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

An organic compound A of unknown structure was found to have a molecular formula C8H16. When A was poured in water and heated, compound B having a molecular formula C8H18O was formed. B upon heating with sulfuric acid was converted to C as the major product which is identical to A. Ozonolysis of C gave one molecule each of two different products D and E, both having a molecular formula C4H8O. Write the reactions involved and determine the structure of A,B,C,D and E.

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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An organic compound A of unknown structure was found to have a molecular formula C8H16. When A was poured in water and heated, compound B having a molecular formula C8H18O was formed. B upon heating with sulfuric acid was converted to C as the major product which is identical to A. Ozonolysis of C gave one molecule each of two different products D and E, both having a molecular formula C4H8O. Write the reactions involved and determine the structure of A,B,C,D and E.

Starting with the following compounds, outline a practical synthesis of 1-butanol

The sex attractant of the housefly has the formula C23H46. When treated with warm potassium permanganate, this pheromone gives two products: CH3(CH2)12COOH and CH3(CH2)7COOH. Suggest a structure for this sex attractant. Explainwhich part of the structure is uncertain

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.

Expert Solution & Answer

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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