a) Interpretation: To predict the product of the reaction shown with regiochemistry, if relevant. Concept introduction: Catalytic hydrogenation is a heterogeneous process which occurs with syn stereochemistry. Both hydrogens adsorbed on the catalytic surface add to the double bond from the same face. To predict: The product of the reaction shown with regiochemistry, if relevant.

Question

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Answer 1

Question

Chapter 8.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

Catalytic hydrogenation is a heterogeneous process which occurs with syn stereochemistry. Both hydrogens adsorbed on the catalytic surface add to the double bond from the same face.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is ethylbenzene.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 2

Explanation of Solution

The addition of hydrogen takes place to the double bond in the side chain with syn stereochemistry. Both hydrogens add to the double bond from the same face to yield ethylbenzene.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 3

Conclusion

The product of the reaction is ethylbenzene.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 4

Interpretation Introduction

b)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

Addition of bromine to the double bond in alkenes takes place in two steps with anti stereochemistry. In the first step a cyclic bromonium ion is formed by the attack of the Ï€ electrons of the double bond with the elimination of bromide ion. In the second step the bromide ion attacks the bromonium ion from the less shielded side to give a dibromo derivative.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 6

Explanation of Solution

In the first step the addition of bromine to the double bond in 1,2-dimethylcyclohexane results in the formation of a cyclic bromonium ion with the simultaneous elimination of a bromide ion. The large bromonium ion shields one side of the molecule. Hence the attack of the bromide ion occurs from the opposite, unshielded side to yield a trans-product.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 7

Conclusion

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 8

Interpretation Introduction

c)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

Hydroxylation of double bonds can be carried out directly by treating the alkene with osmium tetroxide, O_sO₄, in the presence of N-phenylmorpholine N-oxide. The reaction occurs with syn stereochemistry through the formation of a cyclic intermediate, called osmate, formed by the addition of O_sO₄ to the alkene in a single step. The cyclic osmate is then cleaved to give the cis-1,2-diol by treatment with NaHSO₃.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 10

Explanation of Solution

O_sO₄ adds to the double bond in the side chain from the same side to yield a cyclic osmate in a single step. When treated with NaHSO₃ the cyclic osmate gets cleaved to give the diol.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 11

Conclusion

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 12

Interpretation Introduction

d)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

The addition of chlorine to alkenes in the presence of water results in the anti addition of the halohydrin, HOCl, to the double bond. In the first step a cyclic chloronium ion is formed by the attack of the Ï€ electrons of the double bond on chlorine. In the second step water attacks the chloronium ion from the least shielded side to give an anti addition product. The addition obeys Markovnokov orientation. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 14

Explanation of Solution

The given alkene has an unsymmetrically substituted double bond in the side chain. In the first step a cyclic chloronium ion is formed by the attack of the double bond on chlorine. In the second step water attacks the the chloronium ion from the opposite less shielded side to give an intermediate which then loses a proton to yield the product.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 15

Conclusion

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 16

Interpretation Introduction

e)

Interpretation:

The product expected in the reaction shown is to be given.

Concept introduction:

The reaction given is an example of Simmons-Smith reaction. When CH₂I₂ is treated with Zn/Cu couple, iodomethylzinc iodide, ICH₂ZnI, is formed. This ICH₂ZnI transfers a CH₂ group to the double bond in alkene to form a cyclopropane ring in the product.

To give:

The product expected in the reaction shown.

Expert Solution

Answer to Problem 42AP

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 18

Explanation of Solution

When CH₂I₂ is treated with Zn/Cu couple, iodomethylzinc iodide, ICH₂ZnI, is formed. This ICH₂ZnI transfers a CH₂ group to the double bond in the side chain to form a cyclopropane ring in the product.

Conclusion

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 19

Interpretation Introduction

f)

Interpretation:

The product expected in the reaction shown is to be given.

Concept introduction:

Alkenes are oxidized to give epoxides or oxiranes when treated with peracids like meta-chloroperoxybenzoic acid. The oxygen transfer from the peroxy acids takes place with syn stereochemistry. Both the C-O bonds are formed from the same face of the double bond through a one step process without the formation of an intermediate. The oxygen atom farthest from the carbonyl group gets transferred.

To give:

The product expected in the reaction shown.

Expert Solution

Answer to Problem 42AP

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 21

Where RCO₃H = meta-chloroperoxybenzoic acid

Explanation of Solution

The oxygen transfer from the peroxy acids to the double bond in the side chain takes place with syn stereochemistry. Both the C-O bonds are formed from the same face of the double bond through a one step process without the formation of an intermediate to yield the product.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 22

Conclusion

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 23

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Answer 2

Question

Chapter 8.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

Catalytic hydrogenation is a heterogeneous process which occurs with syn stereochemistry. Both hydrogens adsorbed on the catalytic surface add to the double bond from the same face.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is ethylbenzene.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 2

Explanation of Solution

The addition of hydrogen takes place to the double bond in the side chain with syn stereochemistry. Both hydrogens add to the double bond from the same face to yield ethylbenzene.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 3

Conclusion

The product of the reaction is ethylbenzene.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 4

Interpretation Introduction

b)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

Addition of bromine to the double bond in alkenes takes place in two steps with anti stereochemistry. In the first step a cyclic bromonium ion is formed by the attack of the Ï€ electrons of the double bond with the elimination of bromide ion. In the second step the bromide ion attacks the bromonium ion from the less shielded side to give a dibromo derivative.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 6

Explanation of Solution

In the first step the addition of bromine to the double bond in 1,2-dimethylcyclohexane results in the formation of a cyclic bromonium ion with the simultaneous elimination of a bromide ion. The large bromonium ion shields one side of the molecule. Hence the attack of the bromide ion occurs from the opposite, unshielded side to yield a trans-product.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 7

Conclusion

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 8

Interpretation Introduction

c)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

Hydroxylation of double bonds can be carried out directly by treating the alkene with osmium tetroxide, O_sO₄, in the presence of N-phenylmorpholine N-oxide. The reaction occurs with syn stereochemistry through the formation of a cyclic intermediate, called osmate, formed by the addition of O_sO₄ to the alkene in a single step. The cyclic osmate is then cleaved to give the cis-1,2-diol by treatment with NaHSO₃.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 10

Explanation of Solution

O_sO₄ adds to the double bond in the side chain from the same side to yield a cyclic osmate in a single step. When treated with NaHSO₃ the cyclic osmate gets cleaved to give the diol.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 11

Conclusion

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 12

Interpretation Introduction

d)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

The addition of chlorine to alkenes in the presence of water results in the anti addition of the halohydrin, HOCl, to the double bond. In the first step a cyclic chloronium ion is formed by the attack of the Ï€ electrons of the double bond on chlorine. In the second step water attacks the chloronium ion from the least shielded side to give an anti addition product. The addition obeys Markovnokov orientation. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 14

Explanation of Solution

The given alkene has an unsymmetrically substituted double bond in the side chain. In the first step a cyclic chloronium ion is formed by the attack of the double bond on chlorine. In the second step water attacks the the chloronium ion from the opposite less shielded side to give an intermediate which then loses a proton to yield the product.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 15

Conclusion

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 16

Interpretation Introduction

e)

Interpretation:

The product expected in the reaction shown is to be given.

Concept introduction:

The reaction given is an example of Simmons-Smith reaction. When CH₂I₂ is treated with Zn/Cu couple, iodomethylzinc iodide, ICH₂ZnI, is formed. This ICH₂ZnI transfers a CH₂ group to the double bond in alkene to form a cyclopropane ring in the product.

To give:

The product expected in the reaction shown.

Expert Solution

Answer to Problem 42AP

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 18

Explanation of Solution

When CH₂I₂ is treated with Zn/Cu couple, iodomethylzinc iodide, ICH₂ZnI, is formed. This ICH₂ZnI transfers a CH₂ group to the double bond in the side chain to form a cyclopropane ring in the product.

Conclusion

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 19

Interpretation Introduction

f)

Interpretation:

The product expected in the reaction shown is to be given.

Concept introduction:

Alkenes are oxidized to give epoxides or oxiranes when treated with peracids like meta-chloroperoxybenzoic acid. The oxygen transfer from the peroxy acids takes place with syn stereochemistry. Both the C-O bonds are formed from the same face of the double bond through a one step process without the formation of an intermediate. The oxygen atom farthest from the carbonyl group gets transferred.

To give:

The product expected in the reaction shown.

Expert Solution

Answer to Problem 42AP

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 21

Where RCO₃H = meta-chloroperoxybenzoic acid

Explanation of Solution

The oxygen transfer from the peroxy acids to the double bond in the side chain takes place with syn stereochemistry. Both the C-O bonds are formed from the same face of the double bond through a one step process without the formation of an intermediate to yield the product.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 22

Conclusion

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 23

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Answer 3

Question

Chapter 8.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

Catalytic hydrogenation is a heterogeneous process which occurs with syn stereochemistry. Both hydrogens adsorbed on the catalytic surface add to the double bond from the same face.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is ethylbenzene.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 2

Explanation of Solution

The addition of hydrogen takes place to the double bond in the side chain with syn stereochemistry. Both hydrogens add to the double bond from the same face to yield ethylbenzene.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 3

Conclusion

The product of the reaction is ethylbenzene.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 4

Interpretation Introduction

b)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

Addition of bromine to the double bond in alkenes takes place in two steps with anti stereochemistry. In the first step a cyclic bromonium ion is formed by the attack of the Ï€ electrons of the double bond with the elimination of bromide ion. In the second step the bromide ion attacks the bromonium ion from the less shielded side to give a dibromo derivative.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 6

Explanation of Solution

In the first step the addition of bromine to the double bond in 1,2-dimethylcyclohexane results in the formation of a cyclic bromonium ion with the simultaneous elimination of a bromide ion. The large bromonium ion shields one side of the molecule. Hence the attack of the bromide ion occurs from the opposite, unshielded side to yield a trans-product.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 7

Conclusion

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 8

Interpretation Introduction

c)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

Hydroxylation of double bonds can be carried out directly by treating the alkene with osmium tetroxide, O_sO₄, in the presence of N-phenylmorpholine N-oxide. The reaction occurs with syn stereochemistry through the formation of a cyclic intermediate, called osmate, formed by the addition of O_sO₄ to the alkene in a single step. The cyclic osmate is then cleaved to give the cis-1,2-diol by treatment with NaHSO₃.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 10

Explanation of Solution

O_sO₄ adds to the double bond in the side chain from the same side to yield a cyclic osmate in a single step. When treated with NaHSO₃ the cyclic osmate gets cleaved to give the diol.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 11

Conclusion

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 12

Interpretation Introduction

d)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

The addition of chlorine to alkenes in the presence of water results in the anti addition of the halohydrin, HOCl, to the double bond. In the first step a cyclic chloronium ion is formed by the attack of the Ï€ electrons of the double bond on chlorine. In the second step water attacks the chloronium ion from the least shielded side to give an anti addition product. The addition obeys Markovnokov orientation. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 14

Explanation of Solution

The given alkene has an unsymmetrically substituted double bond in the side chain. In the first step a cyclic chloronium ion is formed by the attack of the double bond on chlorine. In the second step water attacks the the chloronium ion from the opposite less shielded side to give an intermediate which then loses a proton to yield the product.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 15

Conclusion

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 16

Interpretation Introduction

e)

Interpretation:

The product expected in the reaction shown is to be given.

Concept introduction:

The reaction given is an example of Simmons-Smith reaction. When CH₂I₂ is treated with Zn/Cu couple, iodomethylzinc iodide, ICH₂ZnI, is formed. This ICH₂ZnI transfers a CH₂ group to the double bond in alkene to form a cyclopropane ring in the product.

To give:

The product expected in the reaction shown.

Expert Solution

Answer to Problem 42AP

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 18

Explanation of Solution

When CH₂I₂ is treated with Zn/Cu couple, iodomethylzinc iodide, ICH₂ZnI, is formed. This ICH₂ZnI transfers a CH₂ group to the double bond in the side chain to form a cyclopropane ring in the product.

Conclusion

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 19

Interpretation Introduction

f)

Interpretation:

The product expected in the reaction shown is to be given.

Concept introduction:

Alkenes are oxidized to give epoxides or oxiranes when treated with peracids like meta-chloroperoxybenzoic acid. The oxygen transfer from the peroxy acids takes place with syn stereochemistry. Both the C-O bonds are formed from the same face of the double bond through a one step process without the formation of an intermediate. The oxygen atom farthest from the carbonyl group gets transferred.

To give:

The product expected in the reaction shown.

Expert Solution

Answer to Problem 42AP

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 21

Where RCO₃H = meta-chloroperoxybenzoic acid

Explanation of Solution

The oxygen transfer from the peroxy acids to the double bond in the side chain takes place with syn stereochemistry. Both the C-O bonds are formed from the same face of the double bond through a one step process without the formation of an intermediate to yield the product.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 22

Conclusion

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 23

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Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 4

Question

Chapter 8.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

Catalytic hydrogenation is a heterogeneous process which occurs with syn stereochemistry. Both hydrogens adsorbed on the catalytic surface add to the double bond from the same face.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is ethylbenzene.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 2

Explanation of Solution

The addition of hydrogen takes place to the double bond in the side chain with syn stereochemistry. Both hydrogens add to the double bond from the same face to yield ethylbenzene.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 3

Conclusion

The product of the reaction is ethylbenzene.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 4

Interpretation Introduction

b)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

Addition of bromine to the double bond in alkenes takes place in two steps with anti stereochemistry. In the first step a cyclic bromonium ion is formed by the attack of the Ï€ electrons of the double bond with the elimination of bromide ion. In the second step the bromide ion attacks the bromonium ion from the less shielded side to give a dibromo derivative.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 6

Explanation of Solution

In the first step the addition of bromine to the double bond in 1,2-dimethylcyclohexane results in the formation of a cyclic bromonium ion with the simultaneous elimination of a bromide ion. The large bromonium ion shields one side of the molecule. Hence the attack of the bromide ion occurs from the opposite, unshielded side to yield a trans-product.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 7

Conclusion

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 8

Interpretation Introduction

c)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

Hydroxylation of double bonds can be carried out directly by treating the alkene with osmium tetroxide, O_sO₄, in the presence of N-phenylmorpholine N-oxide. The reaction occurs with syn stereochemistry through the formation of a cyclic intermediate, called osmate, formed by the addition of O_sO₄ to the alkene in a single step. The cyclic osmate is then cleaved to give the cis-1,2-diol by treatment with NaHSO₃.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 10

Explanation of Solution

O_sO₄ adds to the double bond in the side chain from the same side to yield a cyclic osmate in a single step. When treated with NaHSO₃ the cyclic osmate gets cleaved to give the diol.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 11

Conclusion

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 12

Interpretation Introduction

d)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

The addition of chlorine to alkenes in the presence of water results in the anti addition of the halohydrin, HOCl, to the double bond. In the first step a cyclic chloronium ion is formed by the attack of the Ï€ electrons of the double bond on chlorine. In the second step water attacks the chloronium ion from the least shielded side to give an anti addition product. The addition obeys Markovnokov orientation. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 14

Explanation of Solution

The given alkene has an unsymmetrically substituted double bond in the side chain. In the first step a cyclic chloronium ion is formed by the attack of the double bond on chlorine. In the second step water attacks the the chloronium ion from the opposite less shielded side to give an intermediate which then loses a proton to yield the product.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 15

Conclusion

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 16

Interpretation Introduction

e)

Interpretation:

The product expected in the reaction shown is to be given.

Concept introduction:

The reaction given is an example of Simmons-Smith reaction. When CH₂I₂ is treated with Zn/Cu couple, iodomethylzinc iodide, ICH₂ZnI, is formed. This ICH₂ZnI transfers a CH₂ group to the double bond in alkene to form a cyclopropane ring in the product.

To give:

The product expected in the reaction shown.

Expert Solution

Answer to Problem 42AP

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 18

Explanation of Solution

When CH₂I₂ is treated with Zn/Cu couple, iodomethylzinc iodide, ICH₂ZnI, is formed. This ICH₂ZnI transfers a CH₂ group to the double bond in the side chain to form a cyclopropane ring in the product.

Conclusion

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 19

Interpretation Introduction

f)

Interpretation:

The product expected in the reaction shown is to be given.

Concept introduction:

Alkenes are oxidized to give epoxides or oxiranes when treated with peracids like meta-chloroperoxybenzoic acid. The oxygen transfer from the peroxy acids takes place with syn stereochemistry. Both the C-O bonds are formed from the same face of the double bond through a one step process without the formation of an intermediate. The oxygen atom farthest from the carbonyl group gets transferred.

To give:

The product expected in the reaction shown.

Expert Solution

Answer to Problem 42AP

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 21

Where RCO₃H = meta-chloroperoxybenzoic acid

Explanation of Solution

The oxygen transfer from the peroxy acids to the double bond in the side chain takes place with syn stereochemistry. Both the C-O bonds are formed from the same face of the double bond through a one step process without the formation of an intermediate to yield the product.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 22

Conclusion

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 23

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Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 5

Chapter 8.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

Catalytic hydrogenation is a heterogeneous process which occurs with syn stereochemistry. Both hydrogens adsorbed on the catalytic surface add to the double bond from the same face.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is ethylbenzene.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 2

Explanation of Solution

The addition of hydrogen takes place to the double bond in the side chain with syn stereochemistry. Both hydrogens add to the double bond from the same face to yield ethylbenzene.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 3

Conclusion

The product of the reaction is ethylbenzene.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 4

Interpretation Introduction

b)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

Addition of bromine to the double bond in alkenes takes place in two steps with anti stereochemistry. In the first step a cyclic bromonium ion is formed by the attack of the Ï€ electrons of the double bond with the elimination of bromide ion. In the second step the bromide ion attacks the bromonium ion from the less shielded side to give a dibromo derivative.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 6

Explanation of Solution

In the first step the addition of bromine to the double bond in 1,2-dimethylcyclohexane results in the formation of a cyclic bromonium ion with the simultaneous elimination of a bromide ion. The large bromonium ion shields one side of the molecule. Hence the attack of the bromide ion occurs from the opposite, unshielded side to yield a trans-product.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 7

Conclusion

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 8

Interpretation Introduction

c)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

Hydroxylation of double bonds can be carried out directly by treating the alkene with osmium tetroxide, O_sO₄, in the presence of N-phenylmorpholine N-oxide. The reaction occurs with syn stereochemistry through the formation of a cyclic intermediate, called osmate, formed by the addition of O_sO₄ to the alkene in a single step. The cyclic osmate is then cleaved to give the cis-1,2-diol by treatment with NaHSO₃.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 10

Explanation of Solution

O_sO₄ adds to the double bond in the side chain from the same side to yield a cyclic osmate in a single step. When treated with NaHSO₃ the cyclic osmate gets cleaved to give the diol.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 11

Conclusion

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 12

Interpretation Introduction

d)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

The addition of chlorine to alkenes in the presence of water results in the anti addition of the halohydrin, HOCl, to the double bond. In the first step a cyclic chloronium ion is formed by the attack of the Ï€ electrons of the double bond on chlorine. In the second step water attacks the chloronium ion from the least shielded side to give an anti addition product. The addition obeys Markovnokov orientation. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 14

Explanation of Solution

The given alkene has an unsymmetrically substituted double bond in the side chain. In the first step a cyclic chloronium ion is formed by the attack of the double bond on chlorine. In the second step water attacks the the chloronium ion from the opposite less shielded side to give an intermediate which then loses a proton to yield the product.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 15

Conclusion

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 16

Interpretation Introduction

e)

Interpretation:

The product expected in the reaction shown is to be given.

Concept introduction:

The reaction given is an example of Simmons-Smith reaction. When CH₂I₂ is treated with Zn/Cu couple, iodomethylzinc iodide, ICH₂ZnI, is formed. This ICH₂ZnI transfers a CH₂ group to the double bond in alkene to form a cyclopropane ring in the product.

To give:

The product expected in the reaction shown.

Expert Solution

Answer to Problem 42AP

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 18

Explanation of Solution

When CH₂I₂ is treated with Zn/Cu couple, iodomethylzinc iodide, ICH₂ZnI, is formed. This ICH₂ZnI transfers a CH₂ group to the double bond in the side chain to form a cyclopropane ring in the product.

Conclusion

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 19

Interpretation Introduction

f)

Interpretation:

The product expected in the reaction shown is to be given.

Concept introduction:

Alkenes are oxidized to give epoxides or oxiranes when treated with peracids like meta-chloroperoxybenzoic acid. The oxygen transfer from the peroxy acids takes place with syn stereochemistry. Both the C-O bonds are formed from the same face of the double bond through a one step process without the formation of an intermediate. The oxygen atom farthest from the carbonyl group gets transferred.

To give:

The product expected in the reaction shown.

Expert Solution

Answer to Problem 42AP

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 21

Where RCO₃H = meta-chloroperoxybenzoic acid

Explanation of Solution

The oxygen transfer from the peroxy acids to the double bond in the side chain takes place with syn stereochemistry. Both the C-O bonds are formed from the same face of the double bond through a one step process without the formation of an intermediate to yield the product.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 22

Conclusion

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 23

Answer 6

Chapter 8.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

Catalytic hydrogenation is a heterogeneous process which occurs with syn stereochemistry. Both hydrogens adsorbed on the catalytic surface add to the double bond from the same face.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is ethylbenzene.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 2

Explanation of Solution

The addition of hydrogen takes place to the double bond in the side chain with syn stereochemistry. Both hydrogens add to the double bond from the same face to yield ethylbenzene.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 3

Conclusion

The product of the reaction is ethylbenzene.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 4

Answer 7

Chapter 8.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

Catalytic hydrogenation is a heterogeneous process which occurs with syn stereochemistry. Both hydrogens adsorbed on the catalytic surface add to the double bond from the same face.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Answer 8

Expert Solution

Answer to Problem 42AP

The product of the reaction is ethylbenzene.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 2

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

The addition of hydrogen takes place to the double bond in the side chain with syn stereochemistry. Both hydrogens add to the double bond from the same face to yield ethylbenzene.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 3

Answer 13

Conclusion

The product of the reaction is ethylbenzene.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 4

Answer 14

Interpretation Introduction

b)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

Addition of bromine to the double bond in alkenes takes place in two steps with anti stereochemistry. In the first step a cyclic bromonium ion is formed by the attack of the Ï€ electrons of the double bond with the elimination of bromide ion. In the second step the bromide ion attacks the bromonium ion from the less shielded side to give a dibromo derivative.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 6

Explanation of Solution

In the first step the addition of bromine to the double bond in 1,2-dimethylcyclohexane results in the formation of a cyclic bromonium ion with the simultaneous elimination of a bromide ion. The large bromonium ion shields one side of the molecule. Hence the attack of the bromide ion occurs from the opposite, unshielded side to yield a trans-product.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 7

Conclusion

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 8

Answer 15

Interpretation Introduction

b)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

Addition of bromine to the double bond in alkenes takes place in two steps with anti stereochemistry. In the first step a cyclic bromonium ion is formed by the attack of the Ï€ electrons of the double bond with the elimination of bromide ion. In the second step the bromide ion attacks the bromonium ion from the less shielded side to give a dibromo derivative.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Answer 16

Expert Solution

Answer to Problem 42AP

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 6

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Explanation of Solution

In the first step the addition of bromine to the double bond in 1,2-dimethylcyclohexane results in the formation of a cyclic bromonium ion with the simultaneous elimination of a bromide ion. The large bromonium ion shields one side of the molecule. Hence the attack of the bromide ion occurs from the opposite, unshielded side to yield a trans-product.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 7

Answer 21

Conclusion

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 8

Answer 22

Interpretation Introduction

c)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

Hydroxylation of double bonds can be carried out directly by treating the alkene with osmium tetroxide, O_sO₄, in the presence of N-phenylmorpholine N-oxide. The reaction occurs with syn stereochemistry through the formation of a cyclic intermediate, called osmate, formed by the addition of O_sO₄ to the alkene in a single step. The cyclic osmate is then cleaved to give the cis-1,2-diol by treatment with NaHSO₃.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 10

Explanation of Solution

O_sO₄ adds to the double bond in the side chain from the same side to yield a cyclic osmate in a single step. When treated with NaHSO₃ the cyclic osmate gets cleaved to give the diol.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 11

Conclusion

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 12

Answer 23

Interpretation Introduction

c)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

Hydroxylation of double bonds can be carried out directly by treating the alkene with osmium tetroxide, O_sO₄, in the presence of N-phenylmorpholine N-oxide. The reaction occurs with syn stereochemistry through the formation of a cyclic intermediate, called osmate, formed by the addition of O_sO₄ to the alkene in a single step. The cyclic osmate is then cleaved to give the cis-1,2-diol by treatment with NaHSO₃.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Answer 24

Expert Solution

Answer to Problem 42AP

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 10

Answer 25

Expert Solution

Answer 26

Expert Solution

Answer 27

Expert Solution

Answer 28

Explanation of Solution

O_sO₄ adds to the double bond in the side chain from the same side to yield a cyclic osmate in a single step. When treated with NaHSO₃ the cyclic osmate gets cleaved to give the diol.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 11

Answer 29

Conclusion

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 12

Answer 30

Interpretation Introduction

d)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

The addition of chlorine to alkenes in the presence of water results in the anti addition of the halohydrin, HOCl, to the double bond. In the first step a cyclic chloronium ion is formed by the attack of the Ï€ electrons of the double bond on chlorine. In the second step water attacks the chloronium ion from the least shielded side to give an anti addition product. The addition obeys Markovnokov orientation. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Expert Solution

Answer to Problem 42AP

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 14

Explanation of Solution

The given alkene has an unsymmetrically substituted double bond in the side chain. In the first step a cyclic chloronium ion is formed by the attack of the double bond on chlorine. In the second step water attacks the the chloronium ion from the opposite less shielded side to give an intermediate which then loses a proton to yield the product.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 15

Conclusion

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 16

Answer 31

Interpretation Introduction

d)

Interpretation:

To predict the product of the reaction shown with regiochemistry, if relevant.

Concept introduction:

The addition of chlorine to alkenes in the presence of water results in the anti addition of the halohydrin, HOCl, to the double bond. In the first step a cyclic chloronium ion is formed by the attack of the Ï€ electrons of the double bond on chlorine. In the second step water attacks the chloronium ion from the least shielded side to give an anti addition product. The addition obeys Markovnokov orientation. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To predict:

The product of the reaction shown with regiochemistry, if relevant.

Answer 32

Expert Solution

Answer to Problem 42AP

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 14

Answer 33

Expert Solution

Answer 34

Expert Solution

Answer 35

Expert Solution

Answer 36

Explanation of Solution

The given alkene has an unsymmetrically substituted double bond in the side chain. In the first step a cyclic chloronium ion is formed by the attack of the double bond on chlorine. In the second step water attacks the the chloronium ion from the opposite less shielded side to give an intermediate which then loses a proton to yield the product.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 15

Answer 37

Conclusion

The product of the reaction is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 16

Answer 38

Interpretation Introduction

e)

Interpretation:

The product expected in the reaction shown is to be given.

Concept introduction:

The reaction given is an example of Simmons-Smith reaction. When CH₂I₂ is treated with Zn/Cu couple, iodomethylzinc iodide, ICH₂ZnI, is formed. This ICH₂ZnI transfers a CH₂ group to the double bond in alkene to form a cyclopropane ring in the product.

To give:

The product expected in the reaction shown.

Expert Solution

Answer to Problem 42AP

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 18

Explanation of Solution

When CH₂I₂ is treated with Zn/Cu couple, iodomethylzinc iodide, ICH₂ZnI, is formed. This ICH₂ZnI transfers a CH₂ group to the double bond in the side chain to form a cyclopropane ring in the product.

Conclusion

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 19

Answer 39

Interpretation Introduction

e)

Interpretation:

The product expected in the reaction shown is to be given.

Concept introduction:

The reaction given is an example of Simmons-Smith reaction. When CH₂I₂ is treated with Zn/Cu couple, iodomethylzinc iodide, ICH₂ZnI, is formed. This ICH₂ZnI transfers a CH₂ group to the double bond in alkene to form a cyclopropane ring in the product.

To give:

The product expected in the reaction shown.

Answer 40

Expert Solution

Answer to Problem 42AP

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 18

Answer 41

Expert Solution

Answer 42

Expert Solution

Answer 43

Expert Solution

Answer 44

Explanation of Solution

When CH₂I₂ is treated with Zn/Cu couple, iodomethylzinc iodide, ICH₂ZnI, is formed. This ICH₂ZnI transfers a CH₂ group to the double bond in the side chain to form a cyclopropane ring in the product.

Answer 45

Conclusion

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 19

Answer 46

Interpretation Introduction

f)

Interpretation:

The product expected in the reaction shown is to be given.

Concept introduction:

Alkenes are oxidized to give epoxides or oxiranes when treated with peracids like meta-chloroperoxybenzoic acid. The oxygen transfer from the peroxy acids takes place with syn stereochemistry. Both the C-O bonds are formed from the same face of the double bond through a one step process without the formation of an intermediate. The oxygen atom farthest from the carbonyl group gets transferred.

To give:

The product expected in the reaction shown.

Expert Solution

Answer to Problem 42AP

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 21

Where RCO₃H = meta-chloroperoxybenzoic acid

Explanation of Solution

The oxygen transfer from the peroxy acids to the double bond in the side chain takes place with syn stereochemistry. Both the C-O bonds are formed from the same face of the double bond through a one step process without the formation of an intermediate to yield the product.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 22

Conclusion

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 23

Answer 47

Interpretation Introduction

f)

Interpretation:

The product expected in the reaction shown is to be given.

Concept introduction:

Alkenes are oxidized to give epoxides or oxiranes when treated with peracids like meta-chloroperoxybenzoic acid. The oxygen transfer from the peroxy acids takes place with syn stereochemistry. Both the C-O bonds are formed from the same face of the double bond through a one step process without the formation of an intermediate. The oxygen atom farthest from the carbonyl group gets transferred.

To give:

The product expected in the reaction shown.

Answer 48

Expert Solution

Answer to Problem 42AP

The product expected in the reaction shown is

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 21

Where RCO₃H = meta-chloroperoxybenzoic acid

Answer 49

Expert Solution

Answer 50

Expert Solution

Answer 51

Expert Solution

Answer 52

Explanation of Solution

The oxygen transfer from the peroxy acids to the double bond in the side chain takes place with syn stereochemistry. Both the C-O bonds are formed from the same face of the double bond through a one step process without the formation of an intermediate to yield the product.

Organic Chemistry, Chapter 8.SE, Problem 42AP , additional homework tip 22