reaction ?
(A) 4 (B) 3 (C) 5 (D) 6
[MATRIX TYPE]
Q.95 Column-I Column-II
(A) Methanal (P) Volatileliquid
(B) Ethanal (Q) Gas
(C) Aldehyde & ketones
other than formaldehyde (R) Liquid or solid

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 CARBONYL COMPOUND

Q.96 Match List-I with List-II and select the correct answer using the codes given below the lists.
List-I (Compound) List-II (Used as)
O
||
(A) 1,4 addition (P) Ph CH 2 C CH CH 2
(B) Tautomerism (Q) PCC

(C) Allylicbromination (R)

(D) Preparation of Ketone from 2° alcohol (S) NBS

Q.97 Column-I and column-II contains four entries each. Entries of column-I are to be matched with some
entries of column-II. One or more than one entries of column-Imayhave the matchingwith the same entries
of column-IIand one entryof column-Imayhave one or more than one matching with entries of column-II.
Column I Column II
(Reaction) (Type of intermediate formed)
HO
(A) Ph–CHCl2 (A) (P) Carbocation

Na
(B) R–Br dry ether
(Q) Carbanion

O
|| ( i ) Mg / H 2O
(C) CH 3 C CH 3 (R) Free – radical
(ii ) H 2SO 4 ,

H
(D) (S) Carbene

Q.98 Match list-I with list-II and select the correct answer using the codes give below the lists:
List-I List-II
LiAlH4
(A) CH2=CH–CHO (P) Acetal
H
(B) C6H5CHO + Ph–NH2 (Q) Schiff's base
(C) C6H5COCH3+CH3–CH2–NH2 H (R) Unsaturated alcohol
H
(D) RCHO + 2RCH2OH (S) Imine

Q.99 Column-I Column-II

(A) Formaldehyde (P) Preparation of acetic acid
(B) Acetaldehyde (Q) Used in Perfurmery & dye industries
(C) Benzaldehyde (R) Preparation of urea-formaldehyde glues
(D) Butanone (S) Preparation of vinyl acetate
(E) Propanaldehyde (T) Preparation of ethyl acetate

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 CARBONYL COMPOUND

ANSWER KEY
EXERCISE-1
O
O
|| C–H
Q.3 (a) CH3 CH 2 C H (b)

O O
Q.4 (A) (B)
Cl H
O
Q.5 (a) C

CH3

(b) H—C O
Et
OH O
Q.6 (A) (B)

Q.7 (a) 3>2>1>4

OH OH
| |
(b) (i) (CH 3 ) 2 CCN C H
(ii) 6 5 CCN
|
CH 3

Q.8 (a) (b)

R R O
HO—CH2
Q.9 Protection Glycol C=O + C cyclic-acetal
H HO—CH 2 H O
Glycol is used for protection of aldehyde and Ketone.
O
O
CH2–OH OH
O CH2–OH
C—H H
O LiAlH 4 O
CH H 3O
O C—H

Q.10 (a) (X) (Y) (b)

O
||
Q.11 (a) C C C C OH (b) CH 3 CH 2 CH 2 CH C CH 2 CH 3
|
CHO
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 CARBONYL COMPOUND

OH
|
(c) C–C–C–C=N–OH (d) C C C C Ph (e) Ph CH C CH 2 CH 3
|
OH CHO
|
(f) C C C CH C CH (g) C–C–C–C (h) C–C–C–C
OH OH
(i) (j) CN (k) OH
OH
|
CH 3 CH 2 CH 2 CH CH CO 2 H
(l) |
Et
Q.12 H /Br2 ; H2 / Ni ; NaOH

O
CO2H
NH NH2
Q.14 (A) (B) (C) (D) (E)
CO2H O
COOK

Q.15 (a) (i) CH3MgX / H+ (ii) Red Cu tube (iii) H2 / Ni (b) CH3MgBr / H+,
Q.17 4 Q.18 5
Q.19 (a) CH3–CH2–CH2–OH (b) CH3–CH2–CH2–OH
OH
|
(c) CH3–CH2–CH2–OH (d) CH 3 CH 2 CH CH 3
OH OH
| |
(e) CH 3 CH 2 CH C CH (f) CH 3 CH 2 CH Ph

(g) CH 3 CH 2 CH OCH3 (h) CH3 – CH2 – CH

|
OCH3
(i) CH3–CH2–CH=NH–PH (j) CH 3 CH 2 CH N CH 3 (Enamine)
|
CH 3
(k) CH3–CH2–CH=N–OH (l) CH3–CH2–CH=N–NH2
(m) CH3–CH2–CO2H (n) p-Nitro phenyl hydrazone
(o) semi carbazane (p) CH3– CH2–CH=CH–CH3
OH
|
(q) CH CH CH CN
3 2

Q.20 (a) (i) KMnO4, (ii) CH 2 OH , (iii) LiAlH4, (iv) H3O

|
CH 2 OH

(b) (i) CH 2 OH , (ii) NaBH4, (iii) H3O+, (c) (i) CH 2 OH , (ii) PH3P=CH–Et
| |
CH 2 OH CH 2 OH
(d) (i) H2, (ii) Ni ; (e) (i) H2, (ii) Pd–C ; (f) NaBH4
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 CARBONYL COMPOUND

EXERCISE-2
Q.1 C Q.2 C Q.3 C Q.4 D Q.5 B Q.6 C Q.7 A
Q.8 B Q.9 B Q.10 B Q.11 A Q.12 A Q.13 C Q.14 D
Q.15 D Q.16 C Q.17 B Q.18 C Q.19 A Q.20 A Q.21 B
Q.22 C Q.23 D Q.24 A Q.25 C Q.26 D Q.27 C Q.28 C
Q.29 C Q.30 A Q.31 C Q.32 C Q.33 B Q.34 B Q.35 B
Q.36 B Q.37 A Q.38 B Q.39 C Q.40 D Q.41 C Q.42 C
Q.43 B Q.44 D Q.45 C Q.46 B Q.47 D Q.48 C Q.49 C
Q.50 B Q.51 C Q.52 B Q.53 D Q.54 B Q.55 A Q.56 C
Q.57 A Q.58 CD Q.59 ABCD Q.60 ABC Q.61 ACD Q.62 AB Q.63 BC
Q.64 ABC Q.65 ABCD Q.66 ABC Q.67 BD Q.68 BC Q.69 AD Q.70 AB
Q.71 BD Q.72 AB Q.73 ABC Q.74 AC Q.75 BC Q.76 ACD Q.77 ABD
Q.78 ABC Q.79 BC Q.80 BC Q.81 AD Q.82 B Q.83 AB
Q.84 ABCD Q.85 ABC Q.86 BD Q.87 ABCD Q.88 D Q.89 D Q.90 A
Q.91 D Q.92 C Q.93 C Q.94 A Q.95 (A) Q (B) P (C) R
Q.96 (A) P, R, (B) P, (C) S, (D) Q,S Q.97 (A) Q,S, (B) Q, R, (C) P,R (D) P
Q.98 (A) R, (B) QS, (C) QS, (D) P Q.99 (A) R (B) PST (C) Q (D) Q (E) Q
EXERCISE-3
SECTION-A
Q.1 C Q.2 (CH2)6N4
O
|| CH3MgBr PCC
Q.3 H C H CH3–CH2–OH CH3–CHO Q.4 C
H3O

O OH OH
|| | |
H
Q.5 CH 3 C CH 3 HCN
CH 3 C CN CH 3 C COOH
H 2O |
|
CH 3 CH 3
( D)

Br CH 3 CH 3 CH 3
| | | |
C = CH 3 C COOH , B = CH 3 CH COOH , A = CH 3 C CH CH CH 3
|
CH 3
Q.6 C Q.7 B Q.8 A Q.9 AB Q.10 ABD
aq OH ¯
Q.11 CCl3–CHO HCOO + CHCl3 Q.12 C
Q.13 III > I > II > IV Q.14
CH 3 CH CH CH 2 CH 3
|
CHO
Q.15 Hydrazine form salt therefore no further reaction with aldehyde & ketones.

C – H + CH 3–CHO
Q.16 Q.17
O
Q.18 C
Q.19 (i) Tollen's reagent (ii) Benzo chloride is obtained
Q.20 AB

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