Pent-$2$-ene is treated with hot, acidic KMnO$_4$. What are the products?
AAcetic acid + propanoic acid
BPentane-$2{,}3$-diol
CPentanoic acid + water
DPent-$2$-en-$1$-ol
Answer & Solution
Correct answer: A. Acetic acid + propanoic acid
**Reagent behaviour.** *Cold, dilute* KMnO₄ (Baeyer's reagent) gives the diol — that's option D. *Hot, acidic* KMnO₄ is much more aggressive: it oxidatively cleaves the double bond
giving carboxylic acids (or CO₂ if the carbon was terminal).
**Apply to pent-2-ene.** $\mathrm{CH_3-CH=CH-CH_2-CH_3}$. Cleaving the C2=C3 bond, each side becomes its own acid:
- Left ($\mathrm{CH_3-CH}=$) → acetic acid $\mathrm{CH_3COOH}$.
- Right ($=\mathrm{CH-CH_2-CH_3}$)
→ propanoic acid $\mathrm{CH_3CH_2COOH}$.
**Why option D is tempting.** It's the *cold* dilute KMnO₄ answer (syn-diol). Read the reagent conditions carefully — temperature and acidity decide which product surfaces.
Keep practising Unit 4D: Organic Reaction Mechanisms & Techniques
Browse all Unit 4D: Organic Reaction Mechanisms & Techniques questions for JEE Advanced, or explore more Chemistry topics.
Related questions
Spot the error in the IUPAC nameSort: SN1 favoured or SN2 favoured?PMMA (Plexiglas / Lucite) is made from:A polymer that softens on heating and hardens on cooling reversibly is called:Buna-N is a copolymer of:Teflon is a polymer of:PVC (polyvinyl chloride) is obtained from:Natural rubber is a polymer of: