ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 22, Problem 22.41P

Give the structure corresponding to each name.

a. cyclohexyl propanoate

b. cyclohexanecarboxamide

c. 4- methylheptanenitrile

d. Vinyl acetate

e. Benzoic propanoic anhydride

f. 3- methylhexanoyl chloride

g. octyl butanoate

h. N, N-dibenzylformamide

Expert Solution
Check Mark
Interpretation Introduction

(a)

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

Concept introduction: One should follow the given steps to draw the structure of a compound from its name. The first step is identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in the direction, where functional group gets a lower number. The third step is addition of substituents at appropriate atoms.

Answer to Problem 22.41P

The structure corresponding to the given name is

ORGANIC CHEMISTRY, Chapter 22, Problem 22.41P , additional homework tip  1

Explanation of Solution

The given name indicates that compound contains ester (name ends with –ate) as the functional group, and propane as the longest carbon chain with one cyclohexyl substitution as OR.

Thus, the structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 22, Problem 22.41P , additional homework tip  2

Figure 1

Conclusion

The structure corresponding to the given name is drawn in Figure 1.

Expert Solution
Check Mark
Interpretation Introduction

(b)

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

Concept introduction: One should follow the given steps to draw the structure of a compound from its name. The first step is identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in the direction, where functional group gets a lower number. The third step is addition of substituents at appropriate atoms.

Answer to Problem 22.41P

The structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 22, Problem 22.41P , additional homework tip  3

Explanation of Solution

The given name indicates that compound contains amide (name ends with -amide) as the functional group. This amide group is derived from cyclohexylcarboxylic acid, and bonded to cyclohexane ring.

Thus, the structure corresponding to given name is,

ORGANIC CHEMISTRY, Chapter 22, Problem 22.41P , additional homework tip  4

Figure 2

Conclusion

The structure corresponding to the given name is drawn in Figure 2.

Expert Solution
Check Mark
Interpretation Introduction

(c)

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

Concept introduction: One should follow the given steps to draw the structure of a compound from its name. The first step is identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in the direction, where functional group gets a lower number. The third step is addition of substituents at appropriate atoms.

Answer to Problem 22.41P

The structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 22, Problem 22.41P , additional homework tip  5

Explanation of Solution

The given name indicates that compound contains cyano (name ends with -nitrile) as the functional group, and heptane as the longest carbon chain with one methyl substitution at C4 position.

Thus, the structure corresponding to given name is,

ORGANIC CHEMISTRY, Chapter 22, Problem 22.41P , additional homework tip  6

Figure 3

Conclusion

The structure corresponding to the given name is drawn in Figure 3.

Expert Solution
Check Mark
Interpretation Introduction

(d)

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

Concept introduction: One should follow the given steps to draw the structure of a compound from its name. The first step is identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in the direction, where functional group gets a lower number. The third step is addition of substituents at appropriate atoms.

Answer to Problem 22.41P

The structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 22, Problem 22.41P , additional homework tip  7

Explanation of Solution

The given name indicates that compound contains ester (name ends with -ate) as the functional group, and an acetate group is bonded to a vinyl group (OR).

Thus, the structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 22, Problem 22.41P , additional homework tip  8

Figure 4

Conclusion

The structure corresponding to the given name is drawn in Figure 4.

Expert Solution
Check Mark
Interpretation Introduction

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

(e)

Concept introduction: One should follow the given steps to draw the structure of a compound from its name. The first step is identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in the direction, where functional group gets a lower number. The third step is addition of substituents at appropriate atoms.

Answer to Problem 22.41P

The structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 22, Problem 22.41P , additional homework tip  9

Explanation of Solution

The given name indicates that compound contains anhydride (name ends with -anhydride) as the functional group. This anhydride compound is derived from benzoic acid and propanoic acid.

Thus, the structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 22, Problem 22.41P , additional homework tip  10

Figure 5

Conclusion

The structure corresponding to the given name is drawn in Figure 5.

Expert Solution
Check Mark
Interpretation Introduction

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

(f)

Concept introduction: One should follow the given steps to draw the structure of a compound from its name. The first step is identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in the direction, where functional group gets a lower number. The third step is addition of substituents at appropriate atoms.

Answer to Problem 22.41P

The structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 22, Problem 22.41P , additional homework tip  11

Explanation of Solution

The given name indicates that compound contains acid chloride (name ends with -yl chloride) as the functional group, and hexane as the longest carbon chain with one methyl substitution at C3 position.

Thus, the structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 22, Problem 22.41P , additional homework tip  12

Figure 6

Conclusion

The structure corresponding to the given name is drawn in Figure 6.

Expert Solution
Check Mark
Interpretation Introduction

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

(g)

Concept introduction: One should follow the given steps to draw the structure of a compound from its name. The first step is identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in the direction, where functional group gets a lower number. The third step is addition of substituents at appropriate atoms.

Answer to Problem 22.41P

The structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 22, Problem 22.41P , additional homework tip  13

Explanation of Solution

The given name indicates that compound contains ester (name ends with –ate) as the functional group, and butane as the longest carbon chain with one octyl substitution as OR.

Thus, the structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 22, Problem 22.41P , additional homework tip  14

Figure 7

Conclusion

The structure corresponding to the given name is drawn in Figure 7.

Expert Solution
Check Mark
Interpretation Introduction

(h)

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

Concept introduction: One should follow the given steps to draw the structure of a compound from its name. The first step is identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in the direction, where functional group gets a lower number. The third step is addition of substituents at appropriate atoms.

Answer to Problem 22.41P

The structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 22, Problem 22.41P , additional homework tip  15

Explanation of Solution

The given name indicates that compound contains amide (name ends with -amide) as the functional group. This amide group is derived from formic acid, and bonded to two benzyl groups.

Thus, the structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 22, Problem 22.41P , additional homework tip  16

Figure 8

Conclusion

The structure corresponding to the given name is drawn in Figure 8.

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Chapter 22 Solutions

ORGANIC CHEMISTRY

Ch. 22 - Prob. 22.11PCh. 22 - Prob. 22.12PCh. 22 - Prob. 22.13PCh. 22 - Prob. 22.14PCh. 22 - Problem 22.15 Draw the products of each...Ch. 22 - Problem 22.16 Draw the products of each reaction. ...Ch. 22 - Prob. 22.17PCh. 22 - Problem 22.18 Draw a stepwise mechanism for the...Ch. 22 - Prob. 22.19PCh. 22 - Problem 22.20 Fenofibrate is a...Ch. 22 - Problem 22.21 What product is formed when the...Ch. 22 - How would you synthesize olestra from sucrose? Ch. 22 - Problem 22.23 What is the composition of the soap...Ch. 22 - Problem 22.24 Draw a stepwise mechanism for the...Ch. 22 - Prob. 22.25PCh. 22 - Problem 22.26 Some penicillins cannot be...Ch. 22 - Prob. 22.27PCh. 22 - Prob. 22.28PCh. 22 - Prob. 22.29PCh. 22 - Problem 22.30 Glucosamine is a dietry supplement...Ch. 22 - Draw the products of each reaction. a. c. b.Ch. 22 - Draw a tautomer of each compound. a. b. c. Ch. 22 - Draw the product of each reaction. a. b.Ch. 22 - Draw the product of each reaction. a. b.Ch. 22 - Prob. 22.35PCh. 22 - Problem 22.36 Outline two different ways that can...Ch. 22 - 22.37 Rank the following compounds in order of...Ch. 22 - Prob. 22.38PCh. 22 - Prob. 22.39PCh. 22 - 22.40 Give the IUPAC or common name for each...Ch. 22 - 22.41 Give the structure corresponding to each...Ch. 22 - Prob. 22.42PCh. 22 - 22.43 Explain why is a stronger acid and a weaker...Ch. 22 - (a) Propose an explanation for the difference in...Ch. 22 - Draw the product formed when phenylacetic acid is...Ch. 22 - Draw the product formed when phenylacetonitrile ...Ch. 22 - 22.47 Draw the organic products formed in each...Ch. 22 - Prob. 22.48PCh. 22 - Prob. 22.49PCh. 22 - Prob. 22.50PCh. 22 - Prob. 22.51PCh. 22 - Prob. 22.52PCh. 22 - Prob. 22.53PCh. 22 - 22.54 Draw a stepwise mechanism f or the following...Ch. 22 - 22.55 When acetic acid () is treated with a trace...Ch. 22 - Prob. 22.56PCh. 22 - Prob. 22.57PCh. 22 - Draw a stepwise mechanism for the following...Ch. 22 - Prob. 22.59PCh. 22 - Prob. 22.60PCh. 22 - Prob. 22.61PCh. 22 - Draw a stepwise mechanism for the following...Ch. 22 - 22.63 Acid-catalyzed hydrolysis of forms compound...Ch. 22 - 22.64 What carboxylic acid and alcohol are needed...Ch. 22 - Problem 22.65 Devise a synthesis of each compound...Ch. 22 - Prob. 22.66PCh. 22 - Prob. 22.67PCh. 22 - Prob. 22.68PCh. 22 - Prob. 22.69PCh. 22 - 22.70 What polyester or poly amide can be prepared...Ch. 22 - 22.71 What two monomers are needed to prepare each...Ch. 22 - Prob. 22.72PCh. 22 - 22.73 How can IR spectroscopy be used to...Ch. 22 - 22.74 Rank the following compounds in order of...Ch. 22 - 22.75 Identify the structures of each compound...Ch. 22 - 22.76 Identify the structures of A and B, isomers...Ch. 22 - Prob. 22.77PCh. 22 - 22.78 Identify the structure of compound C...Ch. 22 - 22.79 Identify the structures of D and E, isomers...Ch. 22 - 22.80 With reference to amides A and B, the...Ch. 22 - Prob. 22.81PCh. 22 - Prob. 22.82PCh. 22 - Prob. 22.83PCh. 22 - Draw a stepwise mechanism for the following...Ch. 22 - Draw a stepwise mechanism for the following...
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