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Identify Major Product in Organic Reaction Sequence Starting from Propanoic Acid

Consider the following organic reaction sequence. Choose the final product (X)(X) from the following (consider the major product in all intermediate reactions)

Question Diagram 1

Options

A

Benzene

Correct
B

Phenol

C

Propanol

D

Chlorobenzene

Topics & Concepts

Step-by-Step Solution

To determine the final major product (X)(X) of the given organic reaction sequence, we analyze each reaction step-by-step:

Step 1: Reaction of Propanoic Acid with NH3/Δ\text{NH}_3 / \Delta

Propanoic acid (CH3CH2COOH\text{CH}_3\text{CH}_2\text{COOH}) reacts with ammonia (NH3\text{NH}_3) upon heating to form an ammonium salt which, on thermal dehydration, yields propanamide: CH3CH2COOHNH3,ΔCH3CH2CONH2+H2O\text{CH}_3\text{CH}_2\text{COOH} \xrightarrow{\text{NH}_3, \Delta} \text{CH}_3\text{CH}_2\text{CONH}_2 + \text{H}_2\text{O}


Step 2: Hofmann Bromamide Degradation (NaOH/Br2\text{NaOH}/\text{Br}_2)

Propanamide (CH3CH2CONH2\text{CH}_3\text{CH}_2\text{CONH}_2) undergoes the Hofmann bromamide reaction on treatment with Br2\text{Br}_2 and aqueous NaOH\text{NaOH}, resulting in the loss of the carbonyl carbon to produce a primary amine with one carbon less, which is ethylamine (ethanamine): CH3CH2CONH2+Br2+4NaOHCH3CH2NH2+Na2CO3+2NaBr+2H2O\text{CH}_3\text{CH}_2\text{CONH}_2 + \text{Br}_2 + 4\text{NaOH} \rightarrow \text{CH}_3\text{CH}_2\text{NH}_2 + \text{Na}_2\text{CO}_3 + 2\text{NaBr} + 2\text{H}_2\text{O}


Step 3: Reaction with Nitrous Acid (HNO2/H2O,0C\text{HNO}_2/\text{H}_2\text{O}, 0^\circ\text{C})

When ethylamine (CH3CH2NH2\text{CH}_3\text{CH}_2\text{NH}_2) reacts with nitrous acid (HNO2\text{HNO}_2) at 0C0^\circ\text{C}, an unstable aliphatic diazonium salt (CH3CH2N2+Cl\text{CH}_3\text{CH}_2\text{N}_2^+\text{Cl}^-) is formed. This salt rapidly decomposes in aqueous medium with the release of N2\text{N}_2 gas to form ethanol: CH3CH2NH2HNO2/H2O,0CCH3CH2OH+N2+HCl\text{CH}_3\text{CH}_2\text{NH}_2 \xrightarrow{\text{HNO}_2 / \text{H}_2\text{O}, 0^\circ\text{C}} \text{CH}_3\text{CH}_2\text{OH} + \text{N}_2\uparrow + \text{HCl}


Step 4: Reaction with Benzenediazonium Chloride (C6H5N2Cl,0C\text{C}_6\text{H}_5\text{N}_2\text{Cl}, 0^\circ\text{C})

Ethanol (CH3CH2OH\text{CH}_3\text{CH}_2\text{OH}) acts as a mild reducing agent. When treated with benzenediazonium chloride (C6H5N2Cl\text{C}_6\text{H}_5\text{N}_2\text{Cl}), ethanol reduces the diazonium group to form benzene (C6H6\text{C}_6\text{H}_6), while ethanol itself gets oxidized to ethanal (CH3CHO\text{CH}_3\text{CHO}): C6H5N2Cl+CH3CH2OHC6H6+N2+HCl+CH3CHO\text{C}_6\text{H}_5\text{N}_2\text{Cl} + \text{CH}_3\text{CH}_2\text{OH} \rightarrow \text{C}_6\text{H}_6 + \text{N}_2\uparrow + \text{HCl} + \text{CH}_3\text{CHO}

Thus, the final major product (X)(X) is Benzene.

Correct Option: A (Benzene)

Identify Major Product in Organic Reaction Sequence Starting from Propanoic Acid | Chemistry PYQ Solution - JEE Challenger