(a) Interpretation: The two carbocation intermediates that can be produced by the addition of a proton to the given allene are to be drawn. Concept introduction: Allenes are compounds with cumulated double bonds. Because of this, they are electron-rich and undergo electrophilic addition with Brønsted acids. In the first step, the proton adds generally to one carbon of the double bond forming a carbocation intermediate with the positive charge on the other carbon of the initial double bond.

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Answer 1

Question

Chapter 14, Problem 14.65P

Interpretation Introduction

(a)

Interpretation:

The two carbocation intermediates that can be produced by the addition of a proton to the given allene are to be drawn.

Concept introduction:

Allenes are compounds with cumulated double bonds. Because of this, they are electron-rich and undergo electrophilic addition with Brønsted acids. In the first step, the proton adds generally to one carbon of the double bond forming a carbocation intermediate with the positive charge on the other carbon of the initial double bond.

Interpretation Introduction

(b)

Interpretation:

The relative stabilities of the two carbocation intermediates formed by allene are to be explained.

Concept introduction:

The stability of a carbocation depends primarily on two factors, the number of alkyl groups attached to the carbon and resonance. Resonance stabilization is generally more than the stabilization because of the inductive electron-donating nature of alkyl groups. However, resonance requires the p orbitals of adjacent carbon (or other atoms) to be parallel to the empty p orbital of the carbocation.

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The reaction shown here yields three different nucleophilic substitution products that are constitutional isomers of one another. (a) Does this suggest an SN1 or Sn2 mechanism? (b) Draw the mechanism for the formation of each of these products. CH3CH2OH Br

b) Explain in detail what characteristics of the alkyl halide influence whether a mechanism will be SN1 or SN2. c) Explain in detail what characteristics of a nucleophile influence whether a reaction will be SN1 or SN2.

Refer to the reaction energy diagram to answer parts (a) through (e). (a) What is the rate-limiting STEP? (Select from 1, 2, 3, or 4) (b) The TRANSITION STATE for the fastest step is: (c) In the 3rd step which INTERMEDIATE structurally resembles the transition state according to the Hammon postulate? (d) Which STEP NUMBER is endergonic? (e) The number of intermediates in the overall reaction is:

Answer 2

Question

Chapter 14, Problem 14.65P

Interpretation Introduction

(a)

Interpretation:

The two carbocation intermediates that can be produced by the addition of a proton to the given allene are to be drawn.

Concept introduction:

Allenes are compounds with cumulated double bonds. Because of this, they are electron-rich and undergo electrophilic addition with Brønsted acids. In the first step, the proton adds generally to one carbon of the double bond forming a carbocation intermediate with the positive charge on the other carbon of the initial double bond.

Interpretation Introduction

(b)

Interpretation:

The relative stabilities of the two carbocation intermediates formed by allene are to be explained.

Concept introduction:

The stability of a carbocation depends primarily on two factors, the number of alkyl groups attached to the carbon and resonance. Resonance stabilization is generally more than the stabilization because of the inductive electron-donating nature of alkyl groups. However, resonance requires the p orbitals of adjacent carbon (or other atoms) to be parallel to the empty p orbital of the carbocation.

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Answer 3

Question

Chapter 14, Problem 14.65P

Interpretation Introduction

(a)

Interpretation:

The two carbocation intermediates that can be produced by the addition of a proton to the given allene are to be drawn.

Concept introduction:

Allenes are compounds with cumulated double bonds. Because of this, they are electron-rich and undergo electrophilic addition with Brønsted acids. In the first step, the proton adds generally to one carbon of the double bond forming a carbocation intermediate with the positive charge on the other carbon of the initial double bond.

Interpretation Introduction

(b)

Interpretation:

The relative stabilities of the two carbocation intermediates formed by allene are to be explained.

Concept introduction:

The stability of a carbocation depends primarily on two factors, the number of alkyl groups attached to the carbon and resonance. Resonance stabilization is generally more than the stabilization because of the inductive electron-donating nature of alkyl groups. However, resonance requires the p orbitals of adjacent carbon (or other atoms) to be parallel to the empty p orbital of the carbocation.

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Answer 4

Question

Chapter 14, Problem 14.65P

Interpretation Introduction

(a)

Interpretation:

The two carbocation intermediates that can be produced by the addition of a proton to the given allene are to be drawn.

Concept introduction:

Allenes are compounds with cumulated double bonds. Because of this, they are electron-rich and undergo electrophilic addition with Brønsted acids. In the first step, the proton adds generally to one carbon of the double bond forming a carbocation intermediate with the positive charge on the other carbon of the initial double bond.

Interpretation Introduction

(b)

Interpretation:

The relative stabilities of the two carbocation intermediates formed by allene are to be explained.

Concept introduction:

The stability of a carbocation depends primarily on two factors, the number of alkyl groups attached to the carbon and resonance. Resonance stabilization is generally more than the stabilization because of the inductive electron-donating nature of alkyl groups. However, resonance requires the p orbitals of adjacent carbon (or other atoms) to be parallel to the empty p orbital of the carbocation.

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Answer 5

Chapter 14, Problem 14.65P

Interpretation Introduction

(a)

Interpretation:

The two carbocation intermediates that can be produced by the addition of a proton to the given allene are to be drawn.

Concept introduction:

Allenes are compounds with cumulated double bonds. Because of this, they are electron-rich and undergo electrophilic addition with Brønsted acids. In the first step, the proton adds generally to one carbon of the double bond forming a carbocation intermediate with the positive charge on the other carbon of the initial double bond.

Interpretation Introduction

(b)

Interpretation:

The relative stabilities of the two carbocation intermediates formed by allene are to be explained.

Concept introduction:

The stability of a carbocation depends primarily on two factors, the number of alkyl groups attached to the carbon and resonance. Resonance stabilization is generally more than the stabilization because of the inductive electron-donating nature of alkyl groups. However, resonance requires the p orbitals of adjacent carbon (or other atoms) to be parallel to the empty p orbital of the carbocation.

Answer 6

Chapter 14, Problem 14.65P

Interpretation Introduction

(a)

Interpretation:

The two carbocation intermediates that can be produced by the addition of a proton to the given allene are to be drawn.

Concept introduction:

Allenes are compounds with cumulated double bonds. Because of this, they are electron-rich and undergo electrophilic addition with Brønsted acids. In the first step, the proton adds generally to one carbon of the double bond forming a carbocation intermediate with the positive charge on the other carbon of the initial double bond.

Answer 7

Chapter 14, Problem 14.65P

Interpretation Introduction

(a)

Interpretation:

The two carbocation intermediates that can be produced by the addition of a proton to the given allene are to be drawn.

Concept introduction:

Allenes are compounds with cumulated double bonds. Because of this, they are electron-rich and undergo electrophilic addition with Brønsted acids. In the first step, the proton adds generally to one carbon of the double bond forming a carbocation intermediate with the positive charge on the other carbon of the initial double bond.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The relative stabilities of the two carbocation intermediates formed by allene are to be explained.

Concept introduction:

The stability of a carbocation depends primarily on two factors, the number of alkyl groups attached to the carbon and resonance. Resonance stabilization is generally more than the stabilization because of the inductive electron-donating nature of alkyl groups. However, resonance requires the p orbitals of adjacent carbon (or other atoms) to be parallel to the empty p orbital of the carbocation.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The relative stabilities of the two carbocation intermediates formed by allene are to be explained.

Concept introduction:

The stability of a carbocation depends primarily on two factors, the number of alkyl groups attached to the carbon and resonance. Resonance stabilization is generally more than the stabilization because of the inductive electron-donating nature of alkyl groups. However, resonance requires the p orbitals of adjacent carbon (or other atoms) to be parallel to the empty p orbital of the carbocation.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 14 - Prob. 14.1P Ch. 14 - Prob. 14.2P Ch. 14 - Prob. 14.3P Ch. 14 - Prob. 14.4P Ch. 14 - Prob. 14.5P Ch. 14 - Prob. 14.6P Ch. 14 - Prob. 14.7P Ch. 14 - Prob. 14.8P Ch. 14 - Prob. 14.9P Ch. 14 - Prob. 14.10P

Solution Summary: The author explains the structure of the two carbocation intermediates produced by the addition of a proton to the given allene.

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Chapter 14 Solutions