A student performed analysis of aliphatic organic compound X which on analysis gave C = 61.01%, H = 15.25%, N = 23.74%. This compound, on treatment with HNO2/H2O produced another compound Y which did not contain any nitrogen atom. However, the compound Y upon controlled oxidation produced another compound Z that responded to iodoform test. The structure of X is

Q. A student performed analysis of aliphatic organic compound ‘X’ which on analysis gave C = 61.01%, H = 15.25%, N = 23.74%. This compound, on treatment with HNO2/H2O produced another compound ‘Y’ which did not contain any nitrogen atom. However, the compound ‘Y’ upon controlled oxidation produced another compound ‘Z’ that responded to iodoform test.

The structure of ‘X’ is :

A. CH3–CH2CH(NH2)–CH3
B. CH3CH2CH2NH2
C. Ph–CH(CH3)–NH2
D. (CH3)2CH–NH2

Correct Answer: (CH3)2CH–NH2

Solution

From the given percentage composition:

C = 61.01%, H = 15.25%, N = 23.74%

These values correspond to the molecular formula:

C3H9N

The compound reacts with nitrous acid (HNO2/H2O) to give a compound Y without nitrogen, indicating that X is a primary aliphatic amine, which forms an alcohol on reaction with nitrous acid.

The alcohol Y on controlled oxidation gives a compound Z that responds to the iodoform test. Iodoform test is given by compounds containing:

–COCH3 or –CH(OH)CH3

Therefore, Y must be a secondary alcohol, and hence X must be isopropylamine.

Thus, the correct structure of X is:

(CH3)2CH–NH2

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