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VITEEE 2013 Paper
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© examsnet.com
Question : 70
Total: 120
An organic compound B is formed by the reaction of ethyl magnesium iodide with a substance A, followed by treatment with dilute aqueous acid, Compound B does not react with PCC or PDC in dichloromethane. Which of the following is a possible compound for A ?
C
H
2
−
O
|
|
C
H
2
C
H
3
C
H
2
−
O
|
|
C
C
H
3
C
H
3
−
O
|
|
C
H
H
2
C
= 0
Validate
Solution:
B is a tertiary alcohol based on given properties.
(a)
C
H
2
−
C
H
2
+
C
H
3
C
H
2
MgI
H
3
O
+
→
C
H
3
C
H
2
C
H
2
C
H
2
O
H
1
°
‌
alcohol
(b)
C
H
3
C
H
2
O
|
|
C
C
H
3
+
C
H
3
C
H
2
MgI
H
3
O
+
→
C
H
3
C
H
2
O
H
|
C
|
C
H
3
H
C
H
2
C
H
3
3
°
‌
alcohol
(c)
C
H
3
C
H
O
+
C
H
3
C
H
2
M
g
I
H
3
O
+
→
C
H
3
C
|
O
H
C
H
2
C
H
3
2
°
‌
alcohol
(d) HCHO +
C
H
3
C
H
2
M
g
I
H
3
O
+
→
C
H
3
C
H
2
C
H
2
O
H
1
°
‌
alcohol
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