(a) Interpretation: The complete, detailed mechanism for the reaction is to be drawn that follows an E1 reaction pathway. Concept introduction: E1 reaction is a unimolecular elimination reaction which takes place in two steps. In the first step, the bond between the carbon atom and the leaving group breaks to generate a carbocation, which is known as a heterolysis step. In the second step, a base removes a proton, forming an alkene . A proton transfer reaction is handy and can be incorporated in the mechanism of an E1 elimination to avoid the formation of incompatible species. In case of strong acidic reaction conditions, the first preferred step is a proton transfer reaction to protonate the OH group in alcohols. Energy in the form of heat is provided for an endothermic reaction. A proton transfer reaction is handy and can be used in the reaction mechanism so as to avoid generation of non-compatible species that would interfere with the reaction medium.

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Answer 1

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Chapter 8, Problem 8.61P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the reaction is to be drawn that follows an E1 reaction pathway.

Concept introduction:

E1 reaction is a unimolecular elimination reaction which takes place in two steps. In the first step, the bond between the carbon atom and the leaving group breaks to generate a carbocation, which is known as a heterolysis step. In the second step, a base removes a proton, forming an alkene. A proton transfer reaction is handy and can be incorporated in the mechanism of an E1 elimination to avoid the formation of incompatible species. In case of strong acidic reaction conditions, the first preferred step is a proton transfer reaction to protonate the OH group in alcohols. Energy in the form of heat is provided for an endothermic reaction. A proton transfer reaction is handy and can be used in the reaction mechanism so as to avoid generation of non-compatible species that would interfere with the reaction medium.

Interpretation Introduction

(b)

Interpretation:

Free energy diagram that agrees with the mechanism in part a) is to be drawn labeling overall reactants, overall products, all transition states, and all intermediates.

Concept introduction:

E1 reaction is a unimolecular elimination reaction, which takes place in two steps. In the first step, the bond between the carbon atom and the leaving group breaks to generate a carbocation, which is known as a heterolysis step. In the second step, a base removes a proton, forming an alkene. The free energy diagram is a plot of free energy vs reaction coordinates. As E1 reaction occurs in two steps, there are two transition states with one intermediate which supports the mechanism. The overall reactants are shown on the far left; the overall products are shown on the far right, and the intermediates appear at the local energy minimum in between.

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1,4-Dimethyl-1,3-cyclohexadiene can undergo 1,2- or 1,4-addition with hydrogen halides. (a) 1,2-Addition i. Draw the carbocation intermediate(s) formed during the 1,2-addition of hydrobromic acid to 1,4-dimethyl-1,3-cyclohexadiene. ii. What is the major 1,2-addition product formed during the reaction in (i)? (b) 1,4-Addition i. Draw the carbocation intermediate(s) formed during the 1,4-addition of hydrobromic acid to 1,4-dimethyl-1,3-cyclohexadiene. ii. What is the major 1,4-addition product formed from the reaction in (i)? (c) What is the kinetic product from the reaction of one mole of hydrobromic acid with 1,4-dimethyl-1,3-cyclohexadiene? Explain your reasoning. (d) What is the thermodynamic product from the reaction of one mole of hydrobro-mic acid with 1,4-dimethyl-1,3-cyclohexadiene? Explain your reasoning. (e) What major product will result when 1,4-dimethyl-1,3-cyclohexadiene is treated with one mole of hydrobromic acid at - 78 deg * C ? Explain your reasoning.

Answer 2

Question

Chapter 8, Problem 8.61P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the reaction is to be drawn that follows an E1 reaction pathway.

Concept introduction:

E1 reaction is a unimolecular elimination reaction which takes place in two steps. In the first step, the bond between the carbon atom and the leaving group breaks to generate a carbocation, which is known as a heterolysis step. In the second step, a base removes a proton, forming an alkene. A proton transfer reaction is handy and can be incorporated in the mechanism of an E1 elimination to avoid the formation of incompatible species. In case of strong acidic reaction conditions, the first preferred step is a proton transfer reaction to protonate the OH group in alcohols. Energy in the form of heat is provided for an endothermic reaction. A proton transfer reaction is handy and can be used in the reaction mechanism so as to avoid generation of non-compatible species that would interfere with the reaction medium.

Interpretation Introduction

(b)

Interpretation:

Free energy diagram that agrees with the mechanism in part a) is to be drawn labeling overall reactants, overall products, all transition states, and all intermediates.

Concept introduction:

E1 reaction is a unimolecular elimination reaction, which takes place in two steps. In the first step, the bond between the carbon atom and the leaving group breaks to generate a carbocation, which is known as a heterolysis step. In the second step, a base removes a proton, forming an alkene. The free energy diagram is a plot of free energy vs reaction coordinates. As E1 reaction occurs in two steps, there are two transition states with one intermediate which supports the mechanism. The overall reactants are shown on the far left; the overall products are shown on the far right, and the intermediates appear at the local energy minimum in between.

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Answer 3

Question

Chapter 8, Problem 8.61P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the reaction is to be drawn that follows an E1 reaction pathway.

Concept introduction:

E1 reaction is a unimolecular elimination reaction which takes place in two steps. In the first step, the bond between the carbon atom and the leaving group breaks to generate a carbocation, which is known as a heterolysis step. In the second step, a base removes a proton, forming an alkene. A proton transfer reaction is handy and can be incorporated in the mechanism of an E1 elimination to avoid the formation of incompatible species. In case of strong acidic reaction conditions, the first preferred step is a proton transfer reaction to protonate the OH group in alcohols. Energy in the form of heat is provided for an endothermic reaction. A proton transfer reaction is handy and can be used in the reaction mechanism so as to avoid generation of non-compatible species that would interfere with the reaction medium.

Interpretation Introduction

(b)

Interpretation:

Free energy diagram that agrees with the mechanism in part a) is to be drawn labeling overall reactants, overall products, all transition states, and all intermediates.

Concept introduction:

E1 reaction is a unimolecular elimination reaction, which takes place in two steps. In the first step, the bond between the carbon atom and the leaving group breaks to generate a carbocation, which is known as a heterolysis step. In the second step, a base removes a proton, forming an alkene. The free energy diagram is a plot of free energy vs reaction coordinates. As E1 reaction occurs in two steps, there are two transition states with one intermediate which supports the mechanism. The overall reactants are shown on the far left; the overall products are shown on the far right, and the intermediates appear at the local energy minimum in between.

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Answer 4

Question

Chapter 8, Problem 8.61P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the reaction is to be drawn that follows an E1 reaction pathway.

Concept introduction:

E1 reaction is a unimolecular elimination reaction which takes place in two steps. In the first step, the bond between the carbon atom and the leaving group breaks to generate a carbocation, which is known as a heterolysis step. In the second step, a base removes a proton, forming an alkene. A proton transfer reaction is handy and can be incorporated in the mechanism of an E1 elimination to avoid the formation of incompatible species. In case of strong acidic reaction conditions, the first preferred step is a proton transfer reaction to protonate the OH group in alcohols. Energy in the form of heat is provided for an endothermic reaction. A proton transfer reaction is handy and can be used in the reaction mechanism so as to avoid generation of non-compatible species that would interfere with the reaction medium.

Interpretation Introduction

(b)

Interpretation:

Free energy diagram that agrees with the mechanism in part a) is to be drawn labeling overall reactants, overall products, all transition states, and all intermediates.

Concept introduction:

E1 reaction is a unimolecular elimination reaction, which takes place in two steps. In the first step, the bond between the carbon atom and the leaving group breaks to generate a carbocation, which is known as a heterolysis step. In the second step, a base removes a proton, forming an alkene. The free energy diagram is a plot of free energy vs reaction coordinates. As E1 reaction occurs in two steps, there are two transition states with one intermediate which supports the mechanism. The overall reactants are shown on the far left; the overall products are shown on the far right, and the intermediates appear at the local energy minimum in between.

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Answer 5

Chapter 8, Problem 8.61P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the reaction is to be drawn that follows an E1 reaction pathway.

Concept introduction:

E1 reaction is a unimolecular elimination reaction which takes place in two steps. In the first step, the bond between the carbon atom and the leaving group breaks to generate a carbocation, which is known as a heterolysis step. In the second step, a base removes a proton, forming an alkene. A proton transfer reaction is handy and can be incorporated in the mechanism of an E1 elimination to avoid the formation of incompatible species. In case of strong acidic reaction conditions, the first preferred step is a proton transfer reaction to protonate the OH group in alcohols. Energy in the form of heat is provided for an endothermic reaction. A proton transfer reaction is handy and can be used in the reaction mechanism so as to avoid generation of non-compatible species that would interfere with the reaction medium.

Interpretation Introduction

(b)

Interpretation:

Free energy diagram that agrees with the mechanism in part a) is to be drawn labeling overall reactants, overall products, all transition states, and all intermediates.

Concept introduction:

E1 reaction is a unimolecular elimination reaction, which takes place in two steps. In the first step, the bond between the carbon atom and the leaving group breaks to generate a carbocation, which is known as a heterolysis step. In the second step, a base removes a proton, forming an alkene. The free energy diagram is a plot of free energy vs reaction coordinates. As E1 reaction occurs in two steps, there are two transition states with one intermediate which supports the mechanism. The overall reactants are shown on the far left; the overall products are shown on the far right, and the intermediates appear at the local energy minimum in between.

Answer 6

Chapter 8, Problem 8.61P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the reaction is to be drawn that follows an E1 reaction pathway.

Concept introduction:

E1 reaction is a unimolecular elimination reaction which takes place in two steps. In the first step, the bond between the carbon atom and the leaving group breaks to generate a carbocation, which is known as a heterolysis step. In the second step, a base removes a proton, forming an alkene. A proton transfer reaction is handy and can be incorporated in the mechanism of an E1 elimination to avoid the formation of incompatible species. In case of strong acidic reaction conditions, the first preferred step is a proton transfer reaction to protonate the OH group in alcohols. Energy in the form of heat is provided for an endothermic reaction. A proton transfer reaction is handy and can be used in the reaction mechanism so as to avoid generation of non-compatible species that would interfere with the reaction medium.

Answer 7

Chapter 8, Problem 8.61P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the reaction is to be drawn that follows an E1 reaction pathway.

Concept introduction:

E1 reaction is a unimolecular elimination reaction which takes place in two steps. In the first step, the bond between the carbon atom and the leaving group breaks to generate a carbocation, which is known as a heterolysis step. In the second step, a base removes a proton, forming an alkene. A proton transfer reaction is handy and can be incorporated in the mechanism of an E1 elimination to avoid the formation of incompatible species. In case of strong acidic reaction conditions, the first preferred step is a proton transfer reaction to protonate the OH group in alcohols. Energy in the form of heat is provided for an endothermic reaction. A proton transfer reaction is handy and can be used in the reaction mechanism so as to avoid generation of non-compatible species that would interfere with the reaction medium.

Answer 8

Interpretation Introduction

(b)

Interpretation:

Free energy diagram that agrees with the mechanism in part a) is to be drawn labeling overall reactants, overall products, all transition states, and all intermediates.

Concept introduction:

E1 reaction is a unimolecular elimination reaction, which takes place in two steps. In the first step, the bond between the carbon atom and the leaving group breaks to generate a carbocation, which is known as a heterolysis step. In the second step, a base removes a proton, forming an alkene. The free energy diagram is a plot of free energy vs reaction coordinates. As E1 reaction occurs in two steps, there are two transition states with one intermediate which supports the mechanism. The overall reactants are shown on the far left; the overall products are shown on the far right, and the intermediates appear at the local energy minimum in between.

Answer 9

Interpretation Introduction

(b)

Interpretation:

Free energy diagram that agrees with the mechanism in part a) is to be drawn labeling overall reactants, overall products, all transition states, and all intermediates.

Concept introduction:

E1 reaction is a unimolecular elimination reaction, which takes place in two steps. In the first step, the bond between the carbon atom and the leaving group breaks to generate a carbocation, which is known as a heterolysis step. In the second step, a base removes a proton, forming an alkene. The free energy diagram is a plot of free energy vs reaction coordinates. As E1 reaction occurs in two steps, there are two transition states with one intermediate which supports the mechanism. The overall reactants are shown on the far left; the overall products are shown on the far right, and the intermediates appear at the local energy minimum in between.

Answer 10

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Answer 11

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Answer 13

Ch. 8 - Prob. 8.1P Ch. 8 - Prob. 8.2P Ch. 8 - Prob. 8.3P Ch. 8 - Prob. 8.4P Ch. 8 - Prob. 8.5P Ch. 8 - Prob. 8.6P Ch. 8 - Prob. 8.7P Ch. 8 - Prob. 8.8P Ch. 8 - Prob. 8.9P Ch. 8 - Prob. 8.10P

Solution Summary: The author describes the E1 reaction as a unimolecular elimination reaction that takes place in two steps.

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