ORGANIC CHEMISTRY W/OWL
ORGANIC CHEMISTRY W/OWL
9th Edition
ISBN: 9781305717527
Author: McMurry
Publisher: CENGAGE C
Question
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Chapter 20.SE, Problem 17VC
Interpretation Introduction

a)

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 17VC , additional homework tip  1

Interpretation:

The IUPAC name of the compound represented by the model shown is to be given.

Concept introduction:

The names of simple carboxylic acids which are derivatives of open-chain alkanes are arrived by replacing the terminal –e of the corresponding alkane name by –oic acid. The numbering starts from carboxyl carbon. Compounds with –COOH bonded to a ring are named using the suffix-carboxylic acid. The –COOH carbon in this case is not numbered as C1, instead the carbon to which it is attached is numbered as C1. As a substituent, the –COOH group is called as carboxyl group.

To give:

The IUPAC name of the compound represented by the model shown.

Expert Solution
Check Mark

Answer to Problem 17VC

The IUPAC name is 3-bromo-4-methoxybenzoic acid.

Explanation of Solution

The compound represented by the model is

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 17VC , additional homework tip  2

It is a benzoic acid derivative with a bromine atom on C3 and a methoxyl group on C4.

Conclusion

The IUPAC name of the compound represented by the model shown is 3-bromo-4-methoxybenzoic acid.

Interpretation Introduction

b)

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 17VC , additional homework tip  3

Interpretation:

The IUPAC name of the compound represented by the model shown is to be given.

Concept introduction:

The names of simple carboxylic acids which are derivatives of open-chain alkanes are arrived by replacing the terminal –e of the corresponding alkane name by –oic acid. The numbering starts from carboxyl carbon. Compounds with –COOH bonded to a ring are named using the suffix-carboxylic acid. The –COOH carbon in this case is not numbered as C1, instead the carbon to which it is attached is numbered as C1. As a substituent, the –COOH group is called as carboxyl group.

To give:

The IUPAC name of the compound represented by the model shown.

Expert Solution
Check Mark

Answer to Problem 17VC

The IUPAC name of the compound represented by the model shown is 3-methyl-2-butenoic acid.

Explanation of Solution

The compound represented by the model is

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 17VC , additional homework tip  4

The compound is an unsaturated acid having a four carbon straight chain with a double bond between C2 and C3.

Conclusion

The IUPAC name of the compound represented by the model shown is 3-methyl-2-butenoic acid.

Interpretation Introduction

c)

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 17VC , additional homework tip  5

Interpretation:

The IUPAC name of the compound represented by the model shown is to be given.

Concept introduction:

The names of simple carboxylic acids which are derivatives of open-chain alkanes are arrived by replacing the terminal –e of the corresponding alkane name by –oic acid. The numbering starts from carboxyl carbon. Compounds with –COOH bonded to a ring are named using the suffix-carboxylic acid. The –COOH carbon in this case is not numbered as C1, instead the carbon to which it is attached is numbered as C1. As a substituent, the –COOH group is called as carboxyl group.

To give:

The IUPAC name of the compound represented by the model shown.

Expert Solution
Check Mark

Answer to Problem 17VC

The IUPAC name of the compound represented by the model shown is cyclopenta-1,3-dienecarboxylic acid.

Explanation of Solution

The compound represented by the model is

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 17VC , additional homework tip  6

The compound has a cyclopentadiene ring to which a carboxyl group is attached. The double bonds in the diene are in between C1 & C2 and C3 & C4.

Conclusion

The IUPAC name of the compound represented by the model shown is cyclopenta-1,3-dienecarboxylic acid.

Interpretation Introduction

d)

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 17VC , additional homework tip  7

Interpretation:

The IUPAC name of the compound represented by the model shown is to be given.

Concept introduction:

The names of simple carboxylic acids which are derivatives of open-chain alkanes are arrived by replacing the terminal –e of the corresponding alkane name by –oic acid. The numbering starts from carboxyl carbon. Compounds with –COOH bonded to a ring are named using the suffix-carboxylic acid. The –COOH carbon in this case is not numbered as C1, instead the carbon to which it is attached is numbered as C1. As a substituent, the –COOH group is called as carboxyl group.

To give:

The IUPAC name of the compound represented by the model shown.

Expert Solution
Check Mark

Answer to Problem 17VC

The IUPAC name of the compound represented by the model shown is (S)-3-cyclopentyl-2-methylpropanoic acid.

Explanation of Solution

The compound represented by the model is

ORGANIC CHEMISTRY W/OWL, Chapter 20.SE, Problem 17VC , additional homework tip  8

The compound is a carboxylic acid with a three carbon straight chin and has a methyl group attached to C2 and cyclopentyl group attached to C3. The compound is optically active as C2 is chiral. The groups of first highest, second highest and third highest groups when viewed away from the group of last priority are arranged in the anti-clockwise direction. Hence the compound has S stereochemistry.

Conclusion

The IUPAC name of the compound represented by the model shown is (S)-3-cyclopentyl-2-methylpropanoic acid.

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Chapter 20 Solutions

ORGANIC CHEMISTRY W/OWL

Ch. 20.6 - Prob. 11PCh. 20.6 - How might you carry out the following...Ch. 20.7 - Prob. 13PCh. 20.7 - Prob. 14PCh. 20.8 - Cyclopentanecarboxylic acid and...Ch. 20.8 - Prob. 16PCh. 20.SE - Prob. 17VCCh. 20.SE - Prob. 18VCCh. 20.SE - The following carboxylic acid can’t be prepared...Ch. 20.SE - Electrostatic potential maps of anisole and...Ch. 20.SE - Predict the product(s) and provide the mechanism...Ch. 20.SE - Predict the product(s) and provide the mechanism...Ch. 20.SE - Prob. 23MPCh. 20.SE - Predict the product(s) and provide the complete...Ch. 20.SE - Acid-catalyzed hydrolysis of a nitrile to give a...Ch. 20.SE - Prob. 26MPCh. 20.SE - Naturally occurring compounds called cyanogenic...Ch. 20.SE - 2-Bromo-6, 6-dimethylcyclohexanone gives 2,...Ch. 20.SE - Naturally occurring compounds called terpenoids,...Ch. 20.SE - In the Ritter reaction, an alkene reacts with a...Ch. 20.SE - Give IUPAC names for the following compounds:Ch. 20.SE - Prob. 32APCh. 20.SE - Prob. 33APCh. 20.SE - Prob. 34APCh. 20.SE - Prob. 35APCh. 20.SE - Prob. 36APCh. 20.SE - Prob. 37APCh. 20.SE - Prob. 38APCh. 20.SE - Calculate the Ka's for the following acids: (a)...Ch. 20.SE - Thioglycolic acid, HSCH2CO2H, a substance used in...Ch. 20.SE - Prob. 41APCh. 20.SE - Prob. 42APCh. 20.SE - How could you convert butanoic acid into the...Ch. 20.SE - How could you convert each of the following...Ch. 20.SE - How could you convert butanenitrile into the...Ch. 20.SE - How would you prepare the following compounds from...Ch. 20.SE - Prob. 47APCh. 20.SE - Using 13CO2 as your only source of labeled carbon,...Ch. 20.SE - Prob. 49APCh. 20.SE - Which method-Grignard carboxylation or nitrile...Ch. 20.SE - Prob. 51APCh. 20.SE - Prob. 52APCh. 20.SE - Propose a structure for a compound C6H12O2 that...Ch. 20.SE - Prob. 54APCh. 20.SE - How would you use NMR (either 13C or 1H) to...Ch. 20.SE - Prob. 56APCh. 20.SE - A chemist in need of 2,2-dimethylpentanoic acid...Ch. 20.SE - Prob. 58APCh. 20.SE - Prob. 59APCh. 20.SE - Prob. 60APCh. 20.SE - Prob. 61APCh. 20.SE - Prob. 62APCh. 20.SE - Prob. 63APCh. 20.SE - The following pKa values have been measured....Ch. 20.SE - Identify the missing reagents a-f in the following...Ch. 20.SE - Propose a structure for a compound, C4H7N, that...Ch. 20.SE - Prob. 67APCh. 20.SE - The 1H and 13C NMR spectra below belong to a...Ch. 20.SE - Propose structures for carboxylic acids that show...Ch. 20.SE - Carboxylic acids having a second carbonyl group...
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