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Explain why the following compound does not undergo base-catalyzed exchange in D2O even

Chapter 22, Problem 22.5

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QUESTION:

Explain why the following compound does not undergo base-catalyzed exchange in D2O even though it has an a-hydrogen.

Questions & Answers

QUESTION:

Explain why the following compound does not undergo base-catalyzed exchange in D2O even though it has an a-hydrogen.

ANSWER:

Problem 22.5

Explain why the following compound does not undergo base-catalyzed exchange in D2O even though it has an a-hydrogen.

                                                            Step by Step Solution

Step 1 of 3

A double bond cannot be imposed at the bridgehead of a bridged ring system unless the rings are large enough, according to Bredt's law.

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