(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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יווי 10 20 30 40 50 60 70 3.5 3 2.5 2 1.5 1 [ppm] 3.5 3 2.5 2 1.5 1 6 [ppm] 1 1.5 -2.5 3.5

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Part VII. Below are the 'HNMR, 13 C-NMR, COSY 2D- NMR, and HSQC 2D-NMR (similar with HETCOR but axes are reversed) spectra of an organic compound with molecular formula C6H1003 - Assign chemical shift values to the H and c atoms of the compound. Find the structure. Show complete solutions. Predicted 1H NMR Spectrum 4.7 4.6 4.5 4.4 4.3 4.2 4.1 4.0 3.9 3.8 3.7 3.6 3.5 3.4 3.3 3.2 3.1 3.0 2.9 2.8 2.7 2.6 2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1 f1 (ppm) Predicted 13C NMR Spectrum 100 f1 (ppm) 30 220 210 200 190 180 170 160 150 140 130 120 110 90 80 70 -26 60 50 40 46 30 20 115 10 1.0 0.9 0.8 0 -10

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