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COMEDK · Chemistry · 14. Hydrocarbons

An unsaturated hydrocarbon \([\mathrm{A}]\) reacts with \(\mathrm{HBr}\) in presence of Benzoyl peroxide to yield [B]
Compound [A] when reacted with cold, dilute alkaline \(\mathrm{KMnO}_4\) gave compound [C], 2-Methylbutane-2, 3-diol But when [A] is reacted with hot \(\mathrm{KMnO}_4\), it yielded \(\mathrm{CH}_3 \mathrm{COOH}\) and a compound [D] Identify compounds [A], [B] and [D]

  1. A [A] 2-Methylbut-2-ene
    [B] 2-Bromo-3-methylbutane
    [D] Propanone
  2. B [A] Pent-2-ene
    [B] 2-Bromopentane
    [D] Propanal
  3. C [A] Pent-1-ene
    [B] 1-Bromopentane
    [D] Propanoic acid
  4. D [A] 3-Methylbut-1-ene
    [B] 1-Bromo-3-methylbutane
    [D] Propanoic acid.
Verified Solution

Answer & Solution

Correct Answer

(A) [A] 2-Methylbut-2-ene
[B] 2-Bromo-3-methylbutane
[D] Propanone

Step-by-step Solution

Detailed explanation

Compound [A] reacts with cold, dilute alkaline \(\text{KMnO}_{4}\) to form 2-methylbutane-2,3-diol. This reaction is a syn-hydroxylation of an alkene. The structure of 2-methylbutane-2,3-diol is \(\text{CH}_{3}-\text{C(OH)(CH}_{3})-\text{CH(OH)}-\text{CH}_{3}\). The…