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MCQMediumJEE Main 2023 · 12 April, Shift 1Reaction Mechanisms (Substitution, Addition, Elimination)

Chemistry Question from JEE Main 2023 · 12 April, Shift 1

The compound shown below undergoes the following reactions:

CH3-CO-CH2-CHBr-CH3→ (ii) H2O  (i) Mg ’A’ (Major Product)\text{CH}_3\text{-CO-CH}_2\text{-CHBr-CH}_3 \quad \xrightarrow[\ (ii)\ \text{H}_2\text{O}\ ]{\ (i)\ \text{Mg}\ } \quad \textbf{'A'} \ (\text{Major Product})

(that is, 44-bromopentan-2-one). 'A' is:

  • A

    CH3-CO-CH2-CH(CH3)MgBr\text{CH}_3\text{-CO-CH}_2\text{-CH}(\text{CH}_3)\text{MgBr} — the Grignard reagent itself, with the ketone untouched

  • B

    1,2-Dimethylcyclopropan-1-ol — the three-membered ring formed by intramolecular addition, bearing an −OH-\text{OH} group

  • C

    CH3-C(OH)2-CH2-CH(CH3)MgBr\text{CH}_3\text{-C}(\text{OH})_2\text{-CH}_2\text{-CH}(\text{CH}_3)\text{MgBr} — a gem-diol still carrying the −MgBr-\text{MgBr} group

  • D

    CH3-CO-CH2-CH(CH3)-C(CH3)(OH)-CH2-CHBr-CH3\text{CH}_3\text{-CO-CH}_2\text{-CH}(\text{CH}_3)\text{-C}(\text{CH}_3)(\text{OH})\text{-CH}_2\text{-CHBr-CH}_3 — the intermolecular addition product: a tertiary alcohol that retains one ketone and one C−Br\text{C}-\text{Br} bond

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