Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
Question
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Chapter 17, Problem 17.10P

(a)

Interpretation Introduction

Interpretation: The structural formula for the given compound has to be drawn.

Concept introduction:

Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,

Organic Chemistry, Chapter 17, Problem 17.10P , additional homework tip  1

Nomenclature of carboxylic acid:

  • • Find the Parent hydrocarbon chain.
  • • Carboxyl carbon must be numbered first.
  • • Replace the –e in the alkane name with –oic acid.

Naming of compounds with two functional groups;

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  ClassSuffix namePrefix nameCarboxylic acid-oic acidCarboxyEster-oateAlkoxy carbonylAmide-amideAmidoNitrile-ntrileCyanoAldehyde-alOxo(=O)Aldehyde-alFormyl(-CH=O)Ketone-oneOxo(=O)Alcohol-olHydroxyAmine-amineAminoAlkene-eneAlkenylAlkyne-yneAlkynylAlkane-aneAlkylEther---AlkoxyAlkylhalide---Halo

Carboxylic salts are the water-soluble ammonium or alkali metal salts of carboxylic acids.

(a)

Expert Solution
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Explanation of Solution

Name of the given salt is sodium benzoate.

From the name, we will get the following fact about the structure of the compound.

  • ✓ The given compound is a sodium salt of benzoic acid.

Thus,

The structural formula for this salt can be drawn as shown below,

Organic Chemistry, Chapter 17, Problem 17.10P , additional homework tip  2

(b)

Interpretation Introduction

Interpretation: The structural formula for the given compound has to be drawn.

Concept introduction:

Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,

Organic Chemistry, Chapter 17, Problem 17.10P , additional homework tip  3

Nomenclature of carboxylic acid:

  • • Find the Parent hydrocarbon chain.
  • • Carboxyl carbon must be numbered first.
  • • Replace the –e in the alkane name with –oic acid. If two or more carboxylic functional groups are present in the same compound then its number should be taken in to consideration and the prefix di, tri, tetra.. must be used.

Naming of compounds with two functional groups;

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  ClassSuffix namePrefix nameCarboxylic acid-oic acidCarboxyEster-oateAlkoxy carbonylAmide-amideAmidoNitrile-ntrileCyanoAldehyde-alOxo(=O)Aldehyde-alFormyl(-CH=O)Ketone-oneOxo(=O)Alcohol-olHydroxyAmine-amineAminoAlkene-eneAlkenylAlkyne-yneAlkynylAlkane-aneAlkylEther---AlkoxyAlkylhalide---Halo

Carboxylic salts are the water-soluble ammonium or alkali metal salts of carboxylic acids.

(b)

Expert Solution
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Explanation of Solution

Name of the given salt is Lithium acetate.

From the name, we will get the following fact about the structure of the compound.

  • ✓ The given compound is a Lithium salt of acetic acid

Thus,

The structural formula for this compound can be drawn as shown below,

Organic Chemistry, Chapter 17, Problem 17.10P , additional homework tip  4

(c)

Interpretation Introduction

Interpretation: The structural formula for the given compound has to be drawn.

Concept introduction:

Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,

Organic Chemistry, Chapter 17, Problem 17.10P , additional homework tip  5

Nomenclature of carboxylic acid:

  • • Find the Parent hydrocarbon chain.
  • • Carboxyl carbon must be numbered first.
  • • Replace the –e in the alkane name with –oic acid.

Naming of compounds with two functional groups;

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  ClassSuffix namePrefix nameCarboxylic acid-oic acidCarboxyEster-oateAlkoxy carbonylAmide-amideAmidoNitrile-ntrileCyanoAldehyde-alOxo(=O)Aldehyde-alFormyl(-CH=O)Ketone-oneOxo(=O)Alcohol-olHydroxyAmine-amineAminoAlkene-eneAlkenylAlkyne-yneAlkynylAlkane-aneAlkylEther---AlkoxyAlkylhalide---Halo

Carboxylic salts are the water-soluble ammonium or alkali metal salts of carboxylic acids.

(c)

Expert Solution
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Explanation of Solution

Name of the given salt is Ammonium acetate.

From the name, we will get the following fact about the structure of the compound.

  • ✓ The given compound is an ammonium salt of acetic acid.

Thus,

The structural formula for this compound can be drawn as shown below,

Organic Chemistry, Chapter 17, Problem 17.10P , additional homework tip  6

(d)

Interpretation Introduction

Interpretation: The structural formula for the given compound has to be drawn.

Concept introduction:

Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,

Organic Chemistry, Chapter 17, Problem 17.10P , additional homework tip  7

Nomenclature of carboxylic acid:

  • • Find the Parent hydrocarbon chain.
  • • Carboxyl carbon must be numbered first.
  • • Replace the –e in the alkane name with –oic acid.

Naming of compounds with two functional groups;

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  ClassSuffix namePrefix nameCarboxylic acid-oic acidCarboxyEster-oateAlkoxy carbonylAmide-amideAmidoNitrile-ntrileCyanoAldehyde-alOxo(=O)Aldehyde-alFormyl(-CH=O)Ketone-oneOxo(=O)Alcohol-olHydroxyAmine-amineAminoAlkene-eneAlkenylAlkyne-yneAlkynylAlkane-aneAlkylEther---AlkoxyAlkylhalide---Halo

Carboxylic salts are the water-soluble ammonium or alkali metal salts of carboxylic acids.

(d)

Expert Solution
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Explanation of Solution

Name of the given salt is Disodium adipate.

From the name, we will get the following facts about the structure of the compound.

  • ✓ The given compound is a sodium salt of adipic acid.
  • ✓ Two sodium atoms are attached to the both carboxyl group of adipic acid.

The structure of adipic acid is shown below,

Organic Chemistry, Chapter 17, Problem 17.10P , additional homework tip  8

Thus,

The structural formula for this compound can be drawn as shown below,

Organic Chemistry, Chapter 17, Problem 17.10P , additional homework tip  9

(e)

Interpretation Introduction

Interpretation: The structural formula for the given compound has to be drawn.

Concept introduction:

Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,

Organic Chemistry, Chapter 17, Problem 17.10P , additional homework tip  10

Nomenclature of carboxylic acid:

  • • Find the Parent hydrocarbon chain.
  • • Carboxyl carbon must be numbered first.
  • • Replace the –e in the alkane name with –oic acid.

Naming of compounds with two functional groups;

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  ClassSuffix namePrefix nameCarboxylic acid-oic acidCarboxyEster-oateAlkoxy carbonylAmide-amideAmidoNitrile-ntrileCyanoAldehyde-alOxo(=O)Aldehyde-alFormyl(-CH=O)Ketone-oneOxo(=O)Alcohol-olHydroxyAmine-amineAminoAlkene-eneAlkenylAlkyne-yneAlkynylAlkane-aneAlkylEther---AlkoxyAlkylhalide---Halo

Carboxylic salts are the water-soluble ammonium or alkali metal salts of carboxylic acids.

(e)

Expert Solution
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Explanation of Solution

Name of the given salt is sodium salicylate.

From the name, we will get the following fact about the structure of the compound.

  • ✓ The compound is a sodium salt of salicylic acid.

Structure of salicylic acid is shown below,

Organic Chemistry, Chapter 17, Problem 17.10P , additional homework tip  11

Thus,

The structural formula for this compound can be drawn as shown below,

Organic Chemistry, Chapter 17, Problem 17.10P , additional homework tip  12

(f)

Interpretation Introduction

Interpretation: The structural formula for the given compound has to be drawn.

Concept introduction:

Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,

Organic Chemistry, Chapter 17, Problem 17.10P , additional homework tip  13

Nomenclature of carboxylic acid:

  • • Find the Parent hydrocarbon chain.
  • • Carboxyl carbon must be numbered first.
  • • Replace the –e in the alkane name with –oic acid. If two or more carboxylic functional groups are present in the same compound then its number should be taken in to consideration and the prefix di, tri, tetra.. must be used.

Naming of compounds with two functional groups;

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  ClassSuffix namePrefix nameCarboxylic acid-oic acidCarboxyEster-oateAlkoxy carbonylAmide-amideAmidoNitrile-ntrileCyanoAldehyde-alOxo(=O)Aldehyde-alFormyl(-CH=O)Ketone-oneOxo(=O)Alcohol-olHydroxyAmine-amineAminoAlkene-eneAlkenylAlkyne-yneAlkynylAlkane-aneAlkylEther---AlkoxyAlkylhalide---Halo

Carboxylic salts are the water-soluble ammonium or alkali metal salts of carboxylic acids.

(f)

Expert Solution
Check Mark

Explanation of Solution

Name of the given salt is calcium butanoate.

From the name, we will get the following fact about the structure of the compound.

  • ✓ The given compound is a calcium salt of butanoic acid.

Thus,

The structural formula for this compound can be drawn as shown below,

Organic Chemistry, Chapter 17, Problem 17.10P , additional homework tip  14

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Chapter 17 Solutions

Organic Chemistry

Ch. 17 - Write the IUPAC name of each compound, showing...Ch. 17 - Prob. 17.8PCh. 17 - Prob. 17.9PCh. 17 - Prob. 17.10PCh. 17 - Prob. 17.11PCh. 17 - Prob. 17.12PCh. 17 - Prob. 17.13PCh. 17 - On a cyclohexane ring, an axial carboxyl group has...Ch. 17 - Prob. 17.15PCh. 17 - Prob. 17.16PCh. 17 - Prob. 17.17PCh. 17 - Complete each reaction.Ch. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Show the reagents and experimental conditions...Ch. 17 - Prob. 17.23PCh. 17 - Prob. 17.24PCh. 17 - Prob. 17.25PCh. 17 - In each set, assign the acid its appropriate pKa.Ch. 17 - Low-molecular-weight dicarboxylic acids normally...Ch. 17 - Complete the following acid-base reactions. (a)...Ch. 17 - Prob. 17.29PCh. 17 - Prob. 17.30PCh. 17 - Excess ascorbic acid is excreted in the urine, the...Ch. 17 - Give the expected organic product when...Ch. 17 - Show how to convert trans-3-phenyl-2-propenoic...Ch. 17 - Show how to convert 3-oxobutanoic acid...Ch. 17 - Prob. 17.35PCh. 17 - Prob. 17.36PCh. 17 - Prob. 17.37PCh. 17 - When 4-hydroxybutanoic acid is treated with an...Ch. 17 - Fischer esterification cannot be used to prepare...Ch. 17 - Draw the product formed on thermal decarboxylation...Ch. 17 - Prob. 17.41PCh. 17 - Show how cyclohexanecarboxylic acid could be...Ch. 17 - Prob. 17.43PCh. 17 - Prob. 17.44PCh. 17 - Prob. 17.45PCh. 17 - Write the products of the following sequences of...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Prob. 17.51PCh. 17 - Complete the following Fischer esterification...Ch. 17 - Prob. 17.53P
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