a) Interpretation: The products of the reaction shown are to be given. Concept introduction: Ethers are cleaved by strong acids. The cleavage takes place either by S N 1 or S N 2 mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S N 2 mechanism. The Br- or I- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide . Ethers with a tertiary, benzylic or an allylic group cleave either by S N 1 or E1 mechanism because these can produce a stable carbocation yielding alkenes and alcohols. To give: The products of the reaction shown.

Question

-C = C - C - + Br₂ + I" -> -C-C-c -C = C -C- + Br² + I₂ -C=C Br I + Brū + Iz -7- C - C-C- I Br Mechanism; - C = c - c - + Br - Br > - C-c-c- Br -C-C-C- + 1 - - -Ċ-Ċ'-c' - Br Br I

Answer 1

Question

Chapter 18.SE, Problem 56GP

Interpretation Introduction

a)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br- or I- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by S_N¹ or E1 mechanism because these can produce a stable carbocation yielding alkenes and alcohols.

To give:

The products of the reaction shown.

Interpretation Introduction

b)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Treatment of an alkyl halide with thiourea gives alkyl thiourea salt. The salt when hydrolyzed with aqueous bases yields the thiol. The alkyl bromide can be prepared by treating an alcohol with PBr₃.

To give:

The product of the reaction shown.

Interpretation Introduction

c)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Bromine and iodine oxidize thiols to disulfides. The reaction is reversible in nature.

To give:

The product of the reaction shown.

Interpretation Introduction

d)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Sulfides in general are easily oxidized. When treated with H₂O₂ at room temperature they are oxidized to the corresponding sulfoxides.

To give:

The product of the reaction shown.

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-C = C - C - + Br₂ + I" -> -C-C-c -C = C -C- + Br² + I₂ -C=C Br I + Brū + Iz -7- C - C-C- I Br Mechanism; - C = c - c - + Br - Br > - C-c-c- Br -C-C-C- + 1 - - -Ċ-Ċ'-c' - Br Br I

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How do I break down the reaction shown on the chalkboard and explain it correctly using the bromonium ion mechanism, instead of the (disproven) carbocation-based mechanism

Answer 2

Question

Chapter 18.SE, Problem 56GP

Interpretation Introduction

a)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br- or I- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by S_N¹ or E1 mechanism because these can produce a stable carbocation yielding alkenes and alcohols.

To give:

The products of the reaction shown.

Interpretation Introduction

b)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Treatment of an alkyl halide with thiourea gives alkyl thiourea salt. The salt when hydrolyzed with aqueous bases yields the thiol. The alkyl bromide can be prepared by treating an alcohol with PBr₃.

To give:

The product of the reaction shown.

Interpretation Introduction

c)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Bromine and iodine oxidize thiols to disulfides. The reaction is reversible in nature.

To give:

The product of the reaction shown.

Interpretation Introduction

d)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Sulfides in general are easily oxidized. When treated with H₂O₂ at room temperature they are oxidized to the corresponding sulfoxides.

To give:

The product of the reaction shown.

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Answer 3

Question

Chapter 18.SE, Problem 56GP

Interpretation Introduction

a)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br- or I- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by S_N¹ or E1 mechanism because these can produce a stable carbocation yielding alkenes and alcohols.

To give:

The products of the reaction shown.

Interpretation Introduction

b)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Treatment of an alkyl halide with thiourea gives alkyl thiourea salt. The salt when hydrolyzed with aqueous bases yields the thiol. The alkyl bromide can be prepared by treating an alcohol with PBr₃.

To give:

The product of the reaction shown.

Interpretation Introduction

c)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Bromine and iodine oxidize thiols to disulfides. The reaction is reversible in nature.

To give:

The product of the reaction shown.

Interpretation Introduction

d)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Sulfides in general are easily oxidized. When treated with H₂O₂ at room temperature they are oxidized to the corresponding sulfoxides.

To give:

The product of the reaction shown.

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Answer 4

Question

Chapter 18.SE, Problem 56GP

Interpretation Introduction

a)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br- or I- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by S_N¹ or E1 mechanism because these can produce a stable carbocation yielding alkenes and alcohols.

To give:

The products of the reaction shown.

Interpretation Introduction

b)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Treatment of an alkyl halide with thiourea gives alkyl thiourea salt. The salt when hydrolyzed with aqueous bases yields the thiol. The alkyl bromide can be prepared by treating an alcohol with PBr₃.

To give:

The product of the reaction shown.

Interpretation Introduction

c)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Bromine and iodine oxidize thiols to disulfides. The reaction is reversible in nature.

To give:

The product of the reaction shown.

Interpretation Introduction

d)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Sulfides in general are easily oxidized. When treated with H₂O₂ at room temperature they are oxidized to the corresponding sulfoxides.

To give:

The product of the reaction shown.

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Answer 5

Chapter 18.SE, Problem 56GP

Interpretation Introduction

a)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br- or I- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by S_N¹ or E1 mechanism because these can produce a stable carbocation yielding alkenes and alcohols.

To give:

The products of the reaction shown.

Interpretation Introduction

b)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Treatment of an alkyl halide with thiourea gives alkyl thiourea salt. The salt when hydrolyzed with aqueous bases yields the thiol. The alkyl bromide can be prepared by treating an alcohol with PBr₃.

To give:

The product of the reaction shown.

Interpretation Introduction

c)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Bromine and iodine oxidize thiols to disulfides. The reaction is reversible in nature.

To give:

The product of the reaction shown.

Interpretation Introduction

d)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Sulfides in general are easily oxidized. When treated with H₂O₂ at room temperature they are oxidized to the corresponding sulfoxides.

To give:

The product of the reaction shown.

Answer 6

Chapter 18.SE, Problem 56GP

Interpretation Introduction

a)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br- or I- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by S_N¹ or E1 mechanism because these can produce a stable carbocation yielding alkenes and alcohols.

To give:

The products of the reaction shown.

Answer 7

Chapter 18.SE, Problem 56GP

Interpretation Introduction

a)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br- or I- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by S_N¹ or E1 mechanism because these can produce a stable carbocation yielding alkenes and alcohols.

To give:

The products of the reaction shown.

Answer 8

Interpretation Introduction

b)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Treatment of an alkyl halide with thiourea gives alkyl thiourea salt. The salt when hydrolyzed with aqueous bases yields the thiol. The alkyl bromide can be prepared by treating an alcohol with PBr₃.

To give:

The product of the reaction shown.

Answer 9

Interpretation Introduction

b)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Treatment of an alkyl halide with thiourea gives alkyl thiourea salt. The salt when hydrolyzed with aqueous bases yields the thiol. The alkyl bromide can be prepared by treating an alcohol with PBr₃.

To give:

The product of the reaction shown.

Answer 10

Interpretation Introduction

c)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Bromine and iodine oxidize thiols to disulfides. The reaction is reversible in nature.

To give:

The product of the reaction shown.

Answer 11

Interpretation Introduction

c)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Bromine and iodine oxidize thiols to disulfides. The reaction is reversible in nature.

To give:

The product of the reaction shown.

Answer 12

Interpretation Introduction

d)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Sulfides in general are easily oxidized. When treated with H₂O₂ at room temperature they are oxidized to the corresponding sulfoxides.

To give:

The product of the reaction shown.

Answer 13

Interpretation Introduction

d)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Sulfides in general are easily oxidized. When treated with H₂O₂ at room temperature they are oxidized to the corresponding sulfoxides.

To give:

The product of the reaction shown.

Answer 14

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Answer 15

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Answer 25

Ch. 18.1 - Name the following ethers:Ch. 18.2 - Why do you suppose only symmetrical ethers are...Ch. 18.2 - How would you prepare the following ethers using a...Ch. 18.2 - Review the mechanism of oxymercuration shown in...Ch. 18.2 - How would you prepare the following ethers? Use...Ch. 18.2 - Prob. 6P Ch. 18.3 - Prob. 7P Ch. 18.3 - Write the mechanism of the acid-induced cleavage...Ch. 18.3 - Why are HI and HBr more effective than HCl in...Ch. 18.4 - What product would you expect from Claisen...

Solution Summary: The author explains that the products of the reaction shown are phenol and 1-bromo-2-methylpropane.

c)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Bromine and iodine oxidize thiols to disulfides. The reaction is reversible in nature.

To give:

The product of the reaction shown.

d)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Sulfides in general are easily oxidized. When treated with H₂O₂ at room temperature they are oxidized to the corresponding sulfoxides.

To give:

The product of the reaction shown.

Chapter 18 Solutions

Solution Summary: The author explains that the products of the reaction shown are phenol and 1-bromo-2-methylpropane.

c) Interpretation: The products of the reaction shown are to be given. Concept introduction: Bromine and iodine oxidize thiols to disulfides. The reaction is reversible in nature. To give: The product of the reaction shown.

d) Interpretation: The products of the reaction shown are to be given. Concept introduction: Sulfides in general are easily oxidized. When treated with H2O2 at room temperature they are oxidized to the corresponding sulfoxides. To give: The product of the reaction shown.

Chapter 18 Solutions

c)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Bromine and iodine oxidize thiols to disulfides. The reaction is reversible in nature.

To give:

The product of the reaction shown.

d)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Sulfides in general are easily oxidized. When treated with H₂O₂ at room temperature they are oxidized to the corresponding sulfoxides.

To give:

The product of the reaction shown.