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NEET CHEMISTRYAminesMedium

Question

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).

Exam Context & Concepts Covered

This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Amines. Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.

CHEMISTRYAminespropanoicseriesreactionschchcoohxrightarrowsocl

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