(a) Interpretation: A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written. Concept introduction: Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow ( → ) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step. Alkene to amine is a retrosynthethic approach of Hofmann elimination reaction. The Hofmann elimination reaction leads to an anti-Zaitsev elimination product or Hofmann product. An amine with a poor leaving group is converted into a tetraalkyl ammonium ion, which has a moderately good leaving group, using excess of an alkyl halide like CH 3 I . Subsequent treatment with Ag 2 O , followed by heat, induces elimination.

Question

Rank each of the following substituted benzene molecules in order of which will react fastest (1) to slowest (4) by electrophilic aromatic substitution. Explanation Check Х (Choose one) OH (Choose one) OCH3 (Choose one) OH (Choose one) © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center

Answer 1

Question

Chapter 13, Problem 13.31P

Interpretation Introduction

(a)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Alkene to amine is a retrosynthethic approach of Hofmann elimination reaction.

The Hofmann elimination reaction leads to an anti-Zaitsev elimination product or Hofmann product. An amine with a poor leaving group is converted into a tetraalkyl ammonium ion, which has a moderately good leaving group, using excess of an alkyl halide like CH3I. Subsequent treatment with Ag2O, followed by heat, induces elimination.

Interpretation Introduction

(b)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Reaction with LDA leads to alkylation at the less highly alkyl substituted carbon atom.

Interpretation Introduction

(c)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Esterification is the reaction of acid with diazomethane to form the desired ester as a product.

Interpretation Introduction

(d)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Most hydrogen halide reactions with alkynes occur in a Markovnikov-manner in which the halide attaches to the most substituted carbon.

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Answer 2

Question

Chapter 13, Problem 13.31P

Interpretation Introduction

(a)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Alkene to amine is a retrosynthethic approach of Hofmann elimination reaction.

The Hofmann elimination reaction leads to an anti-Zaitsev elimination product or Hofmann product. An amine with a poor leaving group is converted into a tetraalkyl ammonium ion, which has a moderately good leaving group, using excess of an alkyl halide like CH3I. Subsequent treatment with Ag2O, followed by heat, induces elimination.

Interpretation Introduction

(b)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Reaction with LDA leads to alkylation at the less highly alkyl substituted carbon atom.

Interpretation Introduction

(c)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Esterification is the reaction of acid with diazomethane to form the desired ester as a product.

Interpretation Introduction

(d)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Most hydrogen halide reactions with alkynes occur in a Markovnikov-manner in which the halide attaches to the most substituted carbon.

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Answer 3

Question

Chapter 13, Problem 13.31P

Interpretation Introduction

(a)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Alkene to amine is a retrosynthethic approach of Hofmann elimination reaction.

The Hofmann elimination reaction leads to an anti-Zaitsev elimination product or Hofmann product. An amine with a poor leaving group is converted into a tetraalkyl ammonium ion, which has a moderately good leaving group, using excess of an alkyl halide like CH3I. Subsequent treatment with Ag2O, followed by heat, induces elimination.

Interpretation Introduction

(b)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Reaction with LDA leads to alkylation at the less highly alkyl substituted carbon atom.

Interpretation Introduction

(c)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Esterification is the reaction of acid with diazomethane to form the desired ester as a product.

Interpretation Introduction

(d)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Most hydrogen halide reactions with alkynes occur in a Markovnikov-manner in which the halide attaches to the most substituted carbon.

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Answer 4

Question

Chapter 13, Problem 13.31P

Interpretation Introduction

(a)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Alkene to amine is a retrosynthethic approach of Hofmann elimination reaction.

The Hofmann elimination reaction leads to an anti-Zaitsev elimination product or Hofmann product. An amine with a poor leaving group is converted into a tetraalkyl ammonium ion, which has a moderately good leaving group, using excess of an alkyl halide like CH3I. Subsequent treatment with Ag2O, followed by heat, induces elimination.

Interpretation Introduction

(b)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Reaction with LDA leads to alkylation at the less highly alkyl substituted carbon atom.

Interpretation Introduction

(c)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Esterification is the reaction of acid with diazomethane to form the desired ester as a product.

Interpretation Introduction

(d)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Most hydrogen halide reactions with alkynes occur in a Markovnikov-manner in which the halide attaches to the most substituted carbon.

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Answer 5

Chapter 13, Problem 13.31P

Interpretation Introduction

(a)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Alkene to amine is a retrosynthethic approach of Hofmann elimination reaction.

The Hofmann elimination reaction leads to an anti-Zaitsev elimination product or Hofmann product. An amine with a poor leaving group is converted into a tetraalkyl ammonium ion, which has a moderately good leaving group, using excess of an alkyl halide like CH3I. Subsequent treatment with Ag2O, followed by heat, induces elimination.

Interpretation Introduction

(b)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Reaction with LDA leads to alkylation at the less highly alkyl substituted carbon atom.

Interpretation Introduction

(c)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Esterification is the reaction of acid with diazomethane to form the desired ester as a product.

Interpretation Introduction

(d)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Most hydrogen halide reactions with alkynes occur in a Markovnikov-manner in which the halide attaches to the most substituted carbon.

Answer 6

Chapter 13, Problem 13.31P

Interpretation Introduction

(a)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Alkene to amine is a retrosynthethic approach of Hofmann elimination reaction.

The Hofmann elimination reaction leads to an anti-Zaitsev elimination product or Hofmann product. An amine with a poor leaving group is converted into a tetraalkyl ammonium ion, which has a moderately good leaving group, using excess of an alkyl halide like CH3I. Subsequent treatment with Ag2O, followed by heat, induces elimination.

Answer 7

Chapter 13, Problem 13.31P

Interpretation Introduction

(a)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Alkene to amine is a retrosynthethic approach of Hofmann elimination reaction.

The Hofmann elimination reaction leads to an anti-Zaitsev elimination product or Hofmann product. An amine with a poor leaving group is converted into a tetraalkyl ammonium ion, which has a moderately good leaving group, using excess of an alkyl halide like CH3I. Subsequent treatment with Ag2O, followed by heat, induces elimination.

Answer 8

Interpretation Introduction

(b)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Reaction with LDA leads to alkylation at the less highly alkyl substituted carbon atom.

Answer 9

Interpretation Introduction

(b)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Reaction with LDA leads to alkylation at the less highly alkyl substituted carbon atom.

Answer 10

Interpretation Introduction

(c)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Esterification is the reaction of acid with diazomethane to form the desired ester as a product.

Answer 11

Interpretation Introduction

(c)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Esterification is the reaction of acid with diazomethane to form the desired ester as a product.

Answer 12

Interpretation Introduction

(d)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Most hydrogen halide reactions with alkynes occur in a Markovnikov-manner in which the halide attaches to the most substituted carbon.

Answer 13

Interpretation Introduction

(d)

Interpretation:

A synthetic step for the given transformation, including reagents and special reaction conditions in the forward direction, is to be written.

Concept introduction:

Synthesis may be designed by thinking in the reverse direction, from the product to the starting compound, in a method called retrosynthesis. A synthesis is a specific sequence of chemical reactions that converts the starting materials into the desired compound, called the target (or synthetic target). The product given in the retrosynthetic step is the precursor for the synthetic step, followed by an arrow (→) with reaction conditions and the product (precursor in the retrosynthetic step) is the synthetic step.

Most hydrogen halide reactions with alkynes occur in a Markovnikov-manner in which the halide attaches to the most substituted carbon.

Answer 14

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Answer 25

Ch. 13 - Prob. 13.1P Ch. 13 - Prob. 13.2P Ch. 13 - Prob. 13.3P Ch. 13 - Prob. 13.4P Ch. 13 - Prob. 13.5P Ch. 13 - Prob. 13.6P Ch. 13 - Prob. 13.7P Ch. 13 - Prob. 13.8P Ch. 13 - Prob. 13.9P Ch. 13 - Prob. 13.10P

Solution Summary: The author explains that a synthetic step for the given transformation, including reagents and special reaction conditions, is to be written.

Chapter 13 Solutions