Organic Chemistry (8th Edition)

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

Chapter 8 - Reactions of Alkenes - Study Problems - Page 387: 8-48 d

Answer

The reaction is formation of carbenes by alpha elimination. It forms a cyclopropane.

Work Step by Step

The proposed mechanism is: Step 1: The $OH^-$ which comes from a strong base attacks the H in $CHBr_3$. The electrons in the bond between C-H go to the C. Step 2: The pi bonds in the double bond attack on the $CBr_2$ and the lone pair on the $CBr_2$ attack on the double bond, forming a cyclopropane across the double bond.
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