ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 21, Problem 21.6P
Interpretation Introduction

(a)

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

Concept introduction: One should follow the given two steps to derive the corresponding structure of a ketone from its common name. The first step is identification of alkyl group that common name suggests. The second step is connecting these groups with C=O bond.

Expert Solution
Check Mark

Answer to Problem 21.6P

The structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 21, Problem 21.6P , additional homework tip  1

Explanation of Solution

The given name is sec-butyl ethyl ketone.

One should follow the given two steps to derive the corresponding structure of a ketone from its common name. The first step is identification of alkyl group that common name suggests. The second step is connecting these groups with C=O bond.

The given name suggests that sec-butyl and ethyl groups are bonded to C=O bond.

Thus, the structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 21, Problem 21.6P , additional homework tip  2

Figure 1

Conclusion

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

Interpretation Introduction

(b)

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

Concept introduction: One should follow the given two steps to derive the corresponding structure of a ketone from its common name. The first step is identification of alkyl group that common name suggests. The second step is connecting these groups with C=O bond.

Expert Solution
Check Mark

Answer to Problem 21.6P

The structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 21, Problem 21.6P , additional homework tip  3

Explanation of Solution

The given name is methyl vinyl ketone.

One should follow the given two steps to derive the corresponding structure of a ketone from its common name. The first step is identification of alkyl group that common name suggests. The second step is connecting these groups with C=O bond.

The given name suggests that methyl and vinyl groups are bonded to C=O bond.

Thus, the structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 21, Problem 21.6P , additional homework tip  4

Figure 2

Conclusion

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

Interpretation Introduction

(c)

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

Concept introduction: One should follow the given two steps to derive the corresponding structure of a ketone from its common name. The first step is identification of alkyl group that common name suggests. The second step is connecting these groups with C=O bond. However, some exceptions of this convention are acetone, acetophenone, and benzophenone.

Expert Solution
Check Mark

Answer to Problem 21.6P

The structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 21, Problem 21.6P , additional homework tip  5

Explanation of Solution

The given name is p-ethylacetophenone.

One should follow the given two steps to derive the corresponding structure of a ketone from its common name. The first step is identification of alkyl group that common name suggests. The second step is connecting these groups with C=O bond. However, some exceptions of this convention are acetone, acetophenone, and benzophenone.

The given name suggests the presence of acetophenone, whose structure is,

ORGANIC CHEMISTRY, Chapter 21, Problem 21.6P , additional homework tip  6

Figure 3

Since the ethyl group is present at para position, the structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 21, Problem 21.6P , additional homework tip  7

Figure 4

Conclusion

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

Interpretation Introduction

(d)

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

Concept introduction: One should follow the given two steps to derive the corresponding structure of a cyclic ketone from its common name. The first step is identification of substituents bonded to it. The second step is connecting these groups at appropriate positions, by placing the carbon of C=O bond at C1.

Expert Solution
Check Mark

Answer to Problem 21.6P

The structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 21, Problem 21.6P , additional homework tip  8

Explanation of Solution

The given name is 3-benzoyl-2-benzylcyclopentanone.

One should follow the given two steps to derive the corresponding structure of a cyclic ketone from its common name. The first step is identification of substituents bonded to it. The second step is connecting these groups at appropriate positions, by placing the carbon of C=O bond at C1.

The given name suggests the presence of cyclic ring containing five carbon atoms, on which C=O bond is present at C1, benzyl group is present at C2, and benzoyl group is present at C3.

Thus, the structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 21, Problem 21.6P , additional homework tip  9

Figure 5

Conclusion

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

Interpretation Introduction

(e)

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

Concept introduction: One should follow the given two steps to derive the corresponding structure of a cyclic enone from its common name. The first step is identification of substituents bonded to it and position of double bond. The second step is connecting the groups at appropriate positions, by placing the carbon of C=O bond at C1.

Expert Solution
Check Mark

Answer to Problem 21.6P

The structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 21, Problem 21.6P , additional homework tip  10

Explanation of Solution

The given name is 6,6-dimethylcyclohex-2-enone.

One should follow the given two steps to derive the corresponding structure of a cyclic enone from its common name. The first step is identification of substituents bonded to it and position of double bond. The second step is connecting the groups at appropriate positions, by placing the carbon of C=O bond at C1.

The given name suggests the presence of cyclic ring containing six carbon atoms, on which C=O bond is present at C1, two methyl groups are present at C6, and C=C bond is present between C2andC3.

Thus, the structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 21, Problem 21.6P , additional homework tip  11

Figure 6

Conclusion

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

Interpretation Introduction

(f)

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

Concept introduction: One should follow the given two steps to derive the corresponding structure of an enal (compound containing both aldehyde and a CC double bond) from its common name. The first step is identification of longest chain and substituents bonded to it along with the position of double bond. The second step is connecting the groups at appropriate positions, by placing the carbon of C=O bond at C1.

Expert Solution
Check Mark

Answer to Problem 21.6P

The structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 21, Problem 21.6P , additional homework tip  12

Explanation of Solution

The given name is 3-ethylhex-5-enal.

One should follow the given two steps to derive the corresponding structure of an enal (compound containing both aldehyde and a CC double bond) from its common name. The first step is identification of longest chain and substituents bonded to it along with the position of double bond. The second step is connecting the groups at appropriate positions, by placing the carbon of C=O bond at C1.

The given name suggests the presence of longest chain containing six carbon atoms, on which C=O bond is present at C1, ethyl group is present at C3, and C=C bond is present between C5andC6.

Thus, the structure corresponding to the given name is,

ORGANIC CHEMISTRY, Chapter 21, Problem 21.6P , additional homework tip  13

Figure 7

Conclusion

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

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Chapter 21 Solutions

ORGANIC CHEMISTRY

Ch. 21 - Prob. 21.11PCh. 21 - Prob. 21.12PCh. 21 - Prob. 21.13PCh. 21 - Prob. 21.14PCh. 21 - Problem 21.15 Draw the product of each...Ch. 21 - Prob. 21.16PCh. 21 - Problem 21.17 Draw the products of the following...Ch. 21 - Problem 21.18 Outline a synthesis of each Wittig...Ch. 21 - Problem 21.19 Draw the products (including...Ch. 21 - Problem 21.20 What starting materials are needed...Ch. 21 - Prob. 21.21PCh. 21 - Problem 21.22 The product formed when reacts with...Ch. 21 - Prob. 21.23PCh. 21 - Prob. 21.24PCh. 21 - Prob. 21.25PCh. 21 - Prob. 21.26PCh. 21 - Prob. 21.27PCh. 21 - Problem 21.28 Draw a stepwise mechanism for the...Ch. 21 - Problem 21.29 Draw the products of each...Ch. 21 - Problem 21.30 Label each compound as an acetal, a...Ch. 21 - Problem 21.31 Draw a stepwise mechanism for the...Ch. 21 - Problem 21.32 Draw the products of each...Ch. 21 - Problem 21.33 Safrole is a naturally occurring...Ch. 21 - Prob. 21.34PCh. 21 - Problem 21.35 How would you use a protecting group...Ch. 21 - Prob. 21.36PCh. 21 - Problem 21.37 Two naturally occurring compounds...Ch. 21 - Problem 21.38 Draw the products of each...Ch. 21 - Prob. 21.39PCh. 21 - Problem 21.40 (a) Give the IUPAC name for A and B....Ch. 21 - 21.41 Rank the following compounds in order of...Ch. 21 - Prob. 21.42PCh. 21 - 21.43 Give the IUPAC name for each compound. a....Ch. 21 - 21.44 Give the structure corresponding to each...Ch. 21 - Prob. 21.45PCh. 21 - 21.46 Draw the products of each reaction. a. e....Ch. 21 - Prob. 21.47PCh. 21 - 21.48 Draw all stereoisomers formed in each...Ch. 21 - Prob. 21.49PCh. 21 - What products are formed when each acetal is...Ch. 21 - Prob. 21.51PCh. 21 - Prob. 21.52PCh. 21 - Which compound forms the higher concentration of...Ch. 21 - Prob. 21.54PCh. 21 - Prob. 21.55PCh. 21 - Prob. 21.56PCh. 21 - Prob. 21.57PCh. 21 - Devise a synthesis of each alkene using a Wittig...Ch. 21 - Devise a synthesis of each compound from...Ch. 21 - Prob. 21.60PCh. 21 - Devise a synthesis of each compound from ethanol...Ch. 21 - Prob. 21.62PCh. 21 - Prob. 21.63PCh. 21 - 21.64 Draw a stepwise mechanism for the following...Ch. 21 - 21.65 Draw a stepwise mechanism f or the following...Ch. 21 - Prob. 21.66PCh. 21 - 21.67 Draw a stepwise mechanism for each...Ch. 21 - 21.68 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 21.69PCh. 21 - Prob. 21.70PCh. 21 - Prob. 21.71PCh. 21 - Prob. 21.72PCh. 21 - 21.73 Although the carbonyl absorption of cyclic...Ch. 21 - 21.74 Use the and data to determine the...Ch. 21 - 21.75 A solution of acetone in ethanol in the...Ch. 21 - Compounds A and B have molecular formula ....Ch. 21 - 21.77 An unknown compound C of molecular formula ...Ch. 21 - 21.78 An unknown compound D exhibits a strong...Ch. 21 - Prob. 21.79PCh. 21 - -D-Glucose, a hemiacetal, can be converted to a...Ch. 21 - 21.81 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 21.82PCh. 21 - 21.83 Draw a stepwise mechanism f or the...Ch. 21 - Prob. 21.84PCh. 21 - Prob. 21.85PCh. 21 - 21.86 Draw stepwise mechanism for the following...
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