Organic Chemistry: Principles And Mechanisms
Organic Chemistry: Principles And Mechanisms
2nd Edition
ISBN: 9780393630756
Author: KARTY, Joel
Publisher: W.w. Norton & Company,
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Chapter 25, Problem 25.26P
Interpretation Introduction

Interpretation:

How the given transformation would carry out using at least one radical chain reaction is to be explained.

Concept introduction:

The bromination at the carbon adjacent to benzylic carbon cannot be possible in single step from ethyl benzene. Thus, such transformation can be carried out through more than one reaction steps. The reaction steps for such transformation can be identified by retrosynthetic analysis. Then by reversing the reactions and adding the appropriate reagents, the synthesis can be written. Benzylic bromide can be prepared by radical reaction using NBS. Benzylic bromide, on based catalyzed dehydrogenation, undergoes elimination of HBr, forming a double bond. The bromine at carbon adjacent to benzylic position can be incorporated by anti-Markovnikov addition of HBr in the presence of peroxide.

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Identify the missing starting materials/ reagents/ products in the following reactions. Show the stereochemistry clearly in the structures, if any. If there is a major product, draw the structures of the major product with stereochemistry clearly indicated where applicable. Show only the diastereomers (you do not have to draw the pairs of enantiomers). If you believe that multiple products are formed in approximately equal amounts (hence neither is the major product), draw the structures of the products, and show the detailed mechanism of these reactions to justify the formation of the multiple products. If you believe no product is formed, explain why briefly. (6 mark for each, except f and g, which are 10 mark each)
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Chapter 25 Solutions

Organic Chemistry: Principles And Mechanisms

Ch. 25 - Prob. 25.11PCh. 25 - Prob. 25.12PCh. 25 - Prob. 25.13PCh. 25 - Prob. 25.14PCh. 25 - Prob. 25.15PCh. 25 - Prob. 25.16PCh. 25 - Prob. 25.17PCh. 25 - Prob. 25.18PCh. 25 - Prob. 25.19PCh. 25 - Prob. 25.20PCh. 25 - Prob. 25.21PCh. 25 - Prob. 25.22PCh. 25 - Prob. 25.23PCh. 25 - Prob. 25.24PCh. 25 - Prob. 25.25PCh. 25 - Prob. 25.26PCh. 25 - Prob. 25.27PCh. 25 - Prob. 25.28PCh. 25 - Prob. 25.29PCh. 25 - Prob. 25.30PCh. 25 - Prob. 25.31PCh. 25 - Prob. 25.32PCh. 25 - Prob. 25.33PCh. 25 - Prob. 25.34PCh. 25 - Prob. 25.35PCh. 25 - Prob. 25.36PCh. 25 - Prob. 25.37PCh. 25 - Prob. 25.38PCh. 25 - Prob. 25.39PCh. 25 - Prob. 25.40PCh. 25 - Prob. 25.41PCh. 25 - Prob. 25.42PCh. 25 - Prob. 25.43PCh. 25 - Prob. 25.44PCh. 25 - Prob. 25.45PCh. 25 - Prob. 25.46PCh. 25 - Prob. 25.47PCh. 25 - Prob. 25.48PCh. 25 - Prob. 25.49PCh. 25 - Prob. 25.50PCh. 25 - Prob. 25.51PCh. 25 - Prob. 25.52PCh. 25 - Prob. 25.53PCh. 25 - Prob. 25.54PCh. 25 - Prob. 25.55PCh. 25 - Prob. 25.56PCh. 25 - Prob. 25.57PCh. 25 - Prob. 25.58PCh. 25 - Prob. 25.59PCh. 25 - Prob. 25.60PCh. 25 - Prob. 25.61PCh. 25 - Prob. 25.62PCh. 25 - Prob. 25.63PCh. 25 - Prob. 25.64PCh. 25 - Prob. 25.65PCh. 25 - Prob. 25.66PCh. 25 - Prob. 25.67PCh. 25 - Prob. 25.68PCh. 25 - Prob. 25.69PCh. 25 - Prob. 25.70PCh. 25 - Prob. 25.71PCh. 25 - Prob. 25.72PCh. 25 - Prob. 25.73PCh. 25 - Prob. 25.74PCh. 25 - Prob. 25.75PCh. 25 - Prob. 25.76PCh. 25 - Prob. 25.77PCh. 25 - Prob. 25.1YTCh. 25 - Prob. 25.2YTCh. 25 - Prob. 25.3YTCh. 25 - Prob. 25.4YTCh. 25 - Prob. 25.5YTCh. 25 - Prob. 25.6YTCh. 25 - Prob. 25.7YTCh. 25 - Prob. 25.8YTCh. 25 - Prob. 25.9YTCh. 25 - Prob. 25.10YTCh. 25 - Prob. 25.11YTCh. 25 - Prob. 25.12YTCh. 25 - Prob. 25.13YTCh. 25 - Prob. 25.14YTCh. 25 - Prob. 25.15YTCh. 25 - Prob. 25.16YTCh. 25 - Prob. 25.17YTCh. 25 - Prob. 25.18YTCh. 25 - Prob. 25.19YTCh. 25 - Prob. 25.20YTCh. 25 - Prob. 25.21YTCh. 25 - Prob. 25.22YTCh. 25 - Prob. 25.23YTCh. 25 - Prob. 25.24YT
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