Which one of the following compounds do not give a primary alcohol on reduction ?

Propanal

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Propanoic acid

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Methyl propanoate

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Propan-2-one

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Solution

The correct option is D Propan-2-one
Reduction product(s) of the given compounds are as follows
(a) $C H_{3} C H_{3} C H O P r o p a n a l L i A l H_{4} - --- \to 2 H C H_{3} C H_{2} C H_{2} O H P r o p a n o l (1^{o} a l c o h o l)$

(b) $C H_{3} C H_{3} C O O H P r o p a n o i c a c i d L i A l H_{4} - --- \to 4 H C H_{3} C H_{2} C H_{2} O H P r o p a n o l (1^{o} a l c o h o l)$

(c) $C H_{3} C H_{3} C O O H_{3} M e t h y l p r o p a n o a t e L i A l H_{4} - --- \to C H_{3} C H_{2} C H_{2} O H P r o p a n o l (1^{o} a l c o h o l) + C H_{3} O H M e t h a n o l (1^{o} a l c o h o l)$

(c) $C H_{3} - C | | O P r o p a n - 2 - o n e - C H_{3} L i A l H_{4} \to C H_{3} - C H | O H P r o p a n - 2 - o l (2^{o} a l c o h o l) - C H_{3}$

Thus, propan-2-one is the compound which on reduction does not produce $1^{o}$ alcohol.

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