Problem: Menthyl chloride and neomenthyl chloride have the structures shown. One of these stereoisomers undergoes elimination on treatment with sodium ethoxide in ethanol much more readily than the other. Which reacts faster, menthyl chloride or neomenthyl  chloride? Why?

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Menthyl chloride and neomenthyl chloride have the structures shown. One of these stereoisomers undergoes elimination on treatment with sodium ethoxide in ethanol much more readily than the other. Which reacts faster, menthyl chloride or neomenthyl  chloride? Why?

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Based on our data, we think this problem is relevant for Professor Daoudi's class at UCF.

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Our data indicates that this problem or a close variation was asked in Organic Chemistry - Carey 8th Edition. You can also practice Organic Chemistry - Carey 8th Edition practice problems.