a) Interpretation: To explain the Hofmann elimination of the given amines . Concept introduction: The Hofmann elimination is an E2 reaction that converts an amine into an alkene and occurs with a non-zaitsev stereo chemistry to form the less highly substituted double bond. To predict the product, we look at the reactant and identify the position from which elimination might occur (the positions two carbons away from nitrogen) then carry out an elimination using the most accessible hydrogen. In the present instance, the hydrogens on C â€“ 3 are far away from the quaternary ammonium ion N + (CH 3 ). The C â€“ 3 hydrogen are less hindered and more accessible to the base â€“ OH.

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Answer 1

Question

Chapter 24.7, Problem 14P

Interpretation Introduction

a)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

The Hofmann elimination is an E2 reaction that converts an amine into an alkene and occurs with a non-zaitsev stereo chemistry to form the less highly substituted double bond. To predict the product, we look at the reactant and identify the position from which elimination might occur (the positions two carbons away from nitrogen) then carry out an elimination using the most accessible hydrogen. In the present instance, the hydrogens on C â€“ 3 are far away from the quaternary ammonium ion N⁺ (CH₃). The C â€“ 3 hydrogen are less hindered and more accessible to the base ^â€“OH.

Interpretation Introduction

b)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

Just like alcohol, amines can be converted into alkenes by an elimination reaction.

But because an amide ion, ^-NH₂ is a poor leaving group, it must be converted into a better leaving group.

Interpretation Introduction

c)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

The given amine has two symmetrical groups is CH₃CH₂CH₂ â€“ attached to the carbon C-4- carrying the amine ^â€“NH₂ group.

Interpretation Introduction

d)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

The Hofmann elimination is an E2 elimination that converts an amine to an alkene and occurs with non-Zaitsev regiochemistry to form the less highly substituted double bond alkene as the major product.

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3. SYNTHESIS. Propose a sequence of synthetic steps (FGI) that convert the starting material (SM) into the Target molecule. For each FGI in your proposed synthesis, specify the reagents / conditions, and draw the product(s) of that FGI. DO NOT INCLUDE the FGI mxn in the answer you submit. If an FGI requires two reagent sets, specify the order in which the reagent sets are added, e.g., i) Hg(OAc)2 / H₂O; ii) NaBH4/MeOH. Indicate the stereochemistry (if any) of the products of each FGI. FGI 1. Me Starting Material Source of all carbons in the Target molecule (can use multiple copies) Me Me Target molecule + enantiomer

curved arrows are used to illustate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction mechanism steps

Answer 2

Question

Chapter 24.7, Problem 14P

Interpretation Introduction

a)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

The Hofmann elimination is an E2 reaction that converts an amine into an alkene and occurs with a non-zaitsev stereo chemistry to form the less highly substituted double bond. To predict the product, we look at the reactant and identify the position from which elimination might occur (the positions two carbons away from nitrogen) then carry out an elimination using the most accessible hydrogen. In the present instance, the hydrogens on C â€“ 3 are far away from the quaternary ammonium ion N⁺ (CH₃). The C â€“ 3 hydrogen are less hindered and more accessible to the base ^â€“OH.

Interpretation Introduction

b)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

Just like alcohol, amines can be converted into alkenes by an elimination reaction.

But because an amide ion, ^-NH₂ is a poor leaving group, it must be converted into a better leaving group.

Interpretation Introduction

c)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

The given amine has two symmetrical groups is CH₃CH₂CH₂ â€“ attached to the carbon C-4- carrying the amine ^â€“NH₂ group.

Interpretation Introduction

d)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

The Hofmann elimination is an E2 elimination that converts an amine to an alkene and occurs with non-Zaitsev regiochemistry to form the less highly substituted double bond alkene as the major product.

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Answer 3

Question

Chapter 24.7, Problem 14P

Interpretation Introduction

a)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

The Hofmann elimination is an E2 reaction that converts an amine into an alkene and occurs with a non-zaitsev stereo chemistry to form the less highly substituted double bond. To predict the product, we look at the reactant and identify the position from which elimination might occur (the positions two carbons away from nitrogen) then carry out an elimination using the most accessible hydrogen. In the present instance, the hydrogens on C â€“ 3 are far away from the quaternary ammonium ion N⁺ (CH₃). The C â€“ 3 hydrogen are less hindered and more accessible to the base ^â€“OH.

Interpretation Introduction

b)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

Just like alcohol, amines can be converted into alkenes by an elimination reaction.

But because an amide ion, ^-NH₂ is a poor leaving group, it must be converted into a better leaving group.

Interpretation Introduction

c)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

The given amine has two symmetrical groups is CH₃CH₂CH₂ â€“ attached to the carbon C-4- carrying the amine ^â€“NH₂ group.

Interpretation Introduction

d)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

The Hofmann elimination is an E2 elimination that converts an amine to an alkene and occurs with non-Zaitsev regiochemistry to form the less highly substituted double bond alkene as the major product.

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Answer 4

Question

Chapter 24.7, Problem 14P

Interpretation Introduction

a)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

The Hofmann elimination is an E2 reaction that converts an amine into an alkene and occurs with a non-zaitsev stereo chemistry to form the less highly substituted double bond. To predict the product, we look at the reactant and identify the position from which elimination might occur (the positions two carbons away from nitrogen) then carry out an elimination using the most accessible hydrogen. In the present instance, the hydrogens on C â€“ 3 are far away from the quaternary ammonium ion N⁺ (CH₃). The C â€“ 3 hydrogen are less hindered and more accessible to the base ^â€“OH.

Interpretation Introduction

b)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

Just like alcohol, amines can be converted into alkenes by an elimination reaction.

But because an amide ion, ^-NH₂ is a poor leaving group, it must be converted into a better leaving group.

Interpretation Introduction

c)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

The given amine has two symmetrical groups is CH₃CH₂CH₂ â€“ attached to the carbon C-4- carrying the amine ^â€“NH₂ group.

Interpretation Introduction

d)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

The Hofmann elimination is an E2 elimination that converts an amine to an alkene and occurs with non-Zaitsev regiochemistry to form the less highly substituted double bond alkene as the major product.

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Answer 5

Chapter 24.7, Problem 14P

Interpretation Introduction

a)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

The Hofmann elimination is an E2 reaction that converts an amine into an alkene and occurs with a non-zaitsev stereo chemistry to form the less highly substituted double bond. To predict the product, we look at the reactant and identify the position from which elimination might occur (the positions two carbons away from nitrogen) then carry out an elimination using the most accessible hydrogen. In the present instance, the hydrogens on C â€“ 3 are far away from the quaternary ammonium ion N⁺ (CH₃). The C â€“ 3 hydrogen are less hindered and more accessible to the base ^â€“OH.

Interpretation Introduction

b)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

Just like alcohol, amines can be converted into alkenes by an elimination reaction.

But because an amide ion, ^-NH₂ is a poor leaving group, it must be converted into a better leaving group.

Interpretation Introduction

c)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

The given amine has two symmetrical groups is CH₃CH₂CH₂ â€“ attached to the carbon C-4- carrying the amine ^â€“NH₂ group.

Interpretation Introduction

d)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

The Hofmann elimination is an E2 elimination that converts an amine to an alkene and occurs with non-Zaitsev regiochemistry to form the less highly substituted double bond alkene as the major product.

Answer 6

Chapter 24.7, Problem 14P

Interpretation Introduction

a)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

The Hofmann elimination is an E2 reaction that converts an amine into an alkene and occurs with a non-zaitsev stereo chemistry to form the less highly substituted double bond. To predict the product, we look at the reactant and identify the position from which elimination might occur (the positions two carbons away from nitrogen) then carry out an elimination using the most accessible hydrogen. In the present instance, the hydrogens on C â€“ 3 are far away from the quaternary ammonium ion N⁺ (CH₃). The C â€“ 3 hydrogen are less hindered and more accessible to the base ^â€“OH.

Answer 7

Chapter 24.7, Problem 14P

Interpretation Introduction

a)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

The Hofmann elimination is an E2 reaction that converts an amine into an alkene and occurs with a non-zaitsev stereo chemistry to form the less highly substituted double bond. To predict the product, we look at the reactant and identify the position from which elimination might occur (the positions two carbons away from nitrogen) then carry out an elimination using the most accessible hydrogen. In the present instance, the hydrogens on C â€“ 3 are far away from the quaternary ammonium ion N⁺ (CH₃). The C â€“ 3 hydrogen are less hindered and more accessible to the base ^â€“OH.

Answer 8

Interpretation Introduction

b)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

Just like alcohol, amines can be converted into alkenes by an elimination reaction.

But because an amide ion, ^-NH₂ is a poor leaving group, it must be converted into a better leaving group.

Answer 9

Interpretation Introduction

b)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

Just like alcohol, amines can be converted into alkenes by an elimination reaction.

But because an amide ion, ^-NH₂ is a poor leaving group, it must be converted into a better leaving group.

Answer 10

Interpretation Introduction

c)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

The given amine has two symmetrical groups is CH₃CH₂CH₂ â€“ attached to the carbon C-4- carrying the amine ^â€“NH₂ group.

Answer 11

Interpretation Introduction

c)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

The given amine has two symmetrical groups is CH₃CH₂CH₂ â€“ attached to the carbon C-4- carrying the amine ^â€“NH₂ group.

Answer 12

Interpretation Introduction

d)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

The Hofmann elimination is an E2 elimination that converts an amine to an alkene and occurs with non-Zaitsev regiochemistry to form the less highly substituted double bond alkene as the major product.

Answer 13

Interpretation Introduction

d)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

The Hofmann elimination is an E2 elimination that converts an amine to an alkene and occurs with non-Zaitsev regiochemistry to form the less highly substituted double bond alkene as the major product.

Answer 14

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Answer 25

Ch. 24.1 - Name the following compounds:Ch. 24.1 - Prob. 2P Ch. 24.1 - Prob. 3P Ch. 24.3 - Prob. 4P Ch. 24.3 - The benzylammonium ion (C6H5CH2NH3+) has pKa =...Ch. 24.4 - Prob. 6P Ch. 24.5 - Prob. 7P Ch. 24.6 - Prob. 8P Ch. 24.6 - Prob. 9P Ch. 24.6 - Show two methods for the synthesis of dopamine, a...

Solution Summary: The author explains the Hofmann elimination reaction, which converts an amine into an alkene and occurs with a non-zaitsev stereo chemistry.

b)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

Just like alcohol, amines can be converted into alkenes by an elimination reaction.

But because an amide ion, ^-NH₂ is a poor leaving group, it must be converted into a better leaving group.

c)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

The given amine has two symmetrical groups is CH₃CH₂CH₂ â€“ attached to the carbon C-4- carrying the amine ^â€“NH₂ group.

Chapter 24 Solutions

Solution Summary: The author explains the Hofmann elimination reaction, which converts an amine into an alkene and occurs with a non-zaitsev stereo chemistry.

b) Interpretation: To explain the Hofmann elimination of the given amines. Concept introduction: Just like alcohol, amines can be converted into alkenes by an elimination reaction. But because an amide ion, -NH2 is a poor leaving group, it must be converted into a better leaving group.

c) Interpretation: To explain the Hofmann elimination of the given amines. Concept introduction: The given amine has two symmetrical groups is CH3CH2CH2 â€“ attached to the carbon C-4- carrying the amine â€“NH2 group.

d) Interpretation: To explain the Hofmann elimination of the given amines. Concept introduction: The Hofmann elimination is an E2 elimination that converts an amine to an alkene and occurs with non-Zaitsev regiochemistry to form the less highly substituted double bond alkene as the major product.

Chapter 24 Solutions

b)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

Just like alcohol, amines can be converted into alkenes by an elimination reaction.

But because an amide ion, ^-NH₂ is a poor leaving group, it must be converted into a better leaving group.

c)

Interpretation:

To explain the Hofmann elimination of the given amines.

Concept introduction:

The given amine has two symmetrical groups is CH₃CH₂CH₂ â€“ attached to the carbon C-4- carrying the amine ^â€“NH₂ group.