Single correct option
Four reactions of the butene isomers are carried out: (I) -but-2-ene with followed by ; (II) -but-2-ene with -CPBA followed by aqueous ; (III) -but-2-ene with in ; (IV) -but-2-ene with cold, dilute, alkaline . Considering only the major stereochemical course of each reaction, the reactions that give an achiral product (rather than a racemic mixture) are
- A. I and II only
- B. I and III only
- C. III and IV only
- D. II and IV only
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Answer: (A) I and II only
Treat each reaction by its stereochemistry. (I) gives syn addition of two OH groups; syn addition to the alkene gives the butane-2,3-diol. (II) The epoxide from -CPBA retains the alkene geometry, and acid-catalysed ring opening by water is anti (backside attack); net anti dihydroxylation of the alkene gives the diol. (III) Bromination is anti addition; anti addition to the alkene gives the pair, i.e. a racemic dibromide. (IV) Cold alkaline permanganate is syn addition; syn addition to the alkene gives the racemic diol. Rule: syn on or anti on gives ; syn on or anti on gives racemate. Hence only I and II give products.
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