JEE Main 2023 · 10 April · evening · Single correct · +4 / −1

Incorrect method of preparation for alcohols from the following is:

  1. (a) Hydroboration-oxidation of alkene.
  2. (b) Reaction of Ketone with RMgBr followed by hydrolysis.
  3. (c) Ozonolysis of alkene.
  4. (d) Reaction of alkyl halide with aqueous NaOH.
Answer and solution

Answer (c) Ozonolysis of alkene.

Solution

Chemistry ma’am · 3 steps

Ask what each reaction puts on carbon: three give an –OH, ozonolysis only gives a C=O.

  1. What we need. A method that prepares alcohols must end with an -OH group on an sp³ carbon. Check each option for the product it actually gives.
    OptionWhat happensProductGives alcohol?
    (a) Hydroboration-oxidationBH₃ adds across C=C, then H₂O₂/OH⁻ swaps B for OHanti-Markovnikov alcoholyes
    (b) Ketone + RMgBr, then H₃O⁺R adds to the carbonyl carbon, then O is protonatedtertiary alcoholyes
    (c) OzonolysisO₃ cleaves the C=C completely, then Zn/H₂O works up the ozonidealdehydes and/or ketonesno
    (d) R–X + aqueous NaOHOH⁻ replaces the halogen by substitutionalcoholyes
  2. Why ozonolysis fails. Ozone breaks the double bond into two pieces, and each former alkene carbon becomes a C=O carbon. You get carbonyl compounds, not alcohols. Reducing them to alcohols would need a separate step such as NaBH₄.
  3. So. Ozonolysis of an alkene is the incorrect method, so the answer is (c).

The idea to keep. To check a preparation, write the product it actually forms. Ozonolysis cuts a C=C into carbonyl compounds, so it gives aldehydes or ketones, never alcohols directly.

Answer from the NTA final answer key. Solution by PrepWiser.

Study Alcohols, Phenols & Ethers

Asked about 110 times in JEE Main since 2020. This question is from 2023.