One or more options correct
Consider the stereochemical outcome of additions to alkenes. The CORRECT statement(s) is/are
- A. Addition of in to (E)-but-2-ene gives optically inactive -2,3-dibromobutane.
- B. Addition of in to (Z)-but-2-ene gives -2,3-dibromobutane as the only product.
- C. Cold, dilute, alkaline converts (Z)-but-2-ene into optically inactive -butane-2,3-diol.
- D. Reaction of cyclohexene with in water gives -2-bromocyclohexan-1-ol as the major product.
Show answer and solution
Answer: A, C
Both addition (through a bromonium ion that is opened by backside attack) and the / route should be analysed by their stereospecificity. (A) Anti addition of 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 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.)
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