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Chapter 13, Problem 29P

(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; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 13, Problem 29P , 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; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 13, Problem 29P , 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; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 13, Problem 29P , 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; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 13, Problem 29P , 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; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 13, Problem 29P , 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; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 13, Problem 29P , 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; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 13, Problem 29P , 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; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 13, Problem 29P , 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; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 13, Problem 29P , 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; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 13, Problem 29P , 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; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 13, Problem 29P , 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; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 13, Problem 29P , 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 13 Solutions

Organic Chemistry; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card; Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition)

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