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IIT JEE Advanced 2009 Paper 1
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© examsnet.com
Question : 40
Total: 60
Match each of the compounds in Column I with its characteristic reaction(s) in Column II:
Column I
Column II
(A)
C
H
3
C
H
2
X
H
2
C
N
(P) Reduction with Pd -
C
l
2
(B)
C
H
3
C
H
2
O
C
O
C
H
3
(Q) Reduction with
S
n
C
l
2
/ HCl
(C)
C
H
3
−
C
H
=
C
H
−
C
H
2
O
H
(R) Development of foul smell on treatment with chloroform and alcoholic KOH
(D)
C
H
3
C
H
2
C
H
2
C
H
2
N
H
2
(S) Reduction with diisobutylaluminium hydride (DIBAL-H)
(T) Alkaline hydrolysis
(A)→(P), (R), (S), (T); (B)→(S), (T); (C)→(P); (D) →(P)
(A)→(P), (Q), (S), (T); (B)→(S), (T); (C)→(P); (D) →(R)
(A)→(P), (Q), (S), (T); (B)→(S), (T); (C)→(P); (D) →(S)
(A)→(P), (S), (T); (B)→(S), (T); (C)→(P); (D) →(R)
Validate
Solution:
(A)
C
H
3
C
H
2
C
H
2
C
N
P
d
−
C
∕
H
2
→
C
H
3
C
H
2
C
H
2
C
H
2
N
H
2
S
n
C
l
2
∕
H
C
l
→
C
H
3
C
H
2
C
H
2
C
H
=
N
H
.
H
C
l
D
I
B
A
L
−
H
→
C
H
3
C
H
2
C
H
2
C
H
2
N
H
2
Alkine
→
Hyrolysis
C
H
3
C
H
2
C
H
2
C
O
O
H
(B)
Reaction with DIBAL-H and alkaline hydrolysis:
C
H
5
−
O
|
|
C
−
O
C
2
H
5
D
I
B
A
L
−
H
→
C
H
3
−
O
|
|
C
−
H
+
C
2
H
5
O
H
C
H
5
−
O
|
|
C
−
O
C
2
H
5
O
H
−
→
C
H
3
C
O
O
−
+
C
2
H
5
H
(C) Reduction with
P
d
−
C
∕
H
2
:
C
H
3
−
C
H
=
C
H
−
C
H
2
O
H
P
d
−
C
∕
C
H
2
→
C
H
3
−
C
H
2
−
C
H
2
−
C
H
2
O
H
(D)
Foul smell on treatment with
C
H
C
l
3
+
K
O
H
:
R
N
H
2
C
H
C
l
3
+
K
O
H
→
R
N
C
Foul
smell
+
K
C
l
+
H
2
O
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