Represent the structures of intermediates (A – C) and product D. Propose a mechanism for each of the steps.

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
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Represent the structures of intermediates (A – C) and product D. Propose a mechanism for each of the steps.

Br
CH3
NaNH2
HC-CHC
NH3, líq.
Br
NH, líq.
1. О
HO.
2. Н,О, н*
2. КОН
D 4
C
Transcribed Image Text:Br CH3 NaNH2 HC-CHC NH3, líq. Br NH, líq. 1. О HO. 2. Н,О, н* 2. КОН D 4 C
Expert Solution
Step 1-Introduction

When a group that has acidic hydrogen is treated with a base, it results in the formation of a carbanion by the removal of hydrogen. In a carbanion, the carbon atom has a unit negative charge. In an aliphatic nucleophilic substitution reaction, the nucleophile substitutes another group from the molecule and it results in the formation of a new chemical bond.     

The groups that are used to prevent a certain group from participating in the chemical reaction are termed as the protecting group. For example, the aldehyde (-CHO) functional group can be protected by treating it with glycol in the acidic medium.          

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