a) Interpretation: The products formed and the mechanism by which they are formed when tert -butyl ethyl ether is treated with HBr is to be given. Concept introduction: Ethers are cleaved by strong acids. The cleavage takes place either by SN 1 or SN 2 mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN 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 SN 1 or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols. To give: The products formed and the mechanism by which they are formed when tert -butyl ethyl ether is treated with HBr is to be given.

Question

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Answer 1

Question

Chapter 18.SE, Problem 24MP

Interpretation Introduction

a)

Interpretation:

The products formed and the mechanism by which they are formed when tert-butyl ethyl ether is treated with HBr is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when tert-butyl ethyl ether is treated with HBr is to be given.

Expert Solution

Answer to Problem 24MP

The products formed when tert-butyl ethyl ether is treated with HBr are ethanol and tert-butylbromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 2

Explanation of Solution

The reaction occurs following SN¹ mechanism. The acid protonates the ether initially and the protonated ether eliminates ethanol to produce a stable tert-butyl carbocation. In the next step the bromide ion attacks the carbocation to yield tert-butyl bromide as the product.

Conclusion

The products formed when tert-butyl ethyl ether is treated with HBr are ethanol and tert-butylbromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 3

Interpretation Introduction

b)

Interpretation:

The products formed and the mechanism by which they are formed when tert-butyl phenyl ether is treated with HBr is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when tert-butyl phenyl ether is treated with HBr.

Expert Solution

Answer to Problem 24MP

The products formed when tert-butyl phenyl ether is treated with HBr are phenol and tert-butyl bromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 5

Explanation of Solution

The reaction occurs following SN¹ mechanism. The acid protonates the ether initially and the protonated ether eliminates phenol to produce a stable tert-butyl carbocation. In the next step the bromide ion attacks the carbocation to yield tert-butyl bromide.

Conclusion

The products formed when tert-butyl phenyl ether is treated with HBr are phenol and tert-butyl bromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 6

Interpretation Introduction

c)

Interpretation:

The products formed and the mechanism by which they are formed when tert-butyl isopropyl ether is treated with HI is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when tert-butyl isopropyl ether is treated with HI.

Expert Solution

Answer to Problem 24MP

The products formed when tert-butyl isopropyl ether is treated with HI are tert-butyl bromide and 2-propanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 8

Explanation of Solution

The reaction occurs following SN¹ mechanism. The acid protonates the ether initially and the protonated ether eliminates 2-propanol to produce a stable ^tert-butyl carbocation. In the next step the iodide ion attacks the carbocation to yield ^tert-butyl iodide.

Conclusion

The products formed when tert-butyl isopropyl ether is treated with HI are tert-butyl bromide and 2-propanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 9

Interpretation Introduction

d)

Interpretation:

The products formed and the mechanism by which they are formed when ethyl 1-methylcyclohexyl ether is treated with HI is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when ethyl 1-methylcyclohexyl ether is treated with HI.

Expert Solution

Answer to Problem 24MP

The products formed when ethyl 1-methylcyclohexyl ether is treated with HI are 1-iodo-1-methylcyclohexane and ethanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 11

Explanation of Solution

The reaction occurs following SN1 mechanism. The acid protonates the ether initially and the protonated ether eliminates ethanol to produce a stable tert-butyl carbocation. In the next step the iodide ion attacks the carbocation to yield tert-butyl iodide.

Conclusion

The products formed when ethyl 1-methylcyclohexyl ether is treated with HI are 1-iodo-1-methylcyclohexane and ethanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 12

All the reactions (a), (b), (c) and (d) occur through SN1 mechanism.

All the reactions, (a), (b), (c) and (d) take place following SN¹ mechanism. The protonated epoxide first loses an alcohol to yield a stable tert-butyl carbocation which is then attacked by the halide ion.

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Answer 2

Question

Chapter 18.SE, Problem 24MP

Interpretation Introduction

a)

Interpretation:

The products formed and the mechanism by which they are formed when tert-butyl ethyl ether is treated with HBr is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when tert-butyl ethyl ether is treated with HBr is to be given.

Expert Solution

Answer to Problem 24MP

The products formed when tert-butyl ethyl ether is treated with HBr are ethanol and tert-butylbromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 2

Explanation of Solution

The reaction occurs following SN¹ mechanism. The acid protonates the ether initially and the protonated ether eliminates ethanol to produce a stable tert-butyl carbocation. In the next step the bromide ion attacks the carbocation to yield tert-butyl bromide as the product.

Conclusion

The products formed when tert-butyl ethyl ether is treated with HBr are ethanol and tert-butylbromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 3

Interpretation Introduction

b)

Interpretation:

The products formed and the mechanism by which they are formed when tert-butyl phenyl ether is treated with HBr is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when tert-butyl phenyl ether is treated with HBr.

Expert Solution

Answer to Problem 24MP

The products formed when tert-butyl phenyl ether is treated with HBr are phenol and tert-butyl bromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 5

Explanation of Solution

The reaction occurs following SN¹ mechanism. The acid protonates the ether initially and the protonated ether eliminates phenol to produce a stable tert-butyl carbocation. In the next step the bromide ion attacks the carbocation to yield tert-butyl bromide.

Conclusion

The products formed when tert-butyl phenyl ether is treated with HBr are phenol and tert-butyl bromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 6

Interpretation Introduction

c)

Interpretation:

The products formed and the mechanism by which they are formed when tert-butyl isopropyl ether is treated with HI is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when tert-butyl isopropyl ether is treated with HI.

Expert Solution

Answer to Problem 24MP

The products formed when tert-butyl isopropyl ether is treated with HI are tert-butyl bromide and 2-propanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 8

Explanation of Solution

The reaction occurs following SN¹ mechanism. The acid protonates the ether initially and the protonated ether eliminates 2-propanol to produce a stable ^tert-butyl carbocation. In the next step the iodide ion attacks the carbocation to yield ^tert-butyl iodide.

Conclusion

The products formed when tert-butyl isopropyl ether is treated with HI are tert-butyl bromide and 2-propanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 9

Interpretation Introduction

d)

Interpretation:

The products formed and the mechanism by which they are formed when ethyl 1-methylcyclohexyl ether is treated with HI is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when ethyl 1-methylcyclohexyl ether is treated with HI.

Expert Solution

Answer to Problem 24MP

The products formed when ethyl 1-methylcyclohexyl ether is treated with HI are 1-iodo-1-methylcyclohexane and ethanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 11

Explanation of Solution

The reaction occurs following SN1 mechanism. The acid protonates the ether initially and the protonated ether eliminates ethanol to produce a stable tert-butyl carbocation. In the next step the iodide ion attacks the carbocation to yield tert-butyl iodide.

Conclusion

The products formed when ethyl 1-methylcyclohexyl ether is treated with HI are 1-iodo-1-methylcyclohexane and ethanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 12

All the reactions (a), (b), (c) and (d) occur through SN1 mechanism.

All the reactions, (a), (b), (c) and (d) take place following SN¹ mechanism. The protonated epoxide first loses an alcohol to yield a stable tert-butyl carbocation which is then attacked by the halide ion.

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Answer 3

Question

Chapter 18.SE, Problem 24MP

Interpretation Introduction

a)

Interpretation:

The products formed and the mechanism by which they are formed when tert-butyl ethyl ether is treated with HBr is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when tert-butyl ethyl ether is treated with HBr is to be given.

Expert Solution

Answer to Problem 24MP

The products formed when tert-butyl ethyl ether is treated with HBr are ethanol and tert-butylbromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 2

Explanation of Solution

The reaction occurs following SN¹ mechanism. The acid protonates the ether initially and the protonated ether eliminates ethanol to produce a stable tert-butyl carbocation. In the next step the bromide ion attacks the carbocation to yield tert-butyl bromide as the product.

Conclusion

The products formed when tert-butyl ethyl ether is treated with HBr are ethanol and tert-butylbromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 3

Interpretation Introduction

b)

Interpretation:

The products formed and the mechanism by which they are formed when tert-butyl phenyl ether is treated with HBr is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when tert-butyl phenyl ether is treated with HBr.

Expert Solution

Answer to Problem 24MP

The products formed when tert-butyl phenyl ether is treated with HBr are phenol and tert-butyl bromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 5

Explanation of Solution

The reaction occurs following SN¹ mechanism. The acid protonates the ether initially and the protonated ether eliminates phenol to produce a stable tert-butyl carbocation. In the next step the bromide ion attacks the carbocation to yield tert-butyl bromide.

Conclusion

The products formed when tert-butyl phenyl ether is treated with HBr are phenol and tert-butyl bromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 6

Interpretation Introduction

c)

Interpretation:

The products formed and the mechanism by which they are formed when tert-butyl isopropyl ether is treated with HI is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when tert-butyl isopropyl ether is treated with HI.

Expert Solution

Answer to Problem 24MP

The products formed when tert-butyl isopropyl ether is treated with HI are tert-butyl bromide and 2-propanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 8

Explanation of Solution

The reaction occurs following SN¹ mechanism. The acid protonates the ether initially and the protonated ether eliminates 2-propanol to produce a stable ^tert-butyl carbocation. In the next step the iodide ion attacks the carbocation to yield ^tert-butyl iodide.

Conclusion

The products formed when tert-butyl isopropyl ether is treated with HI are tert-butyl bromide and 2-propanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 9

Interpretation Introduction

d)

Interpretation:

The products formed and the mechanism by which they are formed when ethyl 1-methylcyclohexyl ether is treated with HI is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when ethyl 1-methylcyclohexyl ether is treated with HI.

Expert Solution

Answer to Problem 24MP

The products formed when ethyl 1-methylcyclohexyl ether is treated with HI are 1-iodo-1-methylcyclohexane and ethanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 11

Explanation of Solution

The reaction occurs following SN1 mechanism. The acid protonates the ether initially and the protonated ether eliminates ethanol to produce a stable tert-butyl carbocation. In the next step the iodide ion attacks the carbocation to yield tert-butyl iodide.

Conclusion

The products formed when ethyl 1-methylcyclohexyl ether is treated with HI are 1-iodo-1-methylcyclohexane and ethanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 12

All the reactions (a), (b), (c) and (d) occur through SN1 mechanism.

All the reactions, (a), (b), (c) and (d) take place following SN¹ mechanism. The protonated epoxide first loses an alcohol to yield a stable tert-butyl carbocation which is then attacked by the halide ion.

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Answer 4

Question

Chapter 18.SE, Problem 24MP

Interpretation Introduction

a)

Interpretation:

The products formed and the mechanism by which they are formed when tert-butyl ethyl ether is treated with HBr is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when tert-butyl ethyl ether is treated with HBr is to be given.

Expert Solution

Answer to Problem 24MP

The products formed when tert-butyl ethyl ether is treated with HBr are ethanol and tert-butylbromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 2

Explanation of Solution

The reaction occurs following SN¹ mechanism. The acid protonates the ether initially and the protonated ether eliminates ethanol to produce a stable tert-butyl carbocation. In the next step the bromide ion attacks the carbocation to yield tert-butyl bromide as the product.

Conclusion

The products formed when tert-butyl ethyl ether is treated with HBr are ethanol and tert-butylbromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 3

Interpretation Introduction

b)

Interpretation:

The products formed and the mechanism by which they are formed when tert-butyl phenyl ether is treated with HBr is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when tert-butyl phenyl ether is treated with HBr.

Expert Solution

Answer to Problem 24MP

The products formed when tert-butyl phenyl ether is treated with HBr are phenol and tert-butyl bromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 5

Explanation of Solution

The reaction occurs following SN¹ mechanism. The acid protonates the ether initially and the protonated ether eliminates phenol to produce a stable tert-butyl carbocation. In the next step the bromide ion attacks the carbocation to yield tert-butyl bromide.

Conclusion

The products formed when tert-butyl phenyl ether is treated with HBr are phenol and tert-butyl bromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 6

Interpretation Introduction

c)

Interpretation:

The products formed and the mechanism by which they are formed when tert-butyl isopropyl ether is treated with HI is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when tert-butyl isopropyl ether is treated with HI.

Expert Solution

Answer to Problem 24MP

The products formed when tert-butyl isopropyl ether is treated with HI are tert-butyl bromide and 2-propanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 8

Explanation of Solution

The reaction occurs following SN¹ mechanism. The acid protonates the ether initially and the protonated ether eliminates 2-propanol to produce a stable ^tert-butyl carbocation. In the next step the iodide ion attacks the carbocation to yield ^tert-butyl iodide.

Conclusion

The products formed when tert-butyl isopropyl ether is treated with HI are tert-butyl bromide and 2-propanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 9

Interpretation Introduction

d)

Interpretation:

The products formed and the mechanism by which they are formed when ethyl 1-methylcyclohexyl ether is treated with HI is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when ethyl 1-methylcyclohexyl ether is treated with HI.

Expert Solution

Answer to Problem 24MP

The products formed when ethyl 1-methylcyclohexyl ether is treated with HI are 1-iodo-1-methylcyclohexane and ethanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 11

Explanation of Solution

The reaction occurs following SN1 mechanism. The acid protonates the ether initially and the protonated ether eliminates ethanol to produce a stable tert-butyl carbocation. In the next step the iodide ion attacks the carbocation to yield tert-butyl iodide.

Conclusion

The products formed when ethyl 1-methylcyclohexyl ether is treated with HI are 1-iodo-1-methylcyclohexane and ethanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 12

All the reactions (a), (b), (c) and (d) occur through SN1 mechanism.

All the reactions, (a), (b), (c) and (d) take place following SN¹ mechanism. The protonated epoxide first loses an alcohol to yield a stable tert-butyl carbocation which is then attacked by the halide ion.

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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 18.SE, Problem 24MP

Interpretation Introduction

a)

Interpretation:

The products formed and the mechanism by which they are formed when tert-butyl ethyl ether is treated with HBr is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when tert-butyl ethyl ether is treated with HBr is to be given.

Expert Solution

Answer to Problem 24MP

The products formed when tert-butyl ethyl ether is treated with HBr are ethanol and tert-butylbromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 2

Explanation of Solution

The reaction occurs following SN¹ mechanism. The acid protonates the ether initially and the protonated ether eliminates ethanol to produce a stable tert-butyl carbocation. In the next step the bromide ion attacks the carbocation to yield tert-butyl bromide as the product.

Conclusion

The products formed when tert-butyl ethyl ether is treated with HBr are ethanol and tert-butylbromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 3

Interpretation Introduction

b)

Interpretation:

The products formed and the mechanism by which they are formed when tert-butyl phenyl ether is treated with HBr is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when tert-butyl phenyl ether is treated with HBr.

Expert Solution

Answer to Problem 24MP

The products formed when tert-butyl phenyl ether is treated with HBr are phenol and tert-butyl bromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 5

Explanation of Solution

The reaction occurs following SN¹ mechanism. The acid protonates the ether initially and the protonated ether eliminates phenol to produce a stable tert-butyl carbocation. In the next step the bromide ion attacks the carbocation to yield tert-butyl bromide.

Conclusion

The products formed when tert-butyl phenyl ether is treated with HBr are phenol and tert-butyl bromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 6

Interpretation Introduction

c)

Interpretation:

The products formed and the mechanism by which they are formed when tert-butyl isopropyl ether is treated with HI is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when tert-butyl isopropyl ether is treated with HI.

Expert Solution

Answer to Problem 24MP

The products formed when tert-butyl isopropyl ether is treated with HI are tert-butyl bromide and 2-propanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 8

Explanation of Solution

The reaction occurs following SN¹ mechanism. The acid protonates the ether initially and the protonated ether eliminates 2-propanol to produce a stable ^tert-butyl carbocation. In the next step the iodide ion attacks the carbocation to yield ^tert-butyl iodide.

Conclusion

The products formed when tert-butyl isopropyl ether is treated with HI are tert-butyl bromide and 2-propanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 9

Interpretation Introduction

d)

Interpretation:

The products formed and the mechanism by which they are formed when ethyl 1-methylcyclohexyl ether is treated with HI is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when ethyl 1-methylcyclohexyl ether is treated with HI.

Expert Solution

Answer to Problem 24MP

The products formed when ethyl 1-methylcyclohexyl ether is treated with HI are 1-iodo-1-methylcyclohexane and ethanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 11

Explanation of Solution

The reaction occurs following SN1 mechanism. The acid protonates the ether initially and the protonated ether eliminates ethanol to produce a stable tert-butyl carbocation. In the next step the iodide ion attacks the carbocation to yield tert-butyl iodide.

Conclusion

The products formed when ethyl 1-methylcyclohexyl ether is treated with HI are 1-iodo-1-methylcyclohexane and ethanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 12

All the reactions (a), (b), (c) and (d) occur through SN1 mechanism.

All the reactions, (a), (b), (c) and (d) take place following SN¹ mechanism. The protonated epoxide first loses an alcohol to yield a stable tert-butyl carbocation which is then attacked by the halide ion.

Answer 6

Chapter 18.SE, Problem 24MP

Interpretation Introduction

a)

Interpretation:

The products formed and the mechanism by which they are formed when tert-butyl ethyl ether is treated with HBr is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when tert-butyl ethyl ether is treated with HBr is to be given.

Expert Solution

Answer to Problem 24MP

The products formed when tert-butyl ethyl ether is treated with HBr are ethanol and tert-butylbromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 2

Explanation of Solution

The reaction occurs following SN¹ mechanism. The acid protonates the ether initially and the protonated ether eliminates ethanol to produce a stable tert-butyl carbocation. In the next step the bromide ion attacks the carbocation to yield tert-butyl bromide as the product.

Conclusion

The products formed when tert-butyl ethyl ether is treated with HBr are ethanol and tert-butylbromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 3

Answer 7

Chapter 18.SE, Problem 24MP

Interpretation Introduction

a)

Interpretation:

The products formed and the mechanism by which they are formed when tert-butyl ethyl ether is treated with HBr is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when tert-butyl ethyl ether is treated with HBr is to be given.

Answer 8

Expert Solution

Answer to Problem 24MP

The products formed when tert-butyl ethyl ether is treated with HBr are ethanol and tert-butylbromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 2

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

The reaction occurs following SN¹ mechanism. The acid protonates the ether initially and the protonated ether eliminates ethanol to produce a stable tert-butyl carbocation. In the next step the bromide ion attacks the carbocation to yield tert-butyl bromide as the product.

Answer 13

Conclusion

The products formed when tert-butyl ethyl ether is treated with HBr are ethanol and tert-butylbromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 3

Answer 14

Interpretation Introduction

b)

Interpretation:

The products formed and the mechanism by which they are formed when tert-butyl phenyl ether is treated with HBr is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when tert-butyl phenyl ether is treated with HBr.

Expert Solution

Answer to Problem 24MP

The products formed when tert-butyl phenyl ether is treated with HBr are phenol and tert-butyl bromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 5

Explanation of Solution

The reaction occurs following SN¹ mechanism. The acid protonates the ether initially and the protonated ether eliminates phenol to produce a stable tert-butyl carbocation. In the next step the bromide ion attacks the carbocation to yield tert-butyl bromide.

Conclusion

The products formed when tert-butyl phenyl ether is treated with HBr are phenol and tert-butyl bromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 6

Answer 15

Interpretation Introduction

b)

Interpretation:

The products formed and the mechanism by which they are formed when tert-butyl phenyl ether is treated with HBr is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when tert-butyl phenyl ether is treated with HBr.

Answer 16

Expert Solution

Answer to Problem 24MP

The products formed when tert-butyl phenyl ether is treated with HBr are phenol and tert-butyl bromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 5

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Explanation of Solution

The reaction occurs following SN¹ mechanism. The acid protonates the ether initially and the protonated ether eliminates phenol to produce a stable tert-butyl carbocation. In the next step the bromide ion attacks the carbocation to yield tert-butyl bromide.

Answer 21

Conclusion

The products formed when tert-butyl phenyl ether is treated with HBr are phenol and tert-butyl bromide.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 6

Answer 22

Interpretation Introduction

c)

Interpretation:

The products formed and the mechanism by which they are formed when tert-butyl isopropyl ether is treated with HI is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when tert-butyl isopropyl ether is treated with HI.

Expert Solution

Answer to Problem 24MP

The products formed when tert-butyl isopropyl ether is treated with HI are tert-butyl bromide and 2-propanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 8

Explanation of Solution

The reaction occurs following SN¹ mechanism. The acid protonates the ether initially and the protonated ether eliminates 2-propanol to produce a stable ^tert-butyl carbocation. In the next step the iodide ion attacks the carbocation to yield ^tert-butyl iodide.

Conclusion

The products formed when tert-butyl isopropyl ether is treated with HI are tert-butyl bromide and 2-propanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 9

Answer 23

Interpretation Introduction

c)

Interpretation:

The products formed and the mechanism by which they are formed when tert-butyl isopropyl ether is treated with HI is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when tert-butyl isopropyl ether is treated with HI.

Answer 24

Expert Solution

Answer to Problem 24MP

The products formed when tert-butyl isopropyl ether is treated with HI are tert-butyl bromide and 2-propanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 8

Answer 25

Expert Solution

Answer 26

Expert Solution

Answer 27

Expert Solution

Answer 28

Explanation of Solution

The reaction occurs following SN¹ mechanism. The acid protonates the ether initially and the protonated ether eliminates 2-propanol to produce a stable ^tert-butyl carbocation. In the next step the iodide ion attacks the carbocation to yield ^tert-butyl iodide.

Answer 29

Conclusion

The products formed when tert-butyl isopropyl ether is treated with HI are tert-butyl bromide and 2-propanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 9

Answer 30

Interpretation Introduction

d)

Interpretation:

The products formed and the mechanism by which they are formed when ethyl 1-methylcyclohexyl ether is treated with HI is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when ethyl 1-methylcyclohexyl ether is treated with HI.

Expert Solution

Answer to Problem 24MP

The products formed when ethyl 1-methylcyclohexyl ether is treated with HI are 1-iodo-1-methylcyclohexane and ethanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 11

Explanation of Solution

The reaction occurs following SN1 mechanism. The acid protonates the ether initially and the protonated ether eliminates ethanol to produce a stable tert-butyl carbocation. In the next step the iodide ion attacks the carbocation to yield tert-butyl iodide.

Conclusion

The products formed when ethyl 1-methylcyclohexyl ether is treated with HI are 1-iodo-1-methylcyclohexane and ethanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 12

All the reactions (a), (b), (c) and (d) occur through SN1 mechanism.

All the reactions, (a), (b), (c) and (d) take place following SN¹ mechanism. The protonated epoxide first loses an alcohol to yield a stable tert-butyl carbocation which is then attacked by the halide ion.

Answer 31

Interpretation Introduction

d)

Interpretation:

The products formed and the mechanism by which they are formed when ethyl 1-methylcyclohexyl ether is treated with HI is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN¹ or SN² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN² 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 SN¹ or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.

To give:

The products formed and the mechanism by which they are formed when ethyl 1-methylcyclohexyl ether is treated with HI.

Answer 32

Expert Solution

Answer to Problem 24MP

The products formed when ethyl 1-methylcyclohexyl ether is treated with HI are 1-iodo-1-methylcyclohexane and ethanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 11

Answer 33

Expert Solution

Answer 34

Expert Solution

Answer 35

Expert Solution

Answer 36

Explanation of Solution

The reaction occurs following SN1 mechanism. The acid protonates the ether initially and the protonated ether eliminates ethanol to produce a stable tert-butyl carbocation. In the next step the iodide ion attacks the carbocation to yield tert-butyl iodide.

Answer 37

Conclusion

The products formed when ethyl 1-methylcyclohexyl ether is treated with HI are 1-iodo-1-methylcyclohexane and ethanol.

The mechanism by which they are formed is given below.

Organic Chemistry, Chapter 18.SE, Problem 24MP , additional homework tip 12

All the reactions (a), (b), (c) and (d) occur through SN1 mechanism.

All the reactions, (a), (b), (c) and (d) take place following SN¹ mechanism. The protonated epoxide first loses an alcohol to yield a stable tert-butyl carbocation which is then attacked by the halide ion.

Answer 38

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...

Answer to Problem 24MP

Explanation of Solution

Answer to Problem 24MP

Explanation of Solution

Answer to Problem 24MP

Explanation of Solution

Answer to Problem 24MP

Explanation of Solution

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