JEE Main 2023 · 10 April · evening · Single correct · +4 / −1
Incorrect method of preparation for alcohols from the following is:
- (a) Hydroboration-oxidation of alkene.
- (b) Reaction of Ketone with RMgBr followed by hydrolysis.
- (c) Ozonolysis of alkene.
- (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.
- 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.
Option What happens Product Gives alcohol? (a) Hydroboration-oxidation BH₃ adds across C=C, then H₂O₂/OH⁻ swaps B for OH anti-Markovnikov alcohol yes (b) Ketone + RMgBr, then H₃O⁺ R adds to the carbonyl carbon, then O is protonated tertiary alcohol yes (c) Ozonolysis O₃ cleaves the C=C completely, then Zn/H₂O works up the ozonide aldehydes and/or ketones no (d) R–X + aqueous NaOH OH⁻ replaces the halogen by substitution alcohol yes - 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.
- 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.