Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 15.SE, Problem 20AP
Interpretation Introduction

a) Dinitrobenzene

Interpretation:

The possible isomers for dinitrobenzene are to be drawn and their names are to be given.

Concept introduction:

Disubstituted benzenes can exist as three isomers such as ortho, meta and para. They are named using the prefixes ortho (o), meta (m) and para (p). An ortho-disubstituted benzene has its two substituent groups in a 1,2-relationship on the ring. A meta-disubstituted benzene has its two substituent groups in a 1,3-relationship on the ring. A para-disubstituted benzene has its two substituent groups in a 1,4-relationship on the ring. While writing the name the substituent groups are arranged alphabetically.

To draw:

The possible isomers for dinitrobenzene and to name them.

Interpretation Introduction

b) Bromodimethylbenzene

Interpretation:

The possible isomers for bromodimethylbenzene are to be drawn and their names are to be given.

Concept introduction:

Trisubstitutedbenzenes can exist as six isomers with the three substituents in 1,2,3; 1,2,4; 1,2,5; 1,2,6; 1,3,4 and 1,3,5 relationship.

Benzene with more than two substituent groups are named choosing a point of attachment as carbon 1 and numbering the substituent groups on the ring so that the second substituent has as low number as possible. If ambiguity still exists, numbering is done such that the third and fourth substituent groups have a number as low as possible, until a point of difference is obtained. While writing the name the substituent groups are arranged alphabetically.

To draw:

The possible isomers for bromodimethylbenzene and to name them.

Interpretation Introduction

c) Trinitrophenol

Interpretation:

The possible isomers for trinitrophenol are to be drawn and their names are to be given.

Concept introduction:

Trinitrophenol can exist as six isomers with the four substituents in 1,2,3,4; 1,2,3,5; 1,2,3,6; 1,2,4,5; 1,2,4,6 and 1,3,4,5 relationship.

Benzene with more than two substituent groups are named choosing a point of attachment as carbon 1 and numbering the substituent groups on the ring so that the second substituent has as low number as possible. If ambiguity still exists, numbering is done such that the third and fourth substituent groups have a number as low as possible, until a point of difference is obtained. While writing the name the substituent groups are arranged alphabetically.

To draw:

The possible isomers for trinitrophenol and to name them.

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Chapter 15 Solutions

Organic Chemistry

Ch. 15.6 - Prob. 11PCh. 15.6 - How many electrons does each of the four nitrogen...Ch. 15.SE - Give IUPAC names for the following substances (red...Ch. 15.SE - All-cis cyclodecapentaene is a stable molecule...Ch. 15.SE - 1, 6-Methanonaphthalene has an interesting 1H NMR...Ch. 15.SE - Prob. 16VCCh. 15.SE - Azulene, an isomer of naphthalene, has a...Ch. 15.SE - Give IUPAC names for the following compounds:Ch. 15.SE - Draw structures corresponding to the following...Ch. 15.SE - Prob. 20APCh. 15.SE - Prob. 21APCh. 15.SE - Draw and name all possible aromatic compounds with...Ch. 15.SE - Propose structures for aromatic hydrocarbons that...Ch. 15.SE - Look at the three resonance structures of...Ch. 15.SE - Prob. 25APCh. 15.SE - Prob. 26APCh. 15.SE - Look at the five resonance structures for...Ch. 15.SE - Prob. 28APCh. 15.SE - 3-Chlorocyclopropene, on treatment with AgBF4,...Ch. 15.SE - Prob. 30APCh. 15.SE - Prob. 31APCh. 15.SE - Prob. 32APCh. 15.SE - Which would you expect to be most stable,...Ch. 15.SE - How might you convert 1, 3, 5, 7-cyclononatetraene...Ch. 15.SE - Calicene, like azulene (Problem 15-17), has an...Ch. 15.SE - Pentalene is a most elusive molecule that has been...Ch. 15.SE - Prob. 37APCh. 15.SE - Prob. 38APCh. 15.SE - Compound A, C8H10, yields three substitution...Ch. 15.SE - Prob. 40APCh. 15.SE - Propose structures for compounds that fit the...Ch. 15.SE - Prob. 42APCh. 15.SE - Prob. 43APCh. 15.SE - N-Phenylsydnone, so-named because it was first...Ch. 15.SE - Prob. 45APCh. 15.SE - Prob. 46APCh. 15.SE - Prob. 47APCh. 15.SE - Propose a structure for a molecule C14H12 that has...Ch. 15.SE - The proton NMR spectrum for a compound with...Ch. 15.SE - The proton NMR spectrum of a compound with formula...Ch. 15.SE - Aromatic substitution reactions occur by addition...Ch. 15.SE - Prob. 52APCh. 15.SE - Consider the aromatic anions below and their...Ch. 15.SE - After the reaction below, the chemical shift of Ha...Ch. 15.SE - Prob. 55APCh. 15.SE - Azo dyes are the major source of artificial color...
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