On hydrolysis of a "compound", two compounds are obtained. One of which on treatment with sodium nitrite and hydrochloric acid gives a product which does not respond to iodoform test. The second one reduces Tollens reagent and Fehling's solution. The "compound" is
- CH3CH2CH2NC
- CH3CH2CH2CN
- CH3CH2CH2ON=O
- CH3CH2CH2CON(CH3)2
Answer
(1) CH3CH2CH2NC
Solution
Acid hydrolysis of propyl isocyanide:
CH3CH2CH2NC + 2H2O H+ CH3CH2CH2NH2 + HCOOH
(i) Propan-1-amine with NaNO2 + HCl (nitrous acid) gives propan-1-ol:
CH3CH2CH2NH2 + HNO2 CH3CH2CH2OH + N2 + H2O
⇒ propan-1-ol has no CH3CH(OH)- group ⇒ no iodoform test.
(ii) Methanoic acid (HCOOH) has an aldehydic H ⇒ reduces Tollens' reagent and Fehling's solution.
∴ The "compound" is CH3CH2CH2NC.
Answer: (1)