Question

An organic compound when treated with nitrous acid, gave an alcohol and gas was evolved.

(1) On warming with and caustic potash gave (3) which on reduction gave isopropylmethylamine. Predict the structure of (1).

(1)

(2) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } - \mathrm { NH } - \mathrm { CH } _ { 3 }$

(3)

(4) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { NH } _ { 2 }$

• A. Compound 1 structure
• B. Compound 2 structure
• C. Compound 3 structure
• D. Compound 4 structure

Answer 1

Answer: (A)

Compound 1 structure

Answer 2

: As (1) gives alcohol on treatment with nitrous acid thus it should be primary amine. $\mathrm { C } _ { 3 } \mathrm { H } _ { 9 } \mathrm {~N}$ has two possible structure with $- \mathrm { NH } _ { 2 }$group.

$\mathrm { CH } _ { 3 } - \mathrm { CH } _ { 2 } - \mathrm { CH } _ { 2 } - \mathrm { NH } _ { 2 }$ or

As it gives isopropylmethyl amine thus it should be isopropyl amine non n-propylamine

$( A )$