In the following sequence of reactions : Toluene →KMnO4A→SOCl2B→H2/PdBaSO4C the product C is :

In the following sequence of reactions : Toluene \overset{\left(KMnO\right)_{4}}{\rightarrow} A \overset{\left(SOCl\right)_{2}}{\rightarrow} B \underset{\left(BaSO\right)_{4}}{\overset{H_{2} / Pd}{\rightarrow}} C the product C is :

Engineering

Chemistry

Preparation of Aldehyde and Ketones

Reduction

Nucleophilic addition

Question

In the following sequence of reactions :

Toluene $\overset{{KMnO}_{4}}{\to} A \overset{{SOCl}_{2}}{\to} B \underset{{BaSO}_{4}}{\overset{H_{2} / Pd}{\to}} C$ the product C is :

C₆H₅CH₂OH

C₆H₅CH₃

C₆H₅CHO

C₆H₅COOH

This question involves a sequence of organic reactions starting from toluene. Let's analyze each step to identify the final product C.

Step 1: Oxidation of Toluene with KMnO₄

Toluene (C₆H₅CH₃) undergoes oxidation with potassium permanganate (KMnO₄). The alkyl side chain (methyl group) attached to the benzene ring is oxidized to a carboxylic acid group, regardless of the chain length (as long as it has a benzylic hydrogen).

Reaction: $C_{6} H_{5} C H_{3} \overset{{KMnO}_{4}}{\to} C_{6} H_{5} C O O H$

So, product A is Benzoic acid (C₆H₅COOH).

Step 2: Conversion to Acid Chloride with SOCl₂

Benzoic acid (A) reacts with thionyl chloride (SOCl₂). This reaction converts the carboxylic acid group (–COOH) into an acid chloride group (–COCl).

Reaction: $C_{6} H_{5} C O O H \overset{{SOCl}_{2}}{\to} C_{6} H_{5} C O C l$

So, product B is Benzoyl chloride (C₆H₅COCl).

Step 3: Rosenmund Reduction

Benzoyl chloride (B) undergoes reduction with hydrogen gas in the presence of a palladium catalyst poisoned with barium sulfate (H₂/Pd-BaSO₄). This specific reaction is known as the Rosenmund reduction. It selectively reduces acid chlorides to aldehydes.

Reaction: $C_{6} H_{5} C O C l \overset{H_{2} / Pd - {BaSO}_{4}}{\to} C_{6} H_{5} C H O$

So, the final product C is Benzaldehyde (C₆H₅CHO).

Final Answer

Therefore, the product C is C₆H₅CHO (Benzaldehyde).

Column-I	Column-II
	(p) Nucleophilic substitution
	(q) Electrophilic substitution
	(r) Dehydration
	(s) Nucleophilic addition
	(t) Carbanion

Detailed Solution

Step 1: Oxidation of Toluene with KMnO₄

Step 2: Conversion to Acid Chloride with SOCl₂

Step 3: Rosenmund Reduction

Final Answer

Related Topics & Formulae

Detailed Solution

Step 1: Oxidation of Toluene with KMnO₄

Step 2: Conversion to Acid Chloride with SOCl₂

Step 3: Rosenmund Reduction

Final Answer

Related Topics & Formulae

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