a) Interpretation: The complete mechanism for the conversion of 3 0 alcohol given to 3 0 alkyl halide by treating with HCl involving two cationic intermediates is to be proposed. Concept introduction: Alcohols get protonated in the presence of strong acids. The protonated intermediate will lose a molecule of water to yield a carbocation. The nucleophilic attack by the halide ion will lead to the formation of the alkyl halide. To propose: The complete mechanism for the conversion of 3 0 alcohol given to 3 0 alkyl halide by treating with HCl involving two cationic intermediates.

Question

The conversion of (CH3)3CI to (CH3)2C=CH2 can occur by either a one-step or a two-step mechanism, as shown in Equations [1] and [2]. [1] + I + H₂Ö: :OH [2] q slow :OH + I¯ H₂Ö: a. What rate equation would be observed for the mechanism in Equation [1]? b. What rate equation would be observed for the mechanism in Equation [2]? c. What is the order of each rate equation (i.e., first, second, and so forth)? d. How can these rate equations be used to show which mechanism is the right one for this reaction? e. Assume Equation [1] represents an endothermic reaction and draw an energy diagram for the reaction. Label the axes, reactants, products, Ea, and AH°. Draw the structure for the transition state. f. Assume Equation [2] represents an endothermic reaction and that the product of the rate-determining step is higher in energy than the reactants or products. Draw an energy diagram for this two-step reaction. Label the axes, reactants and products for each step, and the Ea and AH° for each…

Answer 1

Question

Chapter 17.SE, Problem 30MP

Interpretation Introduction

a)

Interpretation:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates is to be proposed.

Concept introduction:

Alcohols get protonated in the presence of strong acids. The protonated intermediate will lose a molecule of water to yield a carbocation. The nucleophilic attack by the halide ion will lead to the formation of the alkyl halide.

To propose:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates.

Interpretation Introduction

b)

Interpretation:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HBr involving two cationic intermediates is to be proposed.

Concept introduction:

Alcohols get protonated in the presence of strong acids. The protonated intermediate will lose a molecule of water to yield a carbocation. The nucleophilic attack by the halide ion will lead to the formation of the alkyl halide.

To propose:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HBr involving two cationic intermediates.

Interpretation Introduction

c)

Interpretation:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates is to be proposed.

Concept introduction:

Alcohols get protonated in the presence of strong acids. The protonated intermediate will lose a molecule of water to yield a carbocation. The nucleophilic attack by the halide ion will lead to the formation of the alkyl halide.

To propose:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates.

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The conversion of (CH3)3CI to (CH3)2C=CH2 can occur by either a one-step or a two-step mechanism, as shown in Equations [1] and [2]. [1] + I + H₂Ö: :OH [2] q slow :OH + I¯ H₂Ö: a. What rate equation would be observed for the mechanism in Equation [1]? b. What rate equation would be observed for the mechanism in Equation [2]? c. What is the order of each rate equation (i.e., first, second, and so forth)? d. How can these rate equations be used to show which mechanism is the right one for this reaction? e. Assume Equation [1] represents an endothermic reaction and draw an energy diagram for the reaction. Label the axes, reactants, products, Ea, and AH°. Draw the structure for the transition state. f. Assume Equation [2] represents an endothermic reaction and that the product of the rate-determining step is higher in energy than the reactants or products. Draw an energy diagram for this two-step reaction. Label the axes, reactants and products for each step, and the Ea and AH° for each…

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Answer 2

Question

Chapter 17.SE, Problem 30MP

Interpretation Introduction

a)

Interpretation:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates is to be proposed.

Concept introduction:

Alcohols get protonated in the presence of strong acids. The protonated intermediate will lose a molecule of water to yield a carbocation. The nucleophilic attack by the halide ion will lead to the formation of the alkyl halide.

To propose:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates.

Interpretation Introduction

b)

Interpretation:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HBr involving two cationic intermediates is to be proposed.

Concept introduction:

Alcohols get protonated in the presence of strong acids. The protonated intermediate will lose a molecule of water to yield a carbocation. The nucleophilic attack by the halide ion will lead to the formation of the alkyl halide.

To propose:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HBr involving two cationic intermediates.

Interpretation Introduction

c)

Interpretation:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates is to be proposed.

Concept introduction:

Alcohols get protonated in the presence of strong acids. The protonated intermediate will lose a molecule of water to yield a carbocation. The nucleophilic attack by the halide ion will lead to the formation of the alkyl halide.

To propose:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates.

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Answer 3

Question

Chapter 17.SE, Problem 30MP

Interpretation Introduction

a)

Interpretation:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates is to be proposed.

Concept introduction:

Alcohols get protonated in the presence of strong acids. The protonated intermediate will lose a molecule of water to yield a carbocation. The nucleophilic attack by the halide ion will lead to the formation of the alkyl halide.

To propose:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates.

Interpretation Introduction

b)

Interpretation:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HBr involving two cationic intermediates is to be proposed.

Concept introduction:

Alcohols get protonated in the presence of strong acids. The protonated intermediate will lose a molecule of water to yield a carbocation. The nucleophilic attack by the halide ion will lead to the formation of the alkyl halide.

To propose:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HBr involving two cationic intermediates.

Interpretation Introduction

c)

Interpretation:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates is to be proposed.

Concept introduction:

Alcohols get protonated in the presence of strong acids. The protonated intermediate will lose a molecule of water to yield a carbocation. The nucleophilic attack by the halide ion will lead to the formation of the alkyl halide.

To propose:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates.

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Answer 4

Question

Chapter 17.SE, Problem 30MP

Interpretation Introduction

a)

Interpretation:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates is to be proposed.

Concept introduction:

Alcohols get protonated in the presence of strong acids. The protonated intermediate will lose a molecule of water to yield a carbocation. The nucleophilic attack by the halide ion will lead to the formation of the alkyl halide.

To propose:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates.

Interpretation Introduction

b)

Interpretation:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HBr involving two cationic intermediates is to be proposed.

Concept introduction:

Alcohols get protonated in the presence of strong acids. The protonated intermediate will lose a molecule of water to yield a carbocation. The nucleophilic attack by the halide ion will lead to the formation of the alkyl halide.

To propose:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HBr involving two cationic intermediates.

Interpretation Introduction

c)

Interpretation:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates is to be proposed.

Concept introduction:

Alcohols get protonated in the presence of strong acids. The protonated intermediate will lose a molecule of water to yield a carbocation. The nucleophilic attack by the halide ion will lead to the formation of the alkyl halide.

To propose:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates.

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Answer 5

Chapter 17.SE, Problem 30MP

Interpretation Introduction

a)

Interpretation:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates is to be proposed.

Concept introduction:

Alcohols get protonated in the presence of strong acids. The protonated intermediate will lose a molecule of water to yield a carbocation. The nucleophilic attack by the halide ion will lead to the formation of the alkyl halide.

To propose:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates.

Interpretation Introduction

b)

Interpretation:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HBr involving two cationic intermediates is to be proposed.

Concept introduction:

Alcohols get protonated in the presence of strong acids. The protonated intermediate will lose a molecule of water to yield a carbocation. The nucleophilic attack by the halide ion will lead to the formation of the alkyl halide.

To propose:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HBr involving two cationic intermediates.

Interpretation Introduction

c)

Interpretation:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates is to be proposed.

Concept introduction:

Alcohols get protonated in the presence of strong acids. The protonated intermediate will lose a molecule of water to yield a carbocation. The nucleophilic attack by the halide ion will lead to the formation of the alkyl halide.

To propose:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates.

Answer 6

Chapter 17.SE, Problem 30MP

Interpretation Introduction

a)

Interpretation:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates is to be proposed.

Concept introduction:

Alcohols get protonated in the presence of strong acids. The protonated intermediate will lose a molecule of water to yield a carbocation. The nucleophilic attack by the halide ion will lead to the formation of the alkyl halide.

To propose:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates.

Answer 7

Chapter 17.SE, Problem 30MP

Interpretation Introduction

a)

Interpretation:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates is to be proposed.

Concept introduction:

Alcohols get protonated in the presence of strong acids. The protonated intermediate will lose a molecule of water to yield a carbocation. The nucleophilic attack by the halide ion will lead to the formation of the alkyl halide.

To propose:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates.

Answer 8

Interpretation Introduction

b)

Interpretation:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HBr involving two cationic intermediates is to be proposed.

Concept introduction:

Alcohols get protonated in the presence of strong acids. The protonated intermediate will lose a molecule of water to yield a carbocation. The nucleophilic attack by the halide ion will lead to the formation of the alkyl halide.

To propose:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HBr involving two cationic intermediates.

Answer 9

Interpretation Introduction

b)

Interpretation:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HBr involving two cationic intermediates is to be proposed.

Concept introduction:

Alcohols get protonated in the presence of strong acids. The protonated intermediate will lose a molecule of water to yield a carbocation. The nucleophilic attack by the halide ion will lead to the formation of the alkyl halide.

To propose:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HBr involving two cationic intermediates.

Answer 10

Interpretation Introduction

c)

Interpretation:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates is to be proposed.

Concept introduction:

Alcohols get protonated in the presence of strong acids. The protonated intermediate will lose a molecule of water to yield a carbocation. The nucleophilic attack by the halide ion will lead to the formation of the alkyl halide.

To propose:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates.

Answer 11

Interpretation Introduction

c)

Interpretation:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates is to be proposed.

Concept introduction:

Alcohols get protonated in the presence of strong acids. The protonated intermediate will lose a molecule of water to yield a carbocation. The nucleophilic attack by the halide ion will lead to the formation of the alkyl halide.

To propose:

The complete mechanism for the conversion of 3⁰ alcohol given to 3⁰ alkyl halide by treating with HCl involving two cationic intermediates.

Answer 12

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Answer 23

Ch. 17.1 - Give IUPAC names for the following compounds:Ch. 17.1 - Prob. 2P Ch. 17.2 - The following data for isomeric four-carbon...Ch. 17.2 - Rank the following substances in order of...Ch. 17.2 - Prob. 5P Ch. 17.3 - Prob. 6P Ch. 17.4 - What reagent would you use to accomplish each of...Ch. 17.4 - Prob. 8P Ch. 17.5 - Prob. 9P Ch. 17.5 - Prob. 10P

Solution Summary: The author proposes the complete mechanism for the conversion of 3 0 alcohol given to 3 1 alkyl halide by treating with HCl.

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Chapter 17 Solutions