Package: Organic Chemistry with Connect 2-year Access Card
Package: Organic Chemistry with Connect 2-year Access Card
5th Edition
ISBN: 9781259729959
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 19, Problem 19.30P

Draw the structure corresponding to each name.

(a) 3 , 3 dimethylpentanoic acid

(b) 4 chloro 3 phenylheptanoic acid

(c) ( R ) 2 chloropropanoic acid

(d) m hydroxybenzoic acid

(e) potassium acetate

(f) sodium α bromobutyrate

(g) 2 , 2 dichloropentanedioic acid

(h) 4 isopropyl 2 methyloctanedioic acid

Expert Solution
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Interpretation Introduction

(a)

Interpretation: The structure corresponding to the given name is to be stated.

Concept introduction: International Union of Pure and Applied Chemistry gave guidelines to write the chemical name of molecules. There are three steps to derive the structure of the compound from its IUPAC name. The first step involves the identification of the parent name and the functional group found at the end of the name. The second step is numbering of carbon skeleton in either direction. The third step is the addition of substituents at appropriate carbon atoms.

Answer to Problem 19.30P

The structure corresponding to 3,3dimethylpentanoic acid is,

Package: Organic Chemistry with Connect 2-year Access Card, Chapter 19, Problem 19.30P , additional homework tip  1

Explanation of Solution

The name of the compound is 3,3dimethylpentanoic acid. The name suggests that the longest carbon chain consists of five carbon atoms. On third carbon atom, two methyl groups are attached. Therefore, the structure corresponding to the given name is,

Package: Organic Chemistry with Connect 2-year Access Card, Chapter 19, Problem 19.30P , additional homework tip  2

Figure 1

Conclusion

The structure of 3,3dimethylpentanoic acid is drawn in Figure 1.

Expert Solution
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Interpretation Introduction

(b)

Interpretation: The structure corresponding to the given name is to be stated.

Concept introduction: International Union of Pure and Applied Chemistry gave guidelines to write the chemical name of molecules. There are three steps to derive the structure of the compound from its IUPAC name. The first step involves the identification of the parent name and the functional group found at the end of the name. The second step is numbering of carbon skeleton in either direction. The third step is the addition of substituents at appropriate carbon atoms.

Answer to Problem 19.30P

The structure corresponding to 4chloro3phenylheptanoic acid is,

Package: Organic Chemistry with Connect 2-year Access Card, Chapter 19, Problem 19.30P , additional homework tip  3

Explanation of Solution

The name of the compound is 4chloro3phenylheptanoic acid. The name suggests that the longest carbon chain consists of seven carbon atoms. On third and fourth carbon atoms, phenyl and chlorine groups are attached respectively. Therefore, the structure corresponding to the given name is,

Package: Organic Chemistry with Connect 2-year Access Card, Chapter 19, Problem 19.30P , additional homework tip  4

Figure 2

Conclusion

The structure of 4chloro3phenylheptanoic acid is drawn in Figure 2.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The structure corresponding to the given name is to be stated.

Concept introduction: International Union of Pure and Applied Chemistry gave guidelines to write the chemical name of molecules. There are three steps to derive the structure of the compound from its IUPAC name. The first step involves the identification of the parent name and the functional group found at the end of the name. The second step is numbering of carbon skeleton in either direction. The third step is the addition of substituents at appropriate carbon atoms.

Answer to Problem 19.30P

The structure corresponding to (R)2chloropropanoic acid is,

Package: Organic Chemistry with Connect 2-year Access Card, Chapter 19, Problem 19.30P , additional homework tip  5

Explanation of Solution

The name of the compound is (R)2chloropropanoic acid. The name suggests that the longest carbon chain consists of three carbon atoms. Chlorine group is attached to the second carbon atom.

The stereochemistry of the compound is determined by prioritizing the groups attached to its stereogenic center. The groups are prioritized on the basis of atomic number of their atoms. The configuration of the compound is R because the movement from higher priority to lower priority substituent is in anti clockwise direction and the lowest priority group is present above the plane.

Therefore, the structure corresponding to the given name is,

Package: Organic Chemistry with Connect 2-year Access Card, Chapter 19, Problem 19.30P , additional homework tip  6

Figure 3

Conclusion

The structure of (R)2chloropropanoic acid is drawn in Figure 3.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The structure corresponding to given name is to be stated.

Concept introduction: International Union of Pure and Applied Chemistry gave guidelines to write the chemical name of molecules. There are three steps to derive the structure of the compound from its IUPAC name. The first step involves the identification of the parent name and the functional group found at the end of the name. The second step is numbering of carbon skeleton in either direction. The third step is the addition of substituents at appropriate carbon atoms.

Answer to Problem 19.30P

The structure corresponding to mhydroxybenzoic acid is,

Package: Organic Chemistry with Connect 2-year Access Card, Chapter 19, Problem 19.30P , additional homework tip  7

Explanation of Solution

The name of the compound is mhydroxybenzoic acid. The name suggests that the compound contains an aromatic benzene ring. The functional group present in the compound is carboxylic acid. The hydroxyl group is attached at meta position in the benzoic acid. Therefore, the structure corresponding to the given name is,

Package: Organic Chemistry with Connect 2-year Access Card, Chapter 19, Problem 19.30P , additional homework tip  8

Figure 4

Conclusion

The structure of mhydroxybenzoic acid is drawn in Figure 4.

Expert Solution
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Interpretation Introduction

(e)

Interpretation: The structure corresponding to the given name is to be stated.

Concept introduction: International Union of Pure and Applied Chemistry gave guidelines to write the chemical name of molecules. There are three steps to derive the structure of the compound from its IUPAC name. The first step involves the identification of the parent name and the functional group found at the end of the name. The second step is numbering of carbon skeleton in either direction. The third step is the addition of substituents at appropriate carbon atoms.

Answer to Problem 19.30P

The structure corresponding to potassium acetate is,

Package: Organic Chemistry with Connect 2-year Access Card, Chapter 19, Problem 19.30P , additional homework tip  9

Explanation of Solution

The name of the compound is potassium acetate. The name suggests that potassium is present in the place of hydrogen in acetic acid. Therefore, the structure corresponding to the given name is,

Package: Organic Chemistry with Connect 2-year Access Card, Chapter 19, Problem 19.30P , additional homework tip  10

Figure 5

Conclusion

The structure of potassium acetate is drawn in Figure 5.

Expert Solution
Check Mark
Interpretation Introduction

(f)

Interpretation: The structure corresponding to the given name is to be stated.

Concept introduction: International Union of Pure and Applied Chemistry gave guidelines to write the chemical name of molecules. There are three steps to derive the structure of the compound from its IUPAC name. The first step involves the identification of the parent name and the functional group found at the end of the name. The second step is numbering of carbon skeleton in either direction. The third step is the addition of substituents at appropriate carbon atoms.

Answer to Problem 19.30P

The structure corresponding to sodium αbromobutyrate is,

Package: Organic Chemistry with Connect 2-year Access Card, Chapter 19, Problem 19.30P , additional homework tip  11

Explanation of Solution

The name of the compound is sodium αbromobutyrate. The name suggests that the longest carbon chain consists of four carbon atoms. On second carbon atom, bromine group is attached. Therefore, the structure corresponding to the given name is,

Package: Organic Chemistry with Connect 2-year Access Card, Chapter 19, Problem 19.30P , additional homework tip  12

Figure 6

Conclusion

The structure of sodium αbromobutyrate is drawn in Figure 6.

Expert Solution
Check Mark
Interpretation Introduction

(g)

Interpretation: The structure corresponding to the given name is to be stated.

Concept introduction: International Union of Pure and Applied Chemistry gave guidelines to write the chemical name of molecules. There are three steps to derive the structure of the compound from its IUPAC name. The first step involves the identification of the parent name and the functional group found at the end of the name. The second step is numbering of carbon skeleton in either direction. The third step is the addition of substituents at appropriate carbon atoms.

Answer to Problem 19.30P

The structure corresponding to 2,2dichloropentanedioic acid is,

Package: Organic Chemistry with Connect 2-year Access Card, Chapter 19, Problem 19.30P , additional homework tip  13

Explanation of Solution

The name of the compound is 2,2dichloropentanedioic acid. The name suggests that the longest carbon chain consists of five carbon atoms. On second carbon atom, two chlorine groups are attached. Therefore, the structure corresponding to the given name is,

Package: Organic Chemistry with Connect 2-year Access Card, Chapter 19, Problem 19.30P , additional homework tip  14

Figure 7

Conclusion

The structure of 2,2dichloropentanedioic acid is drawn in Figure 7.

Expert Solution
Check Mark
Interpretation Introduction

(h)

Interpretation: The structure corresponding to the given name is to be stated.

Concept introduction: International Union of Pure and Applied Chemistry gave guidelines to write the chemical name of molecules. There are three steps to derive the structure of the compound from its IUPAC name. The first step involves the identification of the parent name and the functional group found at the end of the name. The second step is numbering of carbon skeleton in either direction. The third step is the addition of substituents at appropriate carbon atoms.

Answer to Problem 19.30P

The structure corresponding to 4isopropyl2methyloctanedioic acid is,

Package: Organic Chemistry with Connect 2-year Access Card, Chapter 19, Problem 19.30P , additional homework tip  15

Explanation of Solution

The name of the compound is 4isopropyl2methyloctanedioic acid. The name suggests that the longest carbon chain consists of eight carbon atoms. On second and fourth carbon atom, methyl and isopropyl groups are attached. Therefore, the structure corresponding to the given name is,

Package: Organic Chemistry with Connect 2-year Access Card, Chapter 19, Problem 19.30P , additional homework tip  16

Figure 8

Conclusion

The structure of 4isopropyl2methyloctanedioic acid 2,2dichloropentanedioic acid is drawn in Figure 8.

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Chapter 19 Solutions

Package: Organic Chemistry with Connect 2-year Access Card

Ch. 19 - Problem 19.11 Identify A-D in the following...Ch. 19 - Problem 9.12 Draw the cation that results when a...Ch. 19 - Problem 19.13 Draw the products of each acid-base...Ch. 19 - Problem 19.14 Given the values in Appendix A,...Ch. 19 - Problem 19.15 Rank the labeled protons in...Ch. 19 - Problem 19.16 Match each of the following values ...Ch. 19 - Problem 19.17 Rank the compounds in each group in...Ch. 19 - Problem 19.18 Rank the compounds in each group in...Ch. 19 - Prob. 19.19PCh. 19 - Problem 19.20 Which of the following pairs of...Ch. 19 - Problem 19.21 Two other commonly used sulfonic...Ch. 19 - Problem 19.22 Draw both enantiomers of each amino...Ch. 19 - Problem 19.23 Explain why amino acids, unlike most...Ch. 19 - Problem 19.24 Draw the positively charged,...Ch. 19 - Prob. 19.25PCh. 19 - Problem 19.26 Explain why the of the group of...Ch. 19 - Answer each question for A and B depicted in the...Ch. 19 - Prob. 19.28PCh. 19 - 19.29 Give the IUPAC name for each compound. a....Ch. 19 - 19.30 Draw the structure corresponding to each...Ch. 19 - Prob. 19.31PCh. 19 - 19.32 Rank the following compounds in order of...Ch. 19 - 19.33 Draw the organic products formed in each...Ch. 19 - 19.34 Identify the lettered compounds in each...Ch. 19 - 19.35 Using the table in Appendix A, determine...Ch. 19 - 19.36 Draw the products of each acid-base...Ch. 19 - 19.37 Which compound in each pair has the lower ?...Ch. 19 - 19.38 Rank the compounds in each group in order of...Ch. 19 - 19.39 Rank the compounds in each group in order of...Ch. 19 - 19.40 Match the values to the appropriate...Ch. 19 - Prob. 19.41PCh. 19 - 19.42 Which carboxylic acid has the lower ,...Ch. 19 - Prob. 19.43PCh. 19 - 19.44 Explain the following statement. Although...Ch. 19 - Prob. 19.45PCh. 19 - 19.46 Explain why the of compound A is lower than...Ch. 19 - 19.47 Rank the following compounds in order of...Ch. 19 - Prob. 19.48PCh. 19 - Prob. 19.49PCh. 19 - 19.50 Draw all resonance structures of the...Ch. 19 - As we will see in Chapter 23, CH bonds are...Ch. 19 - Prob. 19.52PCh. 19 - The pKa of acetamide (CH3CONH2) is 16. Draw the...Ch. 19 - 19.54 Write out the steps needed to separate...Ch. 19 - Prob. 19.55PCh. 19 - Can octane and octan -1- ol be separated using an...Ch. 19 - 19.57 Identify each compound from its spectral...Ch. 19 - 19.58 Use the NMR and IR spectra given below to...Ch. 19 - 19.59 An unknown compound (molecular formula )...Ch. 19 - 19.60 Propose a structure for (molecular formula...Ch. 19 - 19.61 Match the data to the appropriate...Ch. 19 - Prob. 19.62PCh. 19 - Prob. 19.63PCh. 19 - Prob. 19.64PCh. 19 - 19.65 For each amino acid ,draw its neutral,...Ch. 19 - Calculate the isoelectric point for each amino...Ch. 19 - 19.67 Lysine and tryptophan are two amino acids...Ch. 19 - Prob. 19.68PCh. 19 - Prob. 19.69PCh. 19 - Prob. 19.70PCh. 19 - 19.71 Hydroxy butanedioic acid occurs naturally in...Ch. 19 - 19.72 Although it was initially sold as a rat...
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