Organic Chemistry, Books a la Carte Edition (8th Edition)
Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
Question
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Chapter 12, Problem 31P

(a)

Interpretation Introduction

Interpretation:

The major product of the given reaction should be given.

Concept introduction:

Radical or free radical: unpaired valence electron of an atom, molecule, or ion is called as radical.

Bond strength depends on the formation of the radical, if the radical is involving in resonance which is weakest bond strength.

Bromination of Allylic Carbons:

Organic Chemistry, Books a la Carte Edition (8th Edition), Chapter 12, Problem 31P , additional homework tip  1

N-bromosuccinimide (NBS) is used for the allylic bromination through radical reaction.  Bromination of allylic carbon requires low concentration of bromine and low concentration of hydrobromic acid. If high concentration of bromine and high concentration of hydrobromic acid are used, it leads to the formation of bromination in the double bond.

Organic Chemistry, Books a la Carte Edition (8th Edition), Chapter 12, Problem 31P , additional homework tip  2

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 reacts with bromine molecule and forms allylic bromide in the second propagation step which are shown above.

(b)

Interpretation Introduction

Interpretation:

The major product of the given reaction should be given.

Concept introduction:

Radical or free radical: unpaired valence electron of an atom, molecule, or ion is called as radical.

Bond strength is depends on the formation of the radical, if the radical is involving in resonance which is weakest bond strength.

Bromination of Allylic Carbons:

Organic Chemistry, Books a la Carte Edition (8th Edition), Chapter 12, Problem 31P , additional homework tip  3

N-bromosuccinimide (NBS) is used for the allylic bromination through radical reaction.  Bromination of allylic carbon requires low concentration of bromine and low concentration of hydrobromic acid. If high concentration of bromine and high concentration of hydrobromic acid are used, it leads to the formation of bromination in the double bond.

Organic Chemistry, Books a la Carte Edition (8th Edition), Chapter 12, Problem 31P , additional homework tip  4

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 reacts with bromine molecule and forms allylic bromide in the second propagation step which are shown above.

(c)

Interpretation Introduction

Interpretation:

The major product of the given reaction should be given.

Concept introduction:

Radical or free radical: unpaired valence electron of an atom, molecule, or ion is called as radical.

Bond strength is depends on the formation of the radical, if the radical is involving in resonance which is weakest bond strength.

Bromination of Allylic Carbons:

Organic Chemistry, Books a la Carte Edition (8th Edition), Chapter 12, Problem 31P , additional homework tip  5

N-bromosuccinimide (NBS) is used for the allylic bromination through radical reaction.  Bromination of allylic carbon requires low concentration of bromine and low concentration of hydrobromic acid. If high concentration of bromine and high concentration of hydrobromic acid are used, it leads to the formation of bromination in the double bond.

Organic Chemistry, Books a la Carte Edition (8th Edition), Chapter 12, Problem 31P , additional homework tip  6

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 reacts with bromine molecule and forms allylic bromide in the second propagation step which are shown above.

(d)

Interpretation Introduction

Interpretation:

The major product of the given reaction should be given.

Concept introduction:

Radical or free radical: unpaired valence electron of an atom, molecule, or ion is called as radical.

Bond strength is depends on the formation of the radical, if the radical is involving in resonance which is weakest bond strength.

Bromination of Allylic Carbons:

Organic Chemistry, Books a la Carte Edition (8th Edition), Chapter 12, Problem 31P , additional homework tip  7

N-bromosuccinimide (NBS) is used for the allylic bromination through radical reaction.  Bromination of allylic carbon requires low concentration of bromine and low concentration of hydrobromic acid. If high concentration of bromine and high concentration of hydrobromic acid are used, it leads to the formation of bromination in the double bond.

Organic Chemistry, Books a la Carte Edition (8th Edition), Chapter 12, Problem 31P , additional homework tip  8

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 reacts with bromine molecule and forms allylic bromide in the second propagation step which are shown above.

(e)

Interpretation Introduction

Interpretation:

The major product of the given reaction should be given.

Concept introduction:

Radical or free radical: unpaired valence electron of an atom, molecule, or ion is called as radical.

Bond strength is depends on the formation of the radical, if the radical is involving in resonance which is weakest bond strength.

Bromination of Allylic Carbons:

Organic Chemistry, Books a la Carte Edition (8th Edition), Chapter 12, Problem 31P , additional homework tip  9

N-bromosuccinimide (NBS) is used for the allylic bromination through radical reaction.  Bromination of allylic carbon requires low concentration of bromine and low concentration of hydrobromic acid. If high concentration of bromine and high concentration of hydrobromic acid are used, it leads to the formation of bromination in the double bond.

Organic Chemistry, Books a la Carte Edition (8th Edition), Chapter 12, Problem 31P , additional homework tip  10

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 reacts with bromine molecule and forms allylic bromide in the second propagation step which are shown above.

(f)

Interpretation Introduction

Interpretation:

The major product of the given reaction should be given.

Concept introduction:

Radical or free radical: unpaired valence electron of an atom, molecule, or ion is called as radical.

Bond strength is depends on the formation of the radical, if the radical is involving in resonance which is weakest bond strength.

Bromination of Allylic Carbons:

Organic Chemistry, Books a la Carte Edition (8th Edition), Chapter 12, Problem 31P , additional homework tip  11

N-bromosuccinimide (NBS) is used for the allylic bromination through radical reaction.  Bromination of allylic carbon requires low concentration of bromine and low concentration of hydrobromic acid. If high concentration of bromine and high concentration of hydrobromic acid are used, it leads to the formation of bromination in the double bond.

Organic Chemistry, Books a la Carte Edition (8th Edition), Chapter 12, Problem 31P , additional homework tip  12

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 reacts 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)

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