Gce Model Questions Vol1 2019 Chemistry Question 5

Practice objective / multiple choice question 5 from the 2019 Gce Model Questions Vol1 Chemistry examination.

Gce Model Questions Vol1 2019 Chemistry Objective / Multiple Choice Medium Difficulty
Question 5 GCE_MODEL_QUESTIONS_VOL1 • 2019 • CHEMISTRY • objective

A chemist wants to prepare 4‑bromo‑2‑methylacetophenone starting from commercially available toluene. Propose a three‑step synthetic route (including reagents) that introduces the carbonyl group, the para‑bromo substituent and the ortho‑methyl group in the correct positions. Briefly justify each transformation.

Answer Options

A. 1) NBS/benzoyl peroxide → p‑bromo‑toluene; 2) KMnO₄ → p‑bromo‑benzoic acid; 3) SOCl₂ then CH₃MgBr → 4‑bromo‑2‑methylacetophenone.
B. 1) Br₂/FeCl₃ → p‑bromo‑toluene; 2) COCl₂/PCl₅ → p‑bromo‑acetyl chloride; 3) n‑BuLi then CH₃I → 4‑bromo‑2‑methylacetophenone.
C. 1) Br₂/AlCl₃ → p‑bromo‑toluene; 2) CH₃COCl/AlCl₃ (Friedel‑Crafts acylation) → p‑bromo‑acetophenone; 3) n‑BuLi then CH₃I → 4‑bromo‑2‑methylacetophenone.
Correct Answer D. 1) Br₂/FeBr₃ → p‑bromo‑toluene; 2) KMnO₄ (or CrO₃/H₂SO₄) → p‑bromoacetophenone; 3) n‑BuLi then CH₃I → 4‑bromo‑2‑methylacetophenone.
Correct Answer
D
Correct Option:
1) Br₂/FeBr₃ → p‑bromo‑toluene; 2) KMnO₄ (or CrO₃/H₂SO₄) → p‑bromoacetophenone; 3) n‑BuLi then CH₃I → 4‑bromo‑2‑methylacetophenone.

About This Question

This is Gce Model Questions Vol1 2019 Chemistry Question 5. It is one of the objective questions from the 2019 Gce Model Questions Vol1 Chemistry examination.

Difficulty level: Medium .

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