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Predict the product of the following reaction: O Me Me H

Chapter 14, Problem 14.56

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QUESTION:

Predict the product of the following reaction: O Me Me H 1) LiAlD4 2) H2O ?

Questions & Answers

QUESTION:

Predict the product of the following reaction: O Me Me H 1) LiAlD4 2) H2O ?

ANSWER:

Step 1 of 2

This problem challenges us to predict the product of a particular reaction. We're given a substituted epoxide, and told that the reagents are lithium aluminum deuteride and also water. Lithium aluminum deuteride (LAD) reacts chemically in an identical fashion to LAH; the only difference is that the deuteride has one more neutron than the protons with which we're experienced. With that in mind,  this reaction is a simple donation of deuteride anion from the polarizable lithium aluminum deuteride complex, an anion which acts as a nucleophile and opens the epoxide.

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