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a. Propose a mechanism for the following reaction: b. A

Chapter 11, Problem 75P

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QUESTION:

a. Propose a mechanism for the following reaction:

b. A small amount of a product containing a six-membered ring is also formed. Draw the structure of that product.

c. Why is so little six-membered ring product formed?

Questions & Answers

QUESTION:

a. Propose a mechanism for the following reaction:

b. A small amount of a product containing a six-membered ring is also formed. Draw the structure of that product.

c. Why is so little six-membered ring product formed?

ANSWER:

Solution 75P

(a)

Under the basic conditions the ring opening takes place at less hindered carbon.

The provide reaction is as follows:

The mechanism of the reaction is as follows:

Methoxide ion is a base so it attacks on the sterically less hindered carbon of the epoxide and form an alcoxide ion.

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