Aliphatic Compounds Containing Nitrogen - Result Question 8

####8. A compound ’ X ’ on treatment with Br2/NaOH, provided C3H9N, which gives positive carbylamine test. Compound ’ X ’ is

(2019 Main, 11 Jan II)

(a) CH3COCH2NHCH3

(b) CH3CH2CH2CONH2

(c) CH3CON(CH3)2

(d) CH3CH2COCH2NH2

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Answer:

Correct Answer: 8. (b)

Solution:

  1. The molecular formula, C3H9N refers to four structural isomers of amines

(a) CH3CH2CH2NH2

(b) CH3CHCH3

(c)

CH3NHCH2CH3 Secondary amine 

(d)

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.

CH3CH2CH2|NH2Na2CO3Br2CH3CH2CH2NH2

So, ’ X ’ can be CH3CH2CH2CONH2 (a) or CH3CH(CONH2)CH3 (b).

Carbylamine test given by (a) and (b)

CH3CH2CH2NH2+CHCl3+3KOHΔ

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



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