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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

1. CH3 CH2 CH2 CON(CH3)2
2. CH3 CH2 CH2 NC
3. CH3 CH2 CH2 CN
4. CH3 CH2 CH2 ON=O

Correct answer: CH3 CH2 CH2 CN

Solution

The compound CH3CH2CH2CN undergoes hydrolysis to form CH3CH2CH2COOH (propanoic acid) and NH3. Propanoic acid does not respond to the iodoform test, while NH3 does not reduce Tollens' reagent or Fehling's solution. Thus, the compound is CH3CH2CH2CN.

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