Organic Chemistry (8th Edition)

Published by Pearson
ISBN 10: 0321768418
ISBN 13: 978-0-32176-841-4

Chapter 8 - Reactions of Alkenes - Problems - Page 343: Problem 8-7 a

Answer

The mechanism used is Oxymercuration–demercuration.

Work Step by Step

The reagents used are ethanol and $NaBH_4$. The mechanism is Oxymercuration–demercuration. Steps: 1) The arrow goes from the double bond to the Hg and back from Hg to the carbon. This electrophilic attack forms a mercurinium ion. 2) Ethanol opens the ring to give an organomercurial alcohol. It attacks on the most substituted carbon. 3) Deprotonation of the ethanol happens, leaving behind a organomercurial alcohol.
Update this answer!

You can help us out by revising, improving and updating this answer.

Update this answer

After you claim an answer you’ll have 24 hours to send in a draft. An editor will review the submission and either publish your submission or provide feedback.