a) Interpretation: Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2-bromo-4-nitrotoluene can be synthesized is to be stated. Concept introduction: In aromatic electrophilic substitution reactions halogens and methyl group are ortho and para directing groups while the nitro group is a meta directing group. Hence to prepare 2-bromo-4-nitrotoluene, toluene has to be halogenated and the chlorotoluene obtained should be nitrated. Electrophilic substitution of di and trisubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons. To state: Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2-bromo-4-nitrotoluene can be synthesized.

Question

For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. ? NH2 MgBr Will the first product that forms in this reaction create a new CC bond? ○ Yes ○ No MgBr ? Will the first product that forms in this reaction create a new CC bond? O Yes O No Click and drag to start drawing a structure. :☐ G x c olo Ar HE

Answer 1

Question

Chapter 16.SE, Problem 57AP

Interpretation Introduction

a)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2-bromo-4-nitrotoluene can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens and methyl group are ortho and para directing groups while the nitro group is a meta directing group. Hence to prepare 2-bromo-4-nitrotoluene, toluene has to be halogenated and the chlorotoluene obtained should be nitrated.

Electrophilic substitution of di and trisubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2-bromo-4-nitrotoluene can be synthesized.

Interpretation Introduction

b)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 1,3,5-trinitrobenzene can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions the nitro group is a meta directing group. Nitration of benzene gives nitrobenzene. Further nitration of nitrobenzene will introduce nitro groups into the two meta positions to yield the trinitro compound.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 1,3,5-trinitrobenzene can be synthesized.

Interpretation Introduction

c)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2,4,6-tribromoaniline can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, the amino group is an ortho and para directing group. Nitration of benzene gives nitrobenzene. Nitrobenzene can be reduced to aminobenzene (aniline). Aniline upon bromoination will yield 2,4,6-tribromoaniline.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2,4,6-tribromoaniline can be synthesized.

Interpretation Introduction

d)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how m-fluorobenzoic acid can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions the carboxylic acid group is a meta directing group. Hence to prepare m- fluorobenzoic acid, benzene should be first converted into benzoicacid. Direct fluorination of aromatic rings is not possible as fluorine is too reactive and it is not possible to stop the reaction at the monofluorinated stage. Fluorination is normally carried out using F-TEDA-BF₄ which has a fluorine atom bonded to positively charged nitrogen.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how m-fluorobenzoic acid can be synthesized.

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For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. ? NH2 MgBr Will the first product that forms in this reaction create a new CC bond? ○ Yes ○ No MgBr ? Will the first product that forms in this reaction create a new CC bond? O Yes O No Click and drag to start drawing a structure. :☐ G x c olo Ar HE

Predicting As the lead product manager at OrganometALEKS Industries, you are trying to decide if the following reaction will make a molecule with a new C - C bond as its major product: H₂N O H 1. ? 2. H3O+ If this reaction will work, draw the major organic product or products you would expect in the drawing area below. If there's more than one major product, you can draw them in any arrangement you like. Be sure you use wedge and dash bonds if necessary, for example to distinguish between major products with different stereochemistry. 0 If the major products of this reaction won't have a new CC bond, just check the box under the drawing area and leave it blank. فا Explanation Check Click and drag to start drawing a structure.

Highlight the chirality (or stereogenic) center(s) in the given compound. A compound may have one or more stereogenic centers. OH OH OH OH OH OH

Answer 2

Question

Chapter 16.SE, Problem 57AP

Interpretation Introduction

a)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2-bromo-4-nitrotoluene can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens and methyl group are ortho and para directing groups while the nitro group is a meta directing group. Hence to prepare 2-bromo-4-nitrotoluene, toluene has to be halogenated and the chlorotoluene obtained should be nitrated.

Electrophilic substitution of di and trisubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2-bromo-4-nitrotoluene can be synthesized.

Interpretation Introduction

b)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 1,3,5-trinitrobenzene can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions the nitro group is a meta directing group. Nitration of benzene gives nitrobenzene. Further nitration of nitrobenzene will introduce nitro groups into the two meta positions to yield the trinitro compound.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 1,3,5-trinitrobenzene can be synthesized.

Interpretation Introduction

c)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2,4,6-tribromoaniline can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, the amino group is an ortho and para directing group. Nitration of benzene gives nitrobenzene. Nitrobenzene can be reduced to aminobenzene (aniline). Aniline upon bromoination will yield 2,4,6-tribromoaniline.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2,4,6-tribromoaniline can be synthesized.

Interpretation Introduction

d)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how m-fluorobenzoic acid can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions the carboxylic acid group is a meta directing group. Hence to prepare m- fluorobenzoic acid, benzene should be first converted into benzoicacid. Direct fluorination of aromatic rings is not possible as fluorine is too reactive and it is not possible to stop the reaction at the monofluorinated stage. Fluorination is normally carried out using F-TEDA-BF₄ which has a fluorine atom bonded to positively charged nitrogen.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how m-fluorobenzoic acid can be synthesized.

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Answer 3

Question

Chapter 16.SE, Problem 57AP

Interpretation Introduction

a)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2-bromo-4-nitrotoluene can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens and methyl group are ortho and para directing groups while the nitro group is a meta directing group. Hence to prepare 2-bromo-4-nitrotoluene, toluene has to be halogenated and the chlorotoluene obtained should be nitrated.

Electrophilic substitution of di and trisubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2-bromo-4-nitrotoluene can be synthesized.

Interpretation Introduction

b)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 1,3,5-trinitrobenzene can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions the nitro group is a meta directing group. Nitration of benzene gives nitrobenzene. Further nitration of nitrobenzene will introduce nitro groups into the two meta positions to yield the trinitro compound.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 1,3,5-trinitrobenzene can be synthesized.

Interpretation Introduction

c)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2,4,6-tribromoaniline can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, the amino group is an ortho and para directing group. Nitration of benzene gives nitrobenzene. Nitrobenzene can be reduced to aminobenzene (aniline). Aniline upon bromoination will yield 2,4,6-tribromoaniline.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2,4,6-tribromoaniline can be synthesized.

Interpretation Introduction

d)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how m-fluorobenzoic acid can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions the carboxylic acid group is a meta directing group. Hence to prepare m- fluorobenzoic acid, benzene should be first converted into benzoicacid. Direct fluorination of aromatic rings is not possible as fluorine is too reactive and it is not possible to stop the reaction at the monofluorinated stage. Fluorination is normally carried out using F-TEDA-BF₄ which has a fluorine atom bonded to positively charged nitrogen.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how m-fluorobenzoic acid can be synthesized.

Expert Solution & Answer

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Answer 4

Question

Chapter 16.SE, Problem 57AP

Interpretation Introduction

a)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2-bromo-4-nitrotoluene can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens and methyl group are ortho and para directing groups while the nitro group is a meta directing group. Hence to prepare 2-bromo-4-nitrotoluene, toluene has to be halogenated and the chlorotoluene obtained should be nitrated.

Electrophilic substitution of di and trisubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2-bromo-4-nitrotoluene can be synthesized.

Interpretation Introduction

b)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 1,3,5-trinitrobenzene can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions the nitro group is a meta directing group. Nitration of benzene gives nitrobenzene. Further nitration of nitrobenzene will introduce nitro groups into the two meta positions to yield the trinitro compound.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 1,3,5-trinitrobenzene can be synthesized.

Interpretation Introduction

c)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2,4,6-tribromoaniline can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, the amino group is an ortho and para directing group. Nitration of benzene gives nitrobenzene. Nitrobenzene can be reduced to aminobenzene (aniline). Aniline upon bromoination will yield 2,4,6-tribromoaniline.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2,4,6-tribromoaniline can be synthesized.

Interpretation Introduction

d)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how m-fluorobenzoic acid can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions the carboxylic acid group is a meta directing group. Hence to prepare m- fluorobenzoic acid, benzene should be first converted into benzoicacid. Direct fluorination of aromatic rings is not possible as fluorine is too reactive and it is not possible to stop the reaction at the monofluorinated stage. Fluorination is normally carried out using F-TEDA-BF₄ which has a fluorine atom bonded to positively charged nitrogen.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how m-fluorobenzoic acid can be synthesized.

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Answer 5

Chapter 16.SE, Problem 57AP

Interpretation Introduction

a)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2-bromo-4-nitrotoluene can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens and methyl group are ortho and para directing groups while the nitro group is a meta directing group. Hence to prepare 2-bromo-4-nitrotoluene, toluene has to be halogenated and the chlorotoluene obtained should be nitrated.

Electrophilic substitution of di and trisubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2-bromo-4-nitrotoluene can be synthesized.

Interpretation Introduction

b)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 1,3,5-trinitrobenzene can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions the nitro group is a meta directing group. Nitration of benzene gives nitrobenzene. Further nitration of nitrobenzene will introduce nitro groups into the two meta positions to yield the trinitro compound.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 1,3,5-trinitrobenzene can be synthesized.

Interpretation Introduction

c)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2,4,6-tribromoaniline can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, the amino group is an ortho and para directing group. Nitration of benzene gives nitrobenzene. Nitrobenzene can be reduced to aminobenzene (aniline). Aniline upon bromoination will yield 2,4,6-tribromoaniline.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2,4,6-tribromoaniline can be synthesized.

Interpretation Introduction

d)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how m-fluorobenzoic acid can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions the carboxylic acid group is a meta directing group. Hence to prepare m- fluorobenzoic acid, benzene should be first converted into benzoicacid. Direct fluorination of aromatic rings is not possible as fluorine is too reactive and it is not possible to stop the reaction at the monofluorinated stage. Fluorination is normally carried out using F-TEDA-BF₄ which has a fluorine atom bonded to positively charged nitrogen.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how m-fluorobenzoic acid can be synthesized.

Answer 6

Chapter 16.SE, Problem 57AP

Interpretation Introduction

a)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2-bromo-4-nitrotoluene can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens and methyl group are ortho and para directing groups while the nitro group is a meta directing group. Hence to prepare 2-bromo-4-nitrotoluene, toluene has to be halogenated and the chlorotoluene obtained should be nitrated.

Electrophilic substitution of di and trisubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2-bromo-4-nitrotoluene can be synthesized.

Answer 7

Chapter 16.SE, Problem 57AP

Interpretation Introduction

a)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2-bromo-4-nitrotoluene can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens and methyl group are ortho and para directing groups while the nitro group is a meta directing group. Hence to prepare 2-bromo-4-nitrotoluene, toluene has to be halogenated and the chlorotoluene obtained should be nitrated.

Electrophilic substitution of di and trisubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2-bromo-4-nitrotoluene can be synthesized.

Answer 8

Interpretation Introduction

b)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 1,3,5-trinitrobenzene can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions the nitro group is a meta directing group. Nitration of benzene gives nitrobenzene. Further nitration of nitrobenzene will introduce nitro groups into the two meta positions to yield the trinitro compound.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 1,3,5-trinitrobenzene can be synthesized.

Answer 9

Interpretation Introduction

b)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 1,3,5-trinitrobenzene can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions the nitro group is a meta directing group. Nitration of benzene gives nitrobenzene. Further nitration of nitrobenzene will introduce nitro groups into the two meta positions to yield the trinitro compound.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 1,3,5-trinitrobenzene can be synthesized.

Answer 10

Interpretation Introduction

c)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2,4,6-tribromoaniline can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, the amino group is an ortho and para directing group. Nitration of benzene gives nitrobenzene. Nitrobenzene can be reduced to aminobenzene (aniline). Aniline upon bromoination will yield 2,4,6-tribromoaniline.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2,4,6-tribromoaniline can be synthesized.

Answer 11

Interpretation Introduction

c)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2,4,6-tribromoaniline can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, the amino group is an ortho and para directing group. Nitration of benzene gives nitrobenzene. Nitrobenzene can be reduced to aminobenzene (aniline). Aniline upon bromoination will yield 2,4,6-tribromoaniline.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2,4,6-tribromoaniline can be synthesized.

Answer 12

Interpretation Introduction

d)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how m-fluorobenzoic acid can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions the carboxylic acid group is a meta directing group. Hence to prepare m- fluorobenzoic acid, benzene should be first converted into benzoicacid. Direct fluorination of aromatic rings is not possible as fluorine is too reactive and it is not possible to stop the reaction at the monofluorinated stage. Fluorination is normally carried out using F-TEDA-BF₄ which has a fluorine atom bonded to positively charged nitrogen.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how m-fluorobenzoic acid can be synthesized.

Answer 13

Interpretation Introduction

d)

Interpretation:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how m-fluorobenzoic acid can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions the carboxylic acid group is a meta directing group. Hence to prepare m- fluorobenzoic acid, benzene should be first converted into benzoicacid. Direct fluorination of aromatic rings is not possible as fluorine is too reactive and it is not possible to stop the reaction at the monofluorinated stage. Fluorination is normally carried out using F-TEDA-BF₄ which has a fluorine atom bonded to positively charged nitrogen.

To state:

Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how m-fluorobenzoic acid can be synthesized.

Answer 14

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Answer 15

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Answer 25

Ch. 16.1 - Prob. 1P Ch. 16.2 - Propose a mechanism for the electrophilic...Ch. 16.2 - How many products might be formed on chlorination...Ch. 16.2 - When benzene is treated with D2SÅª4. deuterium...Ch. 16.3 - Prob. 5P Ch. 16.3 - What is the major monosubstitution product from...Ch. 16.3 - Identify the carboxylic acid chloride that might...Ch. 16.4 - Rank the compounds in each of the following groups...Ch. 16.4 - Predict the major products of the following...Ch. 16.4 - Prob. 10P

Solution Summary: The author explains how 2-bromo-4-nitrotoluene can be synthesized by nitrating benzine, methyl group, and nitro group.

Chapter 16 Solutions