Please help with this question- why does this reaction only undergoes monoiodination (or why only one iodine atom is added to the ring and not 2 or 3). Also, please what happens to the ring once iodine has been substituted on it? I have attached the IR for the product
Please help with this question- why does this reaction only undergoes monoiodination (or why only one iodine atom is added to the ring and not 2 or 3). Also, please what happens to the ring once iodine has been substituted on it? I have attached the IR for the product
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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Please help with this question- why does this reaction only undergoes monoiodination (or why only one iodine atom is added to the ring and not 2 or 3).
Also, please what happens to the ring once iodine has been substituted on it?
I have attached the IR for the product
Transcribed Image Text:1000
1621.56
1243.52 1232.84
815.04
658.50
1572.37
1476.52 1464.39
1339.50
1147.64
778.68
1098.78
1421.27
1292.55
615.81
1054.41
748.47
3456.02
3202.74
1674.07
847.95
3332-25
2542.13
2161.02
Transcribed Image Text:substituent on the ring. As far as the exact location of the substitution, you'll need to predict
based on your knowledge of the types of activating/deactivating groups already substituted on
salicylamide.
NH₂
OH
1.) Nal, NaOCI, CH₂CH₂OH
2.) Na₂S₂O3. CI
NH₂
OH
As a quick reference, the mechanism for the electrophilic aromatic substitution is shown below.
The electrophile, It, is generated from 12. The nucleophile, the pi electrons of the ring, attacks I*
and loses aromaticity, forming a sigma complex. This sigma complex is a resonance stabilized
carbocation intermediate. The ring will then regain aromaticity once it is deprotonated by a
base.
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