Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
Question
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Chapter 16.10, Problem 22P
Interpretation Introduction

a) m-Chloronitrobenzene.

Interpretation:

How to synthesize m-chloronitrobenzene from benzene is to be shown.

Concept introduction:

In aromatic electrophilic substitution reactions the nitro group is meta directing. Since a meta chloronitrobenzene is to be synthesized, benzene is first nitrated and the nitrobenzene obtained is then chlorinated.

To show:

How to synthesize m-chloronitrobenzene from benzene.

Interpretation Introduction

b) m-Chloroethylbenzene.

Interpretation:

How to synthesize m-chloroethylbenzene from benzene is to be shown.

Concept introduction:

Since a meta halogen substituted alkyl benzene is to be synthesized benzene is first converted into a meta directing ketone by Friedal-Crafts acylation. The ketone upon halogenation will yield m-halogen substituted ketone which can be reduced to get the desired product.

To show:

How to synthesize m-chloroethylbenzene from benzene.

Interpretation Introduction

c) 4-Chloro-1-nitro-2-propylbenzene.

Interpretation:

How to synthesize 4-chloro-1-nitro-2-propylbenzene from benzene is to be shown.

Concept introduction:

Since a propyl benzene with a nitro group in the ortho position and a Cl at meta position is to be synthesized. Benzene is first converted into a meta directing ketone by Friedal-Crafts acylation. The ketone upon halogenation will yield a m-halogen substituted ketone which can be reduced to a m-chloroalkyl benzene. Alkyl groups are o- and p- directing. Hence by nitrating the m-chloroalkyl benzene the desired product can be synthesized.

To show:

How to synthesize 4-chloro-1-nitro-2-propylbenzene from benzene.

Interpretation Introduction

d) 3-Bromo-2-methylbenzenesulfonic acid.

Interpretation:

How to synthesize 3-bromo-2-methylbenzenesulfonic acid from benzene is to be shown.

Concept introduction:

A benzenesulfonic acid with a methyl group in the ortho position and a Br at the meta position is to be synthesized. Benzene is first converted into toluene by Friedal-Crafts alkylation. The toluene upon sulfonation will yield a methyl sulfonic acid. By brominating the methylsulfonic acid the desired product can be synthesized.

To show:

How to synthesize 3-bromo-2-methylbenzenesulfonic acid from benzene.

Blurred answer

Chapter 16 Solutions

Organic Chemistry

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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