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Question

A compound 'X' on treatement with Br2/NaOH provided C3H9N, which gives positive carbylamine test. Compound 'X' is:

A
CH3COCH2NHCH3
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B
CH3CH2CH2CONH2
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C
CH3CON(CH3)2
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D
CH3CH2COCH2NH2
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Solution

The correct option is B CH3CH2CH2CONH2
The molecular formula, C3H9N refers to four structural isomers of amines:

Here, only (a) and (b) (primary amines) can be prepared from their respective amides by Hoffmann bromamide (Br2/NaOH) method and can give positive carbylamine test.

So, 'X' can be CH3CH2CH2CONH2 (P)
or CH3CH(CONH2)CH3 (Q)
Carbylamine test given by (P) and (Q):

As (Q) is not among the given options So, it is ruled out and therefore compound (X) is CH3CH2CH2CONH2.

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