Question

Draw the structure of the alkyl bromide from which the alkyl acetate shown below was made by Sn2 reaction. ball & stick - + labels • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • If a group is achiral, do not use wedged or hashed bonds on it. • In cases where there is more than one answer, just draw one. • Use “flat” representations of rings, not chairs, in your drawing.

Answer 1

Please Note that, inversion of stereochemistry of a carbon may always not mean the inversion of configuration of that carbon. Here, since acetate group and bromide group, both bear the same priority on the attacked carbon, inversion of stereochemistry matches with the inversion of configuration.

Structure of the given Alkyl acetate: CH3 H3CH H3C Absolute configuration HÔ 'CH of c* = (R) ochz This was made from an alkyl bromide by SN2 reaction, which takes place by a inversion of stereochemistry of the attacked carbon atom. Therefore the Bromide will have the opposite stereochemistry of the acetate shown above. • Structure of the alkyl bromide : Br. * H 대3 CH3 Absolute configuration of c* = (S).

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