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Question

CH3CH2CCCH2CH3Nain−−−LiqNH3 Product (P).
P is:

A
n-hexene
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B
cis-2-hexene
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C
cis-3-hexene
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D
trans-3-hexene
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Solution

The correct option is D trans-3-hexene
The product P is trans-3-hexene. When 3-hexyne is reduced with Na in liq ammonia, trans-3-hexene is obtained. In this reaction, carbon carbon tripple bond is selectively reduced to C=C double bond. The alkene formed is trans alkene as the addition of molecule of hydrogen to carbon carbon tripple bond is trans.
CH3CH2CCCH2CH3Nain−−−LiqNH3cisCH3CH2C=CCH2CH3

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