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Propanoic acid gives a series of reactions as given below. CH3CH2COOHSOCl2BNH3CBr2/KOHDCH_3CH_2COOH \xrightarrow{SOCl_2} B \xrightarrow{NH_3} C \xrightarrow{Br_2/KOH} D The structure of D would be:

A

CH3CH2CH2NH2CH_3CH_2CH_2NH_2

B

CH3CH2CONH2CH_3CH_2CONH_2

C

CH3CH2NHCH3CH_3CH_2NHCH_3

D

CH3CH2NH2CH_3CH_2NH_2

Step-by-Step Solution

The given sequence of reactions is as follows:

  1. Formation of Acid Chloride (B): Propanoic acid (CH3CH2COOHCH_3CH_2COOH) reacts with thionyl chloride (SOCl2SOCl_2) to form propanoyl chloride (BB). CH3CH2COOH+SOCl2CH3CH2COCl(B)+SO2+HClCH_3CH_2COOH + SOCl_2 \longrightarrow CH_3CH_2COCl (B) + SO_2 + HCl

  2. Formation of Amide (C): Propanoyl chloride (BB) reacts with ammonia (NH3NH_3) to undergo nucleophilic acyl substitution, forming propanamide (CC). CH3CH2COCl+2NH3CH3CH2CONH2(C)+NH4ClCH_3CH_2COCl + 2NH_3 \longrightarrow CH_3CH_2CONH_2 (C) + NH_4Cl

  3. Hofmann Bromamide Degradation (D): Propanamide (CC) reacts with bromine (Br2Br_2) in the presence of a strong base like potassium hydroxide (KOHKOH). This is the Hofmann bromamide degradation reaction, which converts a primary amide to a primary amine with one carbon atom less than the original amide. CH3CH2CONH2+Br2+4KOHCH3CH2NH2(D)+K2CO3+2KBr+2H2OCH_3CH_2CONH_2 + Br_2 + 4KOH \longrightarrow CH_3CH_2NH_2 (D) + K_2CO_3 + 2KBr + 2H_2O

Therefore, the final product D is ethanamine (CH3CH2NH2CH_3CH_2NH_2).

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