Br2 (excess) FHO-

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Draw the organic products formed in attached reaction.

Br2 (excess)
FHO-
Transcribed Image Text:Br2 (excess) FHO-
Expert Solution
Step 1-Introduction

The carbon atom that resides at the immediate vicinity to the functional group in a molecule is termed as the α carbon. The next carbon is denoted as the β carbon. The carbanion is a negatively charged species in which the central carbon forms three sigma bonds with the atoms. 

When the alpha carbon situated next to the electron-withdrawing group such as carbonyl, nitro, the protons attached to the carbon can be readily removed to furnish the carbanion. In other words, the alpha hydrogens are highly acidic in nature. 

Step 2-Identification of the product

Scheme (α-bromination):

Chemistry homework question answer, step 2, image 1

Explanation:

The reaction of 2,2-dimethylhexan-3-one with the base, hydroxide ion results in the formation of the carbanion. The carbanion is highly resonance stabilized due to the conjugation with the adjacent carbonyl group. On treating with the bromine molecule, a mono bromination intermediate is produced. Since there is one more alpha hydrogen in the molecule, the base removes the proton and the produced carbanion is further reacted with another molecule of bromine to yield the dibromo product (4,4-dibromo-2,2-dimethylhexan-3-one). 

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