In the following sequence of reactions, the final product 'D' is :

$C H_{3} - C H = C H - C H_{2} - C H_{2} - C H_{2} - C O O H$

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$H_{3} C - C H = C H - C H (O H) - C H_{2} - C H_{2} - C H_{3}$

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Solution

The correct option is B

Terminal alkyne have acidic proton, hence, on reacting with $N a N H_{2}$ it form acetylide ion. It undergoes nucleophilic substitution reaction with alkyl halide to form compound (B). Here, acetylide ion act as a nucleophile.
Compound (B), alkyne on reacting with $H_{2}$ in presence of Pd undergoes hydrogenation to give alkane, compound (C).

$C r O_{3}$ oxidise secondary alcohol to ketone group.

Hence, option (a) is correct.

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