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NEET CHEMISTRYAlcohols, Phenols and EthersMedium

Question

The product 'D' in the following reaction is: CH3CNH3O+ANH3,ΔBNaOBrCNaNO2/HClDCH_3CN \xrightarrow{H_3O^+} A \xrightarrow{NH_3, \Delta} B \xrightarrow{NaOBr} C \xrightarrow{NaNO_2/HCl} D

A

HCHO

B

CH₃COOH

C

CH₃NH₂

D

CH₃OH

Step-by-Step Solution

The reaction sequence proceeds as follows:

  1. Hydrolysis (A): Methyl cyanide (CH3CNCH_3CN) undergoes acid hydrolysis (H3O+H_3O^+) to form Ethanoic acid (CH3COOHCH_3COOH) [A]. CH3CN+2H2O+H+CH3COOH+NH4+CH_3CN + 2H_2O + H^+ \rightarrow CH_3COOH + NH_4^+
  2. Amide Formation (B): Heating ethanoic acid with ammonia (NH3,ΔNH_3, \Delta) removes water to form Ethanamide (CH3CONH2CH_3CONH_2) [B]. CH3COOH+NH3CH3COONH4ΔCH3CONH2+H2OCH_3COOH + NH_3 \rightarrow CH_3COONH_4 \xrightarrow{\Delta} CH_3CONH_2 + H_2O
  3. Hoffmann Bromamide Degradation (C): Reaction with sodium hypobromite (NaOBrNaOBr or Br2/NaOHBr_2/NaOH) converts the amide to a primary amine with one less carbon atom. Thus, Methylamine (CH3NH2CH_3NH_2) [C] is formed. CH3CONH2+Br2+4NaOHCH3NH2+Na2CO3+2NaBr+2H2OCH_3CONH_2 + Br_2 + 4NaOH \rightarrow CH_3NH_2 + Na_2CO_3 + 2NaBr + 2H_2O
  4. Reaction with Nitrous Acid (D): Primary aliphatic amines react with nitrous acid (NaNO2+HClNaNO_2 + HCl) to form unstable diazonium salts which liberate nitrogen gas and form alcohols. Thus, Methanol (CH3OHCH_3OH) [D] is the final product. CH3NH2+HNO2[CH3N2+Cl]H2OCH3OH+N2+HClCH_3NH_2 + HNO_2 \rightarrow [CH_3N_2^+Cl^-] \xrightarrow{H_2O} CH_3OH + N_2 + HCl

Exam Context & Concepts Covered

This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Alcohols, Phenols and Ethers. 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.

CHEMISTRYAlcohols, Phenols and Ethersproductfollowingreactionxrightarrowhoxrightarrownh

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