Question:

The correct set(s) of reactions to synthesize benzoic acid starting from benzene is/are

Updated On: Apr 11, 2025
  • (i)Br2/Fe (ii)Mg/dry ether (iii)CO2 (iv)H3O
  • (i)Br2/Fe (ii)NH3,25°C (iii)NaNO2,dil. HCl, 0° to 5°C (iv)CuCN/KCN (v)dil.HCl,△
  • (i)CH3Cl,Anhydrous AlCl3 (ii)KMnO4|⨁OH,△ (iii)H3O
  • (i)CH3COCl,Anhydrous AlCl3 (ii)Br2,NaOH (iii)H3O
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The Correct Option is A, C, D

Solution and Explanation

Goal: Convert benzene (C₆H₆) into benzoic acid (C₆H₅COOH) 

Option (A):

  1. (i) Br₂/Fe → Bromination: C₆H₆ → C₆H₅Br
  2. (ii) Mg/dry ether → Grignard reagent formation: C₆H₅Br → C₆H₅MgBr
  3. (iii) CO₂ → Carboxylation: C₆H₅MgBr + CO₂ → C₆H₅COOMgBr
  4. (iv) H₃O⁺ → Acid workup: C₆H₅COOMgBr + H₃O⁺ → C₆H₅COOH (benzoic acid)

Option (C):

  1. (i) CH₃Cl + Anhyd. AlCl₃ → Friedel–Crafts Alkylation: C₆H₆ → C₆H₅CH₃ (toluene)
  2. (ii) KMnO₄ / OH⁻ / Δ → Side-chain oxidation: C₆H₅CH₃ → C₆H₅COO⁻
  3. (iii) H₃O⁺ → Acidification: C₆H₅COO⁻ + H₃O⁺ → C₆H₅COOH

Option (D):

  1. (i) CH₃COCl + Anhyd. AlCl₃ → Friedel–Crafts Acylation: C₆H₆ → C₆H₅COCH₃ (acetophenone)
  2. (ii) Br₂, NaOH → Haloform reaction: C₆H₅COCH₃ → C₆H₅COO⁻
  3. (iii) H₃O⁺ → Acidification: C₆H₅COO⁻ + H₃O⁺ → C₆H₅COOH

Final Answer:

Correct option(s): (A), (C), and (D)

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Concepts Used:

Aldehydes, Ketones, and Carboxylic Acids

Aldehydes, Ketones, and Carboxylic Acids are carbonyl compounds that contain a carbon-oxygen double bond. These organic compounds are very important in the field of organic chemistry and also have many industrial applications.

Aldehydes:

Aldehydes are organic compounds that have the functional group -CHO.

Preparation of Aldehydes

Acid chlorides are reduced to aldehydes with hydrogen in the presence of palladium catalyst spread on barium sulfate.

Ketones:

Ketones are organic compounds that have the functional group C=O and the structure R-(C=O)-R’.

Preparation of Ketones

Acid chlorides on reaction with dialkyl cadmium produce ketones. Dialkyl cadmium themselves are prepared from Grignard reagents.

Carboxylic Acid:

Carboxylic acids are organic compounds that contain a (C=O)OH group attached to an R group (where R refers to the remaining part of the molecule).

Preparation of Carboxylic Acids

Primary alcohols are readily oxidized to carboxylic acids with common oxidizing agents such as potassium permanganate in neutral acidic or alkaline media or by potassium dichromate and chromium trioxide in acidic media.