ORGANIC CHEMISTRY-EBOOK>I<
ORGANIC CHEMISTRY-EBOOK>I<
9th Edition
ISBN: 9781305084414
Author: McMurry
Publisher: INTER CENG
Question
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Chapter 16.SE, Problem 57AP
Interpretation Introduction

a)

ORGANIC CHEMISTRY-EBOOK>I<, Chapter 16.SE, Problem 57AP , additional homework tip  1

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)

ORGANIC CHEMISTRY-EBOOK>I<, Chapter 16.SE, Problem 57AP , additional homework tip  2

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)

ORGANIC CHEMISTRY-EBOOK>I<, Chapter 16.SE, Problem 57AP , additional homework tip  3

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)

ORGANIC CHEMISTRY-EBOOK>I<, Chapter 16.SE, Problem 57AP , additional homework tip  4

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 this question please solve the first question. Please explain your thought process, the steps you took, and how you would tackle a similar problem. Thank you for your help!

Chapter 16 Solutions

ORGANIC CHEMISTRY-EBOOK>I<

Ch. 16.4 - Prob. 11PCh. 16.4 - Acetanilide is less reactive than aniline toward...Ch. 16.4 - Prob. 13PCh. 16.5 - At what position would you expect electrophilic...Ch. 16.5 - Show the major product(s) from reaction of the...Ch. 16.6 - The herbicide oxyfluorfen can be prepared by...Ch. 16.7 - Treatment of p-bromotoluene with NaOH at 300°C...Ch. 16.8 - Prob. 18PCh. 16.8 - Prob. 19PCh. 16.8 - Prob. 20PCh. 16.9 - Prob. 21PCh. 16.10 - Prob. 22PCh. 16.10 - Prob. 23PCh. 16.SE - Prob. 24VCCh. 16.SE - The following molecular model of a...Ch. 16.SE - Prob. 26VCCh. 16.SE - Prob. 27VCCh. 16.SE - Aromatic iodination can be carried out with a...Ch. 16.SE - Prob. 29MPCh. 16.SE - The carbocation electrophile in a Friede1-Crafts...Ch. 16.SE - Prob. 31MPCh. 16.SE - The nitroso group, —N=O, is one of the few...Ch. 16.SE - Triphenylmethane can be prepared by reaction of...Ch. 16.SE - Using resonance structures of the intermediates,...Ch. 16.SE - Benzene and alkyl -substituted benzenes can be...Ch. 16.SE - Prob. 36MPCh. 16.SE - Hexachlorophene, a substance used in the...Ch. 16.SE - Benzenediazonium carboxylate decomposes when...Ch. 16.SE - 4-Chloropyridine undergoes reaction with...Ch. 16.SE - Propose a mechanism to account for the following...Ch. 16.SE - In the Gatterman-Kochreaction, a formyl group...Ch. 16.SE - Treatment of p-tert-butylphenol with a strong acid...Ch. 16.SE - Benzyl bromide is converted into benzaldehyde by...Ch. 16.SE - Prob. 44MPCh. 16.SE - Prob. 45MPCh. 16.SE - Prob. 46APCh. 16.SE - Prob. 47APCh. 16.SE - Prob. 48APCh. 16.SE - Predict the major monoalkylation products you...Ch. 16.SE - Name and draw the major product(s) of...Ch. 16.SE - Prob. 51APCh. 16.SE - Prob. 52APCh. 16.SE - What product(s) would you expect to obtain from...Ch. 16.SE - Prob. 54APCh. 16.SE - How would you synthesize the following substances...Ch. 16.SE - Prob. 56APCh. 16.SE - Prob. 57APCh. 16.SE - Prob. 58APCh. 16.SE - Prob. 59APCh. 16.SE - Prob. 60APCh. 16.SE - Prob. 61APCh. 16.SE - Prob. 62APCh. 16.SE - Prob. 63APCh. 16.SE - How would you synthesize the following substances...Ch. 16.SE - Prob. 65APCh. 16.SE - Prob. 66APCh. 16.SE - Draw resonance structures of the intermediate...Ch. 16.SE - Prob. 68APCh. 16.SE - p-Bromotoluene reacts with potassium amide to give...Ch. 16.SE - Prob. 70APCh. 16.SE - Prob. 71APCh. 16.SE - Prob. 72APCh. 16.SE - Use your knowledge of directing effects, along...Ch. 16.SE - Identify the reagents represented by the letters...Ch. 16.SE - Phenols (ArOH) are relatively acidic, and the...Ch. 16.SE - Prob. 76APCh. 16.SE - Prob. 77APCh. 16.SE - Melamine, used as a fire retardant and a component...
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