(a) Explain why the compound given in part (a) of Fig. P9.61 reacts to give a mixture of 2-butene stereoisomers in which only the Z isomer contains deuterium.

(b) Explain why the compound given in part (b) of Fig. P9.61 reacts to give a mixture of 2-butene stereoisomers in which only the E isomer contains deuterium.

Transcribed Image Text:

(a) (b) H3C. H₂C. H Br DH Figure P9.61 HD CH3 H Br CH3 + CHỊCH,O:- + CH3CH₂Ö:- CH3CH₂OH CH₂CH₂OH H₂C H H3C D C=C H CH3 H₂C CH3 D H H₂C H C=C C=C CH3 H CH3 H