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JEE Main 20154 April
Exam
JEE Main
Year
2015
Date
4 April
Subject
Chemistry
Chapter
Aldehydes and Ketones

JEE Main 2015 · 4 April · Chemistry · Aldehydes and Ketones

In the following sequence of reactions: Toluene KMnO _ 4 → A SOCl _...

In the following sequence of reactions:

Toluene\overset{{KMnO}_{4}}{\to}A\overset{{SOCl}_{2}}{\to}B\mathop{\to}_{{BaSO}_{4}}^{{H}_{2} / Pd}C<br/><br/>TheProduct<br /><br />The ProductC$ is:In the following sequence of reactions: Toluene KMnO _ 4 → A SOCl _ 2 → B → _ BaSO _ 4 ^ H _ 2 / Pd C The Product C is:In the following sequence of reactions: Toluene KMnO _ 4 → A SOCl _ 2 → B → _ BaSO _ 4 ^ H _ 2 / Pd C The Product C is:In the following sequence of reactions: Toluene KMnO _ 4 → A SOCl _ 2 → B → _ BaSO _ 4 ^ H _ 2 / Pd C The Product C is:In the following sequence of reactions: Toluene KMnO _ 4 → A SOCl _ 2 → B → _ BaSO _ 4 ^ H _ 2 / Pd C The Product C is:

Options

  1. AC6H5CHO{C}_{6}{H}_{5}CHO
  2. BC6H5COOH{C}_{6}{H}_{5}COOH
  3. CC6H5CH3{C}_{6}{H}_{5}C{H}_{3}
  4. DC6H5CH2OH{C}_{6}{H}_{5}C{H}_{2}OH

Correct answer

A. C6H5CHO{C}_{6}{H}_{5}CHO

Step-by-step solution

Treatment of an alkylbenzene with potassium permanganate results in oxidation to give benzoic acid. The position directly adjacent to an aromatic group is called the “benzylic” position. The reaction only works if there is a hydrogen attached to the carbon. Hence, toluene, on oxidation with potassium permanganate, gives benzoic acid (A)( A ).

In the following sequence of reactions: Toluene KMnO _ 4 → A SOCl _ 2 → B → _ BaSO _ 4 ^ H _ 2 / Pd C The Product C is:

Carboxylic acids reacts with thionyl chloride to form acid chlorides. Hence, benzoic acid, on reaction with thionyl chloride (SOCl2)( {SOCl}_{2} ), gives benzoyl chloride (B)( B ).

In the following sequence of reactions: Toluene KMnO _ 4 → A SOCl _ 2 → B → _ BaSO _ 4 ^ H _ 2 / Pd C The Product C is:

Next reaction is the Rosenmund reaction. It is a reaction where acid chlorides are converted into aldehydes by using hydrogen gas over palladium poisoned by barium sulfate. Hence, benzoyl chloride upon reduction with H2/Pd{H}_{2} / Pd or BaSO4{BaSO}_{4}, forms benzaldehyde (C)( C ).

In the following sequence of reactions: Toluene KMnO _ 4 → A SOCl _ 2 → B → _ BaSO _ 4 ^ H _ 2 / Pd C The Product C is:

In the following sequence of reactions: Toluene KMnO _ 4 → A SOCl _ 2 → B → _ BaSO _ 4 ^ H _ 2 / Pd C The Product C is:

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