When menthyl chloride (see Fig. P9.78) is treated with sodium ethoxide in ethanol, 2-menthene is the only alkene product observed. When neomenthyl chloride is subjected to the same conditions, the alkene products are mostly 3- menthene (78%) along with some 2-menthene (22%).

Explain why different alkene products are formed from the different alkyl halides, and why 3-menthene is the major product in the second reaction.

Transcribed Image Text:

H₂C- Cl menthyl chloride H₂C- CH(CH3)2 Figure P9.78 "CH(CH3)2 neomenthyl chloride EtO- EtOH EtO- EtOH H₂C- CH(CH3)2 + CI™ 2-menthene (100%) 2-menthene + H₂C- (22%) -CH(CH3)2 + Cl 3-menthene (78%)