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Question

Which of the following reaction do not present in the major product of the given Birch reductions
990237_fe89e934d04d47c1b2da97b3b9242c1c.png

A
(i), (iii), (vi)
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B
(iv), (vi), (vii)
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C
(iv), (v), (vi)
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D
(i), (ii), (v), (vii)
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Solution

The correct option is D (iv), (vi), (vii)

As refer to the IMAGE 01, in Brich reduction, the benzene is converted to a diene and occurs through carbanion and free radical mechanism.

Since, it is an electron withdrawing group. Double bond is not attached with the group. Na in liquid NH3 is a reducing agent which converts triple bond into trans double bonds.

As refer to the IMAGE 02 due to the conjugation, only one double bond is lost.


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