When menthyl chloride (see Fig. P9.78) is treated with sodium ethoxide in ethanol

Chapter 9, Problem 9.78

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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. (Hint: Draw the chair conformations of the starting materials, remember the stereochemistry of the E2 reaction, and dont forget about the chair interconversion of cyclohexanes.)

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