Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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Question
Chapter 12.9, Problem 18P
Interpretation Introduction
Interpretation:
The steps how the two products formed from reaction of methylenecyclohehane with NBS has to be given. Stereoisomers has to be disregarded.
Concept introduction:
Bromination of Allylic Carbons:
N-bromosuccinimide (NBS) is used for the allylic bromination through radical reaction. Bromination of allylicc carbon requires low concentration of bromine and low concentration of hydrobromic acid. If high concentration of bromine and high concentration of hydrobromic acid which leads to the formation of bromonation in the double bond.
Bromination reaction starts with the homolytic cleavage of N-Br bond in N-bromosuccinimide (NBS) which creates bromine radical to initiate the radical bromination reaction.
NBS bromine radical removes the allylic hydrogen which forms hydrogen bromide and allylic radical in the first propagation step, the allylic radical is stabilized by the double bond in ring. This allylic radical reaction with bromine molecule and forms allylic bromide in the second propagation step which are shown above.
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Chapter 12 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
Ch. 12.2 - Prob. 1PCh. 12.2 - Write the steps for formation of...Ch. 12.3 - Prob. 3PCh. 12.4 - How many alkyl chlorides are obtained from...Ch. 12.4 - Prob. 6PCh. 12.5 - Prob. 8PCh. 12.5 - a. Would chlorination or bromination produce a...Ch. 12.5 - Show how the following compounds could be prepared...Ch. 12.6 - Prob. 12PCh. 12.7 - Prob. 13P
Ch. 12.7 - Prob. 14PCh. 12.8 - Prob. 15PCh. 12.8 - Draw the stereoisomers of the major...Ch. 12.9 - Prob. 18PCh. 12.9 - How many allylic substituted bromoalkenes are...Ch. 12.9 - a. How many stereoisomers are formed from the...Ch. 12.9 - Prob. 21PCh. 12.9 - Prob. 22PCh. 12.10 - Prob. 23PCh. 12.11 - How many atoms share the unpaired electrons in...Ch. 12.11 - Prob. 25PCh. 12 - Prob. 26PCh. 12 - Prob. 27PCh. 12 - Prob. 28PCh. 12 - Prob. 29PCh. 12 - Prob. 30PCh. 12 - Prob. 31PCh. 12 - Prob. 32PCh. 12 - Prob. 33PCh. 12 - Prob. 34PCh. 12 - Prob. 35PCh. 12 - Prob. 36PCh. 12 - Prob. 37PCh. 12 - a. What five-carbon alkene forms the same product...Ch. 12 - Prob. 39PCh. 12 - Starting with cyclohexane, how could the following...Ch. 12 - a. Propose a mechanism for the following reaction:...Ch. 12 - What stereoisomers are obtained from the following...Ch. 12 - Prob. 43PCh. 12 - Prob. 44PCh. 12 - Prob. 45PCh. 12 - Draw the products of the following reactions,...Ch. 12 - Prob. 47PCh. 12 - Prob. 48PCh. 12 - Prob. 49PCh. 12 - Explain why the rate of bromination of methane...Ch. 12 - Prob. 51PCh. 12 - Prob. 1PCh. 12 - Prob. 2PCh. 12 - Prob. 3PCh. 12 - Prob. 4P
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