Organic Chemistry-Package(Custom)
Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 19, Problem 19.29P
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.

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Answer to Problem 19.29P

The structure corresponding to 3,3 dimethylpentanoic acid is,

Organic Chemistry-Package(Custom), Chapter 19, Problem 19.29P , additional homework tip  1

Explanation of Solution

The name of the compound is 3,3 dimethylpentanoic 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,

Organic Chemistry-Package(Custom), Chapter 19, Problem 19.29P , additional homework tip  2

Figure 1

Conclusion

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

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 theparent 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.

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Answer to Problem 19.29P

The structure corresponding to 4 chloro 3 phenylheptanoic acid is,

Organic Chemistry-Package(Custom), Chapter 19, Problem 19.29P , additional homework tip  3

Explanation of Solution

The name of the compound is 4 chloro 3 phenylheptanoic 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,

Organic Chemistry-Package(Custom), Chapter 19, Problem 19.29P , additional homework tip  4

Figure 2

Conclusion

The structure of 4 chloro 3 phenylheptanoic acid is drawn in Figure 2.

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 theparent 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.

Expert Solution
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Answer to Problem 19.29P

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

Organic Chemistry-Package(Custom), Chapter 19, Problem 19.29P , additional homework tip  5

Explanation of Solution

The name of the compound is (R)2 chloropropanoic 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 prioritizedon the basis ofatomic 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,

Organic Chemistry-Package(Custom), Chapter 19, Problem 19.29P , additional homework tip  6

Figure 3

Conclusion

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

Interpretation Introduction

(d)

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 theparent 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.

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Answer to Problem 19.29P

The structure corresponding to β,β dichloropropanoic acid is,

Organic Chemistry-Package(Custom), Chapter 19, Problem 19.29P , additional homework tip  7

Explanation of Solution

The name of the compound is β,β dichloropropanoic acid. The name suggests that the longest carbon chain consists of three carbon atoms. Two chlorine groups are attached to the third carbon atom.

Therefore, the structure corresponding to the given name is,

Organic Chemistry-Package(Custom), Chapter 19, Problem 19.29P , additional homework tip  8

Figure 4

Conclusion

The structure of β,β dichloropropanoic acidis drawn in Figure 4.

Interpretation Introduction

(e)

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 theparent 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.

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Answer to Problem 19.29P

The structure corresponding to m hydroxybenzoic acid is,

Organic Chemistry-Package(Custom), Chapter 19, Problem 19.29P , additional homework tip  9

Explanation of Solution

The name of the compound is m hydroxybenzoic 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,

Organic Chemistry-Package(Custom), Chapter 19, Problem 19.29P , additional homework tip  10

Figure 5

Conclusion

The structure of m hydroxybenzoic acid is drawn in Figure 5.

Interpretation Introduction

(f)

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 theparent 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.

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Answer to Problem 19.29P

The structure corresponding to o chlorobenzoic acid is,

Organic Chemistry-Package(Custom), Chapter 19, Problem 19.29P , additional homework tip  11

Explanation of Solution

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

Organic Chemistry-Package(Custom), Chapter 19, Problem 19.29P , additional homework tip  12

Figure 6

Conclusion

The structure of o chlorobenzoic acidis drawn in Figure 6.

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 theparent 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.

Expert Solution
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Answer to Problem 19.29P

The structure corresponding topotassium acetate is,

Organic Chemistry-Package(Custom), Chapter 19, Problem 19.29P , additional homework tip  13

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,

Organic Chemistry-Package(Custom), Chapter 19, Problem 19.29P , additional homework tip  14

Figure 7

Conclusion

The structure of potassium acetate is drawn in Figure 7.

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 theparent 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.

Expert Solution
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Answer to Problem 19.29P

The structure corresponding tosodium α bromobutyrate is,

Organic Chemistry-Package(Custom), Chapter 19, Problem 19.29P , additional homework tip  15

Explanation of Solution

The name of the compound is sodium α bromobutyrate. 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,

Organic Chemistry-Package(Custom), Chapter 19, Problem 19.29P , additional homework tip  16

Figure 8

Conclusion

The structure of sodium α bromobutyrateis drawn in Figure 8.

Interpretation Introduction

(i)

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 theparent 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.

Expert Solution
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Answer to Problem 19.29P

The structure corresponding to 2,2 dichloropentanedioic acid is,

Organic Chemistry-Package(Custom), Chapter 19, Problem 19.29P , additional homework tip  17

Explanation of Solution

The name of the compound is 2,2 dichloropentanedioic 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,

Organic Chemistry-Package(Custom), Chapter 19, Problem 19.29P , additional homework tip  18

Figure 9

Conclusion

The structure of 2,2 dichloropentanedioic acid is drawn in Figure 9.

Interpretation Introduction

(j)

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 theparent 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.

Expert Solution
Check Mark

Answer to Problem 19.29P

The structure corresponding to 4 isopropyl 2 methyloctanedioic acid is,

Organic Chemistry-Package(Custom), Chapter 19, Problem 19.29P , additional homework tip  19

Explanation of Solution

The name of the compound is 4 isopropyl 2 methyloctanedioic 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,

Organic Chemistry-Package(Custom), Chapter 19, Problem 19.29P , additional homework tip  20

Figure 10

Conclusion

The structure of 4 isopropyl 2 methyloctanedioic acid 2,2 dichloropentanedioic acid is drawn in Figure 10.

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Chapter 19 Solutions

Organic Chemistry-Package(Custom)

Ch. 19 - Prob. 19.11PCh. 19 - Draw the products of each acid-base reaction.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 - Rank the compounds in each group in order of...Ch. 19 - Rank the compounds in each group in order of...Ch. 19 - Prob. 19.18PCh. 19 - Which of the following pairs of compounds can be...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. 19.24PCh. 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. 19.27PCh. 19 - Give the IUPAC name for each compound. a....Ch. 19 - Prob. 19.29PCh. 19 - Draw the structures and give the IUPAC names for...Ch. 19 - Prob. 19.31PCh. 19 - Rank the compounds in each group 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 - Draw the products of each acid-base reaction, and...Ch. 19 - Which compound in each pair has the lower pKa?...Ch. 19 - 19.38 Rank the compounds in each group in order of...Ch. 19 - 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 - Explain the following result. Acetic acid...Ch. 19 - 19.50 Draw all resonance structures of the...Ch. 19 - As we will see in Chapter 23, CH bonds are...Ch. 19 - Prob. 19.51PCh. 19 - The pKa of acetamide (CH3CONH2) is 16. Draw the...Ch. 19 - 19.54 Write out the steps needed to separate...Ch. 19 - Prob. 19.54PCh. 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 - Prob. 19.60PCh. 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 - Prob. 19.71PCh. 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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