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Aldehydes, Ketones And Carboxylic Acids

Question
CBSEENCH12011388

In a set of reactions, propionic acid yielded a compound D.

CH subscript 3 CH subscript 2 COOH space rightwards arrow with SOCl subscript 2 on top space straight B space rightwards arrow with NH subscript 3 on top space straight C space rightwards arrow from Br subscript 2 to KOH of space straight D
The structure of D would be:

  • CH3CH2CH2NH2

  • CH3CH2CONH2

  • CH3CH2NHCH3

  • CH3CH2NH2

Solution

D.

CH3CH2NH2

For reaction,
stack CH subscript 3 CH subscript 2 COOH with apostrophe straight A apostrophe below space rightwards arrow from negative SO subscript 2 comma negative HCl to SOCl subscript 2 of space stack CH subscript 3 CH subscript 2 COCl with apostrophe straight B apostrophe below rightwards arrow from negative HCl to NH subscript 3 of space stack CH subscript 3 CH subscript 2 CONH subscript 2 with apostrophe straight C apostrophe below
rightwards arrow from plus thin space Br subscript 2 space left parenthesis negative 2 Kbr comma space minus space straight K subscript 2 CO subscript 3 right parenthesis comma negative 2 straight H subscript 2 straight O to 4 KOH of space space stack CH subscript 3 CH subscript 2 NH subscript 2 with apostrophe straight D apostrophe space left parenthesis ethyl space amine right parenthesis below
left parenthesis Hofmann minus Bromamide space reaction right parenthesis
Hence, compound 'D' is CH3-CH2-NH2