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Aldehyde and Ketone (DPP)
Aldehyde and Ketone (DPP)
Exercise:1
Q. 1
Q.2
Q.3
Q.4
Q.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: [IIT 1993]
(A) CH3CH2CHO
(B) CH3COCH3
(C) CH2= CHCH2OH
(D) CH2= CH O CH3
Q.6
Under Wolff Kishner reduction conditions, the conversions which may be brought about is?
[IIT 1995]
(A) Benzaldehyde into Benzyl alcohol
(B) Cyclohexanol into Cyclohexane
(C) Cyclohexanone into Cyclohexanol
(D) Benzophenone into Diphenylmethane
Q.7
In the reaction, P is
N
.J
.S
IR
[IIT 1990]
[IIT 1995]
CH3
CO
SeO2
P + Se + H2O
CH3
(A) CH3COCHO
(C) CH3COCH2OH
(B) CH3COOCH3
(D) None
OH
Q.9
Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group is[IIT 1997]
(A) MeCOCl
(B) MeCHO
(C) MeCOOMe
(D) MeCOOCOMe
Q.10
In a Cannizzaro reaction the intermediate which is the best hydride donor is:
[IIT 1997]
H
H
IR
Q.8
(A) C6H5 C O
(B) C6H5 C O
N
.J
.S
OH
(C)
O2N
(D)
O
O
CH3O
Q.11
Q.12
Among the following compounds, which will react acetone to give a product containing > C = N
(A) C6H5NH2
(B) (CH3)3N
[IIT 1998]
(C) C6H5NHC6H5
(D) C6H5NHNH2
Q.13
(B) CH3CH2CH2CHO
[IIT 1998]
Q.14
[IIT 1998]
Q.15
[IIT 1998]
Q.16
Q.17
[IIT 2000]
Q.18
[IIT 2000]
CH2CH3
HO
HO
IR
CH3
(D) NaBH4
A mixture of benzaldehyde and formaldehyde on heating with aqueous NaOH solution gives:
[IIT 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
Q.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.
[IIT 2002]
(A) CH3CH2CH= NNHCONH2
(B) CH3 C = NNHCONH2
N
.J
.S
Q.19
CH3
(C)
CH3 C = NCONHNH2
CH3
Q.21
Q.22
[IIT 2003]
(ii) H /H2O
CHO OHC
COOH
HOOC
CH2OH
CH2OH
(A)
(B)
COOH
CH2OH
HOOC
COOH
CH2OH
(C)
(D)
COOH
CH2OH
CH2OH
O
O
OCOCH3
Acidic
Products formed by P & Q can be differentiated by :
IR
Q.23
OCOCH3 Hydrolysis
Q
N
.J
.S
Q.24
[IIT 2003]
(A) 2,4 DNP
(B) Lucas reagent (ZnCl2) conc. HCl
(C) NaHSO3
(D) Fehlings solution
The order of reactivity of phenyl Magnesium Bromide with the following compounds is :
[IIT 2004]
O
H3C
CH3
(I)
H3C
Ph
(II)
Ph
(III)
Q.25
CHO
CH3COONa
+ X
MeO
What is X?
(A) CH3COOH
[IIT 2005]
MeO
(C) (CH3CO)2O
Q.26
The smallest ketone and its next homologue are reacted with NH2OH to form oxime.
(A) Two different oximes are formed
(B) Three different oximes are formed
(C) Two oximes are optically active
(D) All oximes are optically active
[JEE 2006]
Q.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:
[JEE 2007]
(A)
CHO (C)
CO2H
COOH (D)
CO2H
IR
Q.28
CHO (B)
O Na
N
.J
.S
OH
CHO
(I)
(Intermediate)
Q.29
Q.30
Q.31
aq. HCl
CH3
CH3
CHO
CH3
(I)
(III)
(II)
Which one of the following reagents is used in the above reaction? [JEE 2007]
(A) aq.NaOH + CH3Cl
(B) aq. NaOH +CH2Cl2
(C) aq. NaOH + CHCl3
(D) aq. NaOH + CCl4
[JEE 2007]
(B) +CHCl2
(D) : CCl3
O Na
(A)
CH3
CH2OH
CCl3
(C)
CH3
O Na
O Na
CHCl2
(B)
O Na
CH2Cl
[JEE 2007]
(D)
CH3
CH3
Q.32
Match the compounds/ion in column-I with their properties/reaction in Column- II. Indicate your answer
by darkening the appropriate bubbles of the 4 4 matrix given in the ORS.
[JEE 2007]
Column-I
(A) C6H5CHO
Column-II
(P) gives precipitate with
2,4- dinitrophenylhydrazine
(Q) gives precipitate with AgNO3
(R) is a nucleophile
(S) is involved in cyanohydrin formation
(B) CH3C CH
(C) CN
(D) I
IR
Q.33
N
.J
.S
In the following reaction sequence, products I, J and L are formed. K represents a reagent.
1. Mg / ether
Cl
. NaBH 4
2. CO2
K
H2
Hex-3-ynal 1
J Me
2. PBr3
Pd / BaSO 4
3. H3O
O
quinoline
[JEE 2008]
Me
Q.34
(A) Me
Br
(B)
(C) Me
Br
(D) Me
(B) Me
Br
Br
[JEE 2008]
O & SO2Cl2
Me
(C)
Q.35
CHO
[JEE 2008]
(B) Me
CHO
(D) Me
CHO
CHO
(C) Me
Q.36
CH3
Ph
+ PhMgBr
[JEE 2008]
O
(C)
Q.37
Ph
O
H
+ PhCH2 MgBr
(D)
Ph
Me
Ph
CH3
(A)
H3C
Ph
Ph
MgBr
[JEE 2008]
(B)
Ph
Ph
CH3
(C)
H3C
CH3
(D)
Q.38
+ PhCH2MgBr
N
.J
.S
(C)
CH3
Ph
IR
Ph
CH2Ph
Ph
[JEE 2008]
1. O 3
. MeMgBr
1. OH
P 1
Q
R
S
2. Zn,H2O
2. H , H2O
3. H2SO 4 ,
Q.39
[JEE 2009]
Me
(B)
Me
O
O
(C)
Me
(D)
Me
IR
Et
Q.40
2.
(A)
[JEE 2009]
H
COMe
Me
N
.J
.S
Me
Me Me
(B)
H
COMe
Me
Me
Me Me
H
CHO
(C)
Me
Et
Me Et
O
Me
CH3
CHO
(D)
Me
Me Et
Q.41
[JEE 2009]
(A)
(B)
Me
Me
O
Me
Me
(C)
(D)
Me
Me
EXERCISE-2
NaOC 2H5
C6H5 CHO + CH3 COOC2H5
(D).
[IIT 1995]
CH3CH2
Q.2
(i) KCN/H2SO4
C=O
(ii) LiAlH4
IR
Q.1
[IIT 1996]
Acetophenone on reaction with hydroxylamine- hydrochloride can produce two isomeric oximes. Write
structure of the oximes.
[IIT 1997]
Q.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).
[IIT 1998]
O
O
CHC6H5
N
.J
.S
Q.3
(C)
Q.5
Q.6
(i)LiAlH
(D)
(ii) H ,heat
[IIT 1998]
[IIT 2000]
Base
Q.7
[IIT 2000]
Q.8
Five isomeric para-disubstituted aromatic compounds A to E with molecular formula C8H8O2 were
given for identification. Based 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
(ii) C gives positive iodoform test.
(iii)D is readily extracted in aqueous NaHCO3solution.
9
[IIT 2002]
Cl
HCl
+
CH2= CHCH2O Na
C6H12
HCl
HNO3/ H2SO4
H2/ Pd/C
C6H13Cl + (C)
(B)
(D)
ozonolysis
IR
Q.10
Na-Hg
CH2CH2CH3
(E)
Q.11
N
.J
.S
ozonolysis
NaOH
(A)
(F) + (G)
NCOONa + 1alcohol
(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.
[IIT 2003]
CH2OH
CH2OH
HO
(A)
OH H
OH
OH
(B)
OH
HO
CH2OH
HOH2C
O HO
[IIT 2005]
OH
OH H
HO
OH H
(Q)
(P)
EXERCISE-1
Q.No.
Ans.
Q.No.
Ans.
Q.No.
Ans.
Q.No.
Ans.
Q.No.
Ans.
1
B
11
B
21
C
31
B
37
A
2
A
12
A,D
22
C
32
38
D
3
D
13
A
23
D
A
P, S
39
B
4
B
14
A,B,D
24
C
B
Q
40
A
5
D
15
B
25
C
C
Q,R, S
41
B
6
D
16
B, D
26
B
D
Q,R
7
A
17
B
27
A
33
D
8
B
18
B
28
C
34
A
9
A
19
A
29
C
35
C
10
D
20
A
30
C
36
B
EXERCISE-2
10
CH3CH2
Q. 1
OH
C
C6H5CH = CHCOOC2H5
Q.2
(D)
CH2NH2
(a racemic mixture)
C6H5 C CH3
N OH
C6H5 C CH3
and
HO N
syn
anti (isomers)
IR
Q.3
CH= CH C C CHO
CHO CHO
+2
COOH
Ozonolysis
Q.4
(A)
COOH
(B)
CHC6H5
C6H5CHO
(Oxalic acid)
Base
Br
(D)
CH3
C CH3
Q.7
Ph
Ph
Q.6
+ Base
(C)
COOH
N
.J
.S
Q.5
Ag
CH3
COONa + CHBr3
Br2 + NaOH
CH3
(A)
(B)
(C)
CHO
Q.8
CHO
or
(A)
OCH3
CH2CHO
(B)
CH2OH
C CH3
(C)
OH
COOH
(D)
OH
O CH = CH2
(E)
CH3
OH
11
NO2
Q.9
(C)
(B)
(A)
Cl
Cl
Cl
Cl
Cl
Cl
NO2
NH2
Bu
Bu
(D)
(E)
Cl
Cl
O CH2 CH = CH2
Me3C CH = CH2
O Pr
IR
Q.10
Bu
Bu
C Pr
(A)
Cl
(C)
N
.J
.S
alc.KOH
(A)
Ozonolysis
NaOH
Q.11 In structure (P) both the rings are present in acetyl form therefore it will not hydrolyse in solution that's
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.
12