ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 25, Problem 25.39P
Interpretation Introduction

(a)

Interpretation: The structure that corresponds to the given name is to be drawn.

Concept introduction: One should follow the given three steps to derive the structure of the compound from its IUPAC name. The first step involves the identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in either direction. The third step is addition of substituents at appropriate carbon atoms.

Expert Solution
Check Mark

Answer to Problem 25.39P

The structure that corresponds to the given name is,

ORGANIC CHEMISTRY, Chapter 25, Problem 25.39P , additional homework tip  1

Figure 1

Explanation of Solution

The name of the given molecule suggests that a nitrogen atom is bonded to cyclopentane and isobutyl group. Cyclopentane consists of five carbon atoms. Therefore, the structure of the given compound is,

ORGANIC CHEMISTRY, Chapter 25, Problem 25.39P , additional homework tip  2

Figure 1

Conclusion

The structure that corresponds to the given name is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: The structure that corresponds to the given name is to be drawn.

Concept introduction: One should follow the given three steps to derive the structure of the compound from its IUPAC name. The first step involves the identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in either direction. The third step is addition of substituents at appropriate carbon atoms.

Expert Solution
Check Mark

Answer to Problem 25.39P

The structure that corresponds to the given name is,

ORGANIC CHEMISTRY, Chapter 25, Problem 25.39P , additional homework tip  3

Figure 2

Explanation of Solution

The name of the given compound is tri-tert-butylamine. Prefix ‘tri’ shows that a nitrogen atom is bonded to three tert-butyl groups. Therefore, the structure of the given compound is,

ORGANIC CHEMISTRY, Chapter 25, Problem 25.39P , additional homework tip  4

Figure 2

Conclusion

The structure that corresponds to the given name is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation: The structure that corresponds to the given name is to be drawn.

Concept introduction: One should follow the given three steps to derive the structure of the compound from its IUPAC name. The first step involves the identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in either direction. The third step is addition of substituents at appropriate carbon atoms.

Expert Solution
Check Mark

Answer to Problem 25.39P

The structure that corresponds to the given name is,

ORGANIC CHEMISTRY, Chapter 25, Problem 25.39P , additional homework tip  5

Figure 3

Explanation of Solution

The name of the given compound is N, N-diisopropylaniline. Prefix ‘di’ shows that a nitrogen atom is bonded to two isopropyl groups and it is bonded to six membered aromatic ring. Therefore, the structure of the given compound is,

ORGANIC CHEMISTRY, Chapter 25, Problem 25.39P , additional homework tip  6

Figure 3

Conclusion

The structure that corresponds to the given name is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation: The structure that corresponds to the given name is to be drawn.

Concept introduction: One should follow the given three steps to derive the structure of the compound from its IUPAC name. The first step involves the identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in either direction. The third step is addition of substituents at appropriate carbon atoms.

Expert Solution
Check Mark

Answer to Problem 25.39P

The structure that corresponds to the given name is,

ORGANIC CHEMISTRY, Chapter 25, Problem 25.39P , additional homework tip  7

Figure 4

Explanation of Solution

The name of the given compound is N-methylpyrrole. Pyrrole is the parent chain of the given compound. It is an aromatic five membered ring which contains nitrogen atom and two double bonds. The nitrogen atom is bonded to methyl group. Therefore, the structure of the given compound is,

ORGANIC CHEMISTRY, Chapter 25, Problem 25.39P , additional homework tip  8

Figure 4

Conclusion

The structure that corresponds to the given name is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation: The structure that corresponds to the given name is to be drawn.

Concept introduction: One should follow the given three steps to derive the structure of the compound from its IUPAC name. The first step involves the identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in either direction. The third step is addition of substituents at appropriate carbon atoms.

Expert Solution
Check Mark

Answer to Problem 25.39P

The structure that corresponds to the given name is,

ORGANIC CHEMISTRY, Chapter 25, Problem 25.39P , additional homework tip  9

Figure 5

Explanation of Solution

The name of the given compound is N-methylcyclopentanamine. The name suggests that nitrogen atom is bonded to cyclopentane and methyl group. Therefore, the structure of the given compound is,

ORGANIC CHEMISTRY, Chapter 25, Problem 25.39P , additional homework tip  10

Figure 5

Conclusion

The structure that corresponds to the given name is shown in Figure 5.

Interpretation Introduction

(f)

Interpretation: The structure that corresponds to the given name is to be drawn.

Concept introduction: One should follow the given three steps to derive the structure of the compound from its IUPAC name. The first step involves the identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in either direction. The third step is addition of substituents at appropriate carbon atoms.

Expert Solution
Check Mark

Answer to Problem 25.39P

The structure that corresponds to the given name is,

ORGANIC CHEMISTRY, Chapter 25, Problem 25.39P , additional homework tip  11

Figure 6

Explanation of Solution

The name of the given compound is 3-methylhexan-2-amine. The name of the compound suggests that the amine group is present on second carbon atom and methyl group is present on third carbon atom on a chain of six carbon atoms. Therefore, the structure of the given compound is,

ORGANIC CHEMISTRY, Chapter 25, Problem 25.39P , additional homework tip  12

Figure 6

Conclusion

The structure that corresponds to the given name is shown in Figure 6.

Interpretation Introduction

(g)

Interpretation: The structure that corresponds to the given name is to be drawn.

Concept introduction: One should follow the given three steps to derive the structure of the compound from its IUPAC name. The first step involves the identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in either direction. The third step is addition of substituents at appropriate carbon atoms.

Expert Solution
Check Mark

Answer to Problem 25.39P

The structure that corresponds to the given name is,

ORGANIC CHEMISTRY, Chapter 25, Problem 25.39P , additional homework tip  13

Figure 7

Explanation of Solution

The name of the given compound is 2-sec-butylpiperidine. Piperidine is the parent chain of the given compound. It is a five membered cyclic compound which contains nitrogen atom. The carbon atom present adjacent to nitrogen atom is bonded to sec-butyl. Therefore, the structure of the given compound is,

ORGANIC CHEMISTRY, Chapter 25, Problem 25.39P , additional homework tip  14

Figure 7

Conclusion

The structure that corresponds to the given name is shown in Figure 7.

Interpretation Introduction

(h)

Interpretation: The structure that corresponds to the given name is to be drawn.

Concept introduction: One should follow the given three steps to derive the structure of the compound from its IUPAC name. The first step involves the identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in either direction. The third step is addition of substituents at appropriate carbon atoms.

Expert Solution
Check Mark

Answer to Problem 25.39P

The structure that corresponds to the given name is,

ORGANIC CHEMISTRY, Chapter 25, Problem 25.39P , additional homework tip  15

Figure 8

Explanation of Solution

The name of the given compound is (S)-heptan-2-amine. The name of the compound suggests that the amine group is present on second carbon atom on a chain of seven carbon atoms. Therefore, the structure of the given compound is,

ORGANIC CHEMISTRY, Chapter 25, Problem 25.39P , additional homework tip  16

Figure 8

Conclusion

The structure that corresponds to the given name is shown in Figure 8.

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Chapter 25 Solutions

ORGANIC CHEMISTRY

Ch. 25 - Prob. 25.11PCh. 25 - Prob. 25.12PCh. 25 - Prob. 25.13PCh. 25 - Prob. 25.14PCh. 25 - Prob. 25.15PCh. 25 - Prob. 25.16PCh. 25 - Prob. 25.17PCh. 25 - Problem 25.18 Write out steps to show how each of...Ch. 25 - Prob. 25.19PCh. 25 - Prob. 25.20PCh. 25 - Prob. 25.21PCh. 25 - Problem 25.22 Which nitrogen atom in each compound...Ch. 25 - Prob. 25.23PCh. 25 - Prob. 25.24PCh. 25 - Prob. 25.25PCh. 25 - Prob. 25.26PCh. 25 - Prob. 25.27PCh. 25 - Problem 25.28 Draw the major product formed in...Ch. 25 - Prob. 25.29PCh. 25 - Prob. 25.30PCh. 25 - Problem 25.31 Devise a synthesis of each compound...Ch. 25 - Prob. 25.32PCh. 25 - Problem 25.33 What starting materials are needed...Ch. 25 - Problem 25.34 (a) What two components are needed...Ch. 25 - Prob. 25.35PCh. 25 - Prob. 25.36PCh. 25 - 25.37 Varenicline (trade name Chantix) is a drug...Ch. 25 - Give a systematic or common name for each...Ch. 25 - Prob. 25.39PCh. 25 - 25.40 How many stereogenic centers are present in...Ch. 25 - 25.41 Rank the compounds in each group in order of...Ch. 25 - 25.42 Decide which atom in each molecule is most...Ch. 25 - 25.43 Explain why pyrimidine is less basic than...Ch. 25 - 25.44 Rank the nitrogen atoms in each compound in...Ch. 25 - 25.45 Explain why nitroaniline is a stronger base...Ch. 25 - 25.46 Explain the observed difference in the...Ch. 25 - 25.47 Why is pyrrole more acidic than...Ch. 25 - Prob. 25.48PCh. 25 - Prob. 25.49PCh. 25 - Prob. 25.50PCh. 25 - 25.51 How would you separate toluene , benzoic...Ch. 25 - 25.52 Draw the products formed when methylaniline ...Ch. 25 - Prob. 25.53PCh. 25 - Prob. 25.54PCh. 25 - 25.55 Draw the organic products formed in each...Ch. 25 - Prob. 25.56PCh. 25 - 25.57 Identify A, B, and C, three intermediates in...Ch. 25 - Prob. 25.58PCh. 25 - Prob. 25.59PCh. 25 - 25.60 A chiral amine A having the configuration...Ch. 25 - 25.61 Draw a stepwise mechanism for each...Ch. 25 - 25.62 Draw a stepwise mechanism for the following...Ch. 25 - Prob. 25.63PCh. 25 - 25.64 Tertiary aromatic amines react with and ...Ch. 25 - 25.65 Devise a synthesis of each compound from...Ch. 25 - Prob. 25.66PCh. 25 - Prob. 25.67PCh. 25 - Prob. 25.68PCh. 25 - Prob. 25.69PCh. 25 - 25.70 Devise a synthesis of each biologically...Ch. 25 - 25.71 Devise a synthesis of each compound from...Ch. 25 - 25.72 Three isomeric compounds A, B, and C, all...Ch. 25 - 25.73 Treatment of compound D with LiAlH4 followed...Ch. 25 - Prob. 25.74PCh. 25 - 25.75 Rank the following compounds in order of...Ch. 25 - Prob. 25.76PCh. 25 - Prob. 25.77PCh. 25 - Prob. 25.78P
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