(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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addition of hbr to a double bond with an ether (-or) substituent occurs regiospecifically to give a product in which the Br OR are bonded to the same carbon. Draw the two possible carbocation intermediates in this electrophilic addition reaction,and explain using resonance why the observed product is formed.

Please provide a complete, detailed curved-arrow mechanism for the following reaction. Include ALL lone pairs and formal charges. Using the mechanism and a few words, explain why the NaOH deprotonates at the a-position and not the b-position or the aldehyde hydrogen. Also, explain why the indicated alkene is formed in the 2nd second rather than the other possible alkene product.

Which of the following carbocations would be to rearrange? Why?

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