PrepRung

JEE Advanced 2017 Paper 1 · Chemistry · General Organic Chemistry and Isomerism · medium

Consider the stereochemical outcome of additions to alkenes.

One or more options correct

Consider the stereochemical outcome of additions to alkenes. The CORRECT statement(s) is/are
  1. A. Addition of Br2\mathrm{Br_2} in CCl4\mathrm{CCl_4} to (E)-but-2-ene gives optically inactive mesomeso-2,3-dibromobutane.
  2. B. Addition of Br2\mathrm{Br_2} in CCl4\mathrm{CCl_4} to (Z)-but-2-ene gives mesomeso-2,3-dibromobutane as the only product.
  3. C. Cold, dilute, alkaline KMnO4\mathrm{KMnO_4} converts (Z)-but-2-ene into optically inactive mesomeso-butane-2,3-diol.
  4. D. Reaction of cyclohexene with Br2\mathrm{Br_2} in water gives ciscis-2-bromocyclohexan-1-ol as the major product.
Show answer and solution

Answer: A, C

Both Br2\mathrm{Br_2} addition (through a bromonium ion that is opened by backside attack) and the KMnO4\mathrm{KMnO_4}/OsO4\mathrm{OsO_4} route should be analysed by their stereospecificity. (A) Anti addition of Br2\mathrm{Br_2} to the trans (E) alkene gives the (2R,3S) product, which has an internal mirror plane, hence meso: correct. (B) Anti addition to the cis (Z) alkene gives the (2R,3R) and (2S,3S) pair, a racemic mixture, not a meso compound: wrong. (C) Cold alkaline permanganate adds two OH groups on the same face (syn addition) through a cyclic manganate ester; syn addition to the cis alkene gives the (2R,3S) meso-diol: correct (the same reagent on the E alkene would give the racemic diol). (D) In bromine water the bromonium ion is opened by H2O\mathrm{H_2O} from the face opposite to bromine, so the Br and OH are trans on the ring, not cis: wrong. (2,3-Dibromobutane has exactly three stereoisomers: the (R,R)/(S,S) pair and one meso form.)
Report a mistake

Original question written in the JEE Advanced 2017 Paper 1 pattern and checked twice for the correct answer. Not an official question paper. How we write and check questions · Corrections policy · Report a mistake