When menthyl chloride (see Fig. P9.78) is treated with sodium ethoxide in ethanol
Chapter 9, Problem 9.78(choose chapter or problem)
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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