Which of the following reaction will not produce $1^{o}$ amine as major product?

H_{3} C - C H_{2} - C \equiv N \to (C o m p l e t e h y d r o l y s i s) H^{+} / H_{2} O

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H_{3} C - C H_{2} - O | | C - O H N_{3} H - -- \to H^{+}

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Phthalimide i . K O H - ------------- \to i i . C H_{3} - C H_{2} - C H_{2} - I O H^{-} / H_{2} O - ----- \to

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C H_{3} - C H_{2} - B r + N H_{3} (e x c e s s) \to

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Solution

The correct option is A $H_{3} C - C H_{2} - C \equiv N \to (C o m p l e t e h y d r o l y s i s) H^{+} / H_{2} O$
(a) Complete hydrolysis of nitrile gives carboxylic acid.
$H_{3} C - C H_{2} - C \equiv N H^{+} / H_{2} O - ---- \to H_{3} C - C H_{2} - C O O H$

(b) Schmidt Reaction:
$H_{3} C - C H_{2} - O | | C - O H N_{3} H - -- \to H^{+} H_{3} C - C H_{2} - N H_{2}$

(d) Gabriel Phthalimide Synthesis:
$Phthalimide i . K O H - ------------- \to i i . C H_{3} - C H_{2} - C H_{2} - I O H^{-} / H_{2} O - ----- \to C H_{3} - C H_{2} - C H_{2} - N H_{2}$

(d) $C H) 3 - C H_{2} - B r + N H_{3} (e x c e s s) \to E t - N H_{2}$

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