(a) Interpretation: The iodo (–I) and formyl (–CHO) groups are not listed in Table 23-1. The relative amounts of ortho and meta nitration products obtained for each substituent are shown here: The missing information pertaining to the relative amounts of the para isomers that are produced as well as the sum of the amounts of ortho and para products are to be supplied. Concept introduction: The substituent on the benzene ring prior to substitution dictates the regiochemistry of the reaction. Some substituents are designated as ortho/para directors because they lead to product mixtures consisting primarily of the ortho- and para-disubstituted products. Other substituents are designated as meta directors because they favor the formation of the meta-disubstituted product. The results from nitration reactions are summarized in Table 23-1:

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Answer 1

Question

Chapter 23, Problem 23.1YT

Interpretation Introduction

(a)

Interpretation:

The iodo (–I) and formyl (–CHO) groups are not listed in Table 23-1. The relative amounts of ortho and meta nitration products obtained for each substituent are shown here:

The missing information pertaining to the relative amounts of the para isomers that are produced as well as the sum of the amounts of ortho and para products are to be supplied.

Concept introduction:

The substituent on the benzene ring prior to substitution dictates the regiochemistry of the reaction. Some substituents are designated as ortho/para directors because they lead to product mixtures consisting primarily of the ortho- and para-disubstituted products. Other substituents are designated as meta directors because they favor the formation of the meta-disubstituted product. The results from nitration reactions are summarized in Table 23-1:

Interpretation Introduction

(b)

Interpretation:

The iodo (–I) and formyl (–CHO) groups are not listed in Table 23-1. The relative amounts of ortho and meta nitration products obtained for each substituent are shown here:

Based on the information, whether each substituent is an ortho/para director or a meta director is to be determined.

Concept introduction:

The substituent on the benzene ring prior to substitution dictates the regiochemistry of the reaction. Some substituents are designated as ortho/para directors because they lead to product mixtures consisting primarily of the ortho- and para-disubstituted products. Other substituents are designated as meta directors because they favor the formation of the meta-disubstituted product. The results from nitration reactions are summarized in Table 23-1:

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2. Provide a clear arrow-pushing mechanism for the following reactions. Do not skip proton transfers, do not combine steps, and make sure your arrows are clear enough to be interpreted without ambiguity. a. CH3 Ph OEt هد Ph CH3 Hint: the species on the left is an ynolate, which behaves a lot like an enolate.

b. CH3 H3C CH3 CH3 H3C an unexpected product, containing a single 9- membered ring the expected product, containing two fused rings H3C-I (H3C)2CuLi an enolate

Answer 2

Question

Chapter 23, Problem 23.1YT

Interpretation Introduction

(a)

Interpretation:

The iodo (–I) and formyl (–CHO) groups are not listed in Table 23-1. The relative amounts of ortho and meta nitration products obtained for each substituent are shown here:

The missing information pertaining to the relative amounts of the para isomers that are produced as well as the sum of the amounts of ortho and para products are to be supplied.

Concept introduction:

The substituent on the benzene ring prior to substitution dictates the regiochemistry of the reaction. Some substituents are designated as ortho/para directors because they lead to product mixtures consisting primarily of the ortho- and para-disubstituted products. Other substituents are designated as meta directors because they favor the formation of the meta-disubstituted product. The results from nitration reactions are summarized in Table 23-1:

Interpretation Introduction

(b)

Interpretation:

The iodo (–I) and formyl (–CHO) groups are not listed in Table 23-1. The relative amounts of ortho and meta nitration products obtained for each substituent are shown here:

Based on the information, whether each substituent is an ortho/para director or a meta director is to be determined.

Concept introduction:

The substituent on the benzene ring prior to substitution dictates the regiochemistry of the reaction. Some substituents are designated as ortho/para directors because they lead to product mixtures consisting primarily of the ortho- and para-disubstituted products. Other substituents are designated as meta directors because they favor the formation of the meta-disubstituted product. The results from nitration reactions are summarized in Table 23-1:

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Answer 3

Question

Chapter 23, Problem 23.1YT

Interpretation Introduction

(a)

Interpretation:

The iodo (–I) and formyl (–CHO) groups are not listed in Table 23-1. The relative amounts of ortho and meta nitration products obtained for each substituent are shown here:

The missing information pertaining to the relative amounts of the para isomers that are produced as well as the sum of the amounts of ortho and para products are to be supplied.

Concept introduction:

The substituent on the benzene ring prior to substitution dictates the regiochemistry of the reaction. Some substituents are designated as ortho/para directors because they lead to product mixtures consisting primarily of the ortho- and para-disubstituted products. Other substituents are designated as meta directors because they favor the formation of the meta-disubstituted product. The results from nitration reactions are summarized in Table 23-1:

Interpretation Introduction

(b)

Interpretation:

The iodo (–I) and formyl (–CHO) groups are not listed in Table 23-1. The relative amounts of ortho and meta nitration products obtained for each substituent are shown here:

Based on the information, whether each substituent is an ortho/para director or a meta director is to be determined.

Concept introduction:

The substituent on the benzene ring prior to substitution dictates the regiochemistry of the reaction. Some substituents are designated as ortho/para directors because they lead to product mixtures consisting primarily of the ortho- and para-disubstituted products. Other substituents are designated as meta directors because they favor the formation of the meta-disubstituted product. The results from nitration reactions are summarized in Table 23-1:

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Answer 4

Question

Chapter 23, Problem 23.1YT

Interpretation Introduction

(a)

Interpretation:

The iodo (–I) and formyl (–CHO) groups are not listed in Table 23-1. The relative amounts of ortho and meta nitration products obtained for each substituent are shown here:

The missing information pertaining to the relative amounts of the para isomers that are produced as well as the sum of the amounts of ortho and para products are to be supplied.

Concept introduction:

The substituent on the benzene ring prior to substitution dictates the regiochemistry of the reaction. Some substituents are designated as ortho/para directors because they lead to product mixtures consisting primarily of the ortho- and para-disubstituted products. Other substituents are designated as meta directors because they favor the formation of the meta-disubstituted product. The results from nitration reactions are summarized in Table 23-1:

Interpretation Introduction

(b)

Interpretation:

The iodo (–I) and formyl (–CHO) groups are not listed in Table 23-1. The relative amounts of ortho and meta nitration products obtained for each substituent are shown here:

Based on the information, whether each substituent is an ortho/para director or a meta director is to be determined.

Concept introduction:

The substituent on the benzene ring prior to substitution dictates the regiochemistry of the reaction. Some substituents are designated as ortho/para directors because they lead to product mixtures consisting primarily of the ortho- and para-disubstituted products. Other substituents are designated as meta directors because they favor the formation of the meta-disubstituted product. The results from nitration reactions are summarized in Table 23-1:

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Answer 5

Chapter 23, Problem 23.1YT

Interpretation Introduction

(a)

Interpretation:

The iodo (–I) and formyl (–CHO) groups are not listed in Table 23-1. The relative amounts of ortho and meta nitration products obtained for each substituent are shown here:

The missing information pertaining to the relative amounts of the para isomers that are produced as well as the sum of the amounts of ortho and para products are to be supplied.

Concept introduction:

The substituent on the benzene ring prior to substitution dictates the regiochemistry of the reaction. Some substituents are designated as ortho/para directors because they lead to product mixtures consisting primarily of the ortho- and para-disubstituted products. Other substituents are designated as meta directors because they favor the formation of the meta-disubstituted product. The results from nitration reactions are summarized in Table 23-1:

Interpretation Introduction

(b)

Interpretation:

The iodo (–I) and formyl (–CHO) groups are not listed in Table 23-1. The relative amounts of ortho and meta nitration products obtained for each substituent are shown here:

Based on the information, whether each substituent is an ortho/para director or a meta director is to be determined.

Concept introduction:

The substituent on the benzene ring prior to substitution dictates the regiochemistry of the reaction. Some substituents are designated as ortho/para directors because they lead to product mixtures consisting primarily of the ortho- and para-disubstituted products. Other substituents are designated as meta directors because they favor the formation of the meta-disubstituted product. The results from nitration reactions are summarized in Table 23-1:

Answer 6

Chapter 23, Problem 23.1YT

Interpretation Introduction

(a)

Interpretation:

The iodo (–I) and formyl (–CHO) groups are not listed in Table 23-1. The relative amounts of ortho and meta nitration products obtained for each substituent are shown here:

The missing information pertaining to the relative amounts of the para isomers that are produced as well as the sum of the amounts of ortho and para products are to be supplied.

Concept introduction:

The substituent on the benzene ring prior to substitution dictates the regiochemistry of the reaction. Some substituents are designated as ortho/para directors because they lead to product mixtures consisting primarily of the ortho- and para-disubstituted products. Other substituents are designated as meta directors because they favor the formation of the meta-disubstituted product. The results from nitration reactions are summarized in Table 23-1:

Answer 7

Chapter 23, Problem 23.1YT

Interpretation Introduction

(a)

Interpretation:

The iodo (–I) and formyl (–CHO) groups are not listed in Table 23-1. The relative amounts of ortho and meta nitration products obtained for each substituent are shown here:

The missing information pertaining to the relative amounts of the para isomers that are produced as well as the sum of the amounts of ortho and para products are to be supplied.

Concept introduction:

The substituent on the benzene ring prior to substitution dictates the regiochemistry of the reaction. Some substituents are designated as ortho/para directors because they lead to product mixtures consisting primarily of the ortho- and para-disubstituted products. Other substituents are designated as meta directors because they favor the formation of the meta-disubstituted product. The results from nitration reactions are summarized in Table 23-1:

Answer 8

Interpretation Introduction

(b)

Interpretation:

The iodo (–I) and formyl (–CHO) groups are not listed in Table 23-1. The relative amounts of ortho and meta nitration products obtained for each substituent are shown here:

Based on the information, whether each substituent is an ortho/para director or a meta director is to be determined.

Concept introduction:

The substituent on the benzene ring prior to substitution dictates the regiochemistry of the reaction. Some substituents are designated as ortho/para directors because they lead to product mixtures consisting primarily of the ortho- and para-disubstituted products. Other substituents are designated as meta directors because they favor the formation of the meta-disubstituted product. The results from nitration reactions are summarized in Table 23-1:

Answer 9

Interpretation Introduction

(b)

Interpretation:

The iodo (–I) and formyl (–CHO) groups are not listed in Table 23-1. The relative amounts of ortho and meta nitration products obtained for each substituent are shown here:

Based on the information, whether each substituent is an ortho/para director or a meta director is to be determined.

Concept introduction:

The substituent on the benzene ring prior to substitution dictates the regiochemistry of the reaction. Some substituents are designated as ortho/para directors because they lead to product mixtures consisting primarily of the ortho- and para-disubstituted products. Other substituents are designated as meta directors because they favor the formation of the meta-disubstituted product. The results from nitration reactions are summarized in Table 23-1:

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 23 - Prob. 23.1P Ch. 23 - Prob. 23.2P Ch. 23 - Prob. 23.3P Ch. 23 - Prob. 23.4P Ch. 23 - Prob. 23.5P Ch. 23 - Prob. 23.6P Ch. 23 - Prob. 23.7P Ch. 23 - Prob. 23.8P Ch. 23 - Prob. 23.9P Ch. 23 - Prob. 23.10P

Solution Summary: The iodo and formyl groups are not listed in Table 23-1. The relative amounts of para isomers and the sum of the ortho and para products are shown.

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Chapter 23 Solutions