PrepRung

JEE Advanced 2024 Paper 2 · Chemistry · General Organic Chemistry and Isomerism · medium

Four reactions of the butene isomers are carried out: (I) (Z)-but-2-ene with OsO4 followed by NaHSO3; (II) (E)-but-2-ene with m-CPBA followed by…

Single correct option

Four reactions of the butene isomers are carried out: (I) (Z)(Z)-but-2-ene with OsO4\mathrm{OsO_4} followed by NaHSO3\mathrm{NaHSO_3}; (II) (E)(E)-but-2-ene with mm-CPBA followed by aqueous H3O+\mathrm{H_3O^+}; (III) (Z)(Z)-but-2-ene with Br2\mathrm{Br_2} in CCl4\mathrm{CCl_4}; (IV) (E)(E)-but-2-ene with cold, dilute, alkaline KMnO4\mathrm{KMnO_4}. Considering only the major stereochemical course of each reaction, the reactions that give an achiral mesomeso product (rather than a racemic mixture) are
  1. A. I and II only
  2. B. I and III only
  3. C. III and IV only
  4. D. II and IV only
Show answer and solution

Answer: (A) I and II only

Treat each reaction by its stereochemistry. (I) OsO4\mathrm{OsO_4} gives syn addition of two OH groups; syn addition to the ZZ alkene gives the mesomeso butane-2,3-diol. (II) The epoxide from mm-CPBA retains the alkene geometry, and acid-catalysed ring opening by water is anti (backside attack); net anti dihydroxylation of the EE alkene gives the mesomeso diol. (III) Bromination is anti addition; anti addition to the ZZ alkene gives the (2R,3R)/(2S,3S)(2R,3R)/(2S,3S) pair, i.e. a racemic dibromide. (IV) Cold alkaline permanganate is syn addition; syn addition to the EE alkene gives the racemic (2R,3R)/(2S,3S)(2R,3R)/(2S,3S) diol. Rule: syn on ZZ or anti on EE gives mesomeso; syn on EE or anti on ZZ gives racemate. Hence only I and II give mesomeso products.
Report a mistake

Original question written in the JEE Advanced 2024 Paper 2 pattern and checked twice for the correct answer. Not an official question paper. How we write and check questions · Corrections policy · Report a mistake