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Kristy Mills

Nov 11, 2024

What happens in the reaction of cyclohexanol and lithium diisopropylamide (LDA)?!?!?!?

I am currently working on a lab report that studies the dehydration of alcohols using strong acids. One of the post-lab questions involves the reaction of cyclohexanol with lithium diisopropylamide (LDA), which yields cyclohexene. However, I believe this is incorrect. The question asks why this proposed reaction is not accurate and what the correct mechanism would be. I am feeling quite confused about the role of the lithium ion in this context. Could someone please clarify this for me?

3 Answers

A
Anonymous

Feb 18, 2025

The reaction would be:

C6H11-OH + LiIpr2N(-) ===> C6H11-O(-) + Ipr2NH + Li(+)

Ipr- = (CH3)2CH-

A
Anonymous

Feb 03, 2025

To clarify the other answer, the most acidic proton in cyclohexanol is the hydroxyl proton, so it reacts with LDA in an acid-base neutralization reaction.

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