ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 21, Problem 21.4P
Interpretation Introduction

(a)

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

Concept introduction: One should follow the given steps to derive the structure of an aldehyde from its IUPAC name. The first step is finding of longest parent chain that contains an aldehyde group. The second step is changing of -e ending of the parent alkane to the suffix -al. However, when an aldehyde (CHO) group is bonded to a ring then after naming of ring, the suffix -carbaldehyde is used. The third step is numbering of chain or ring by putting the CHO group at C1, and using the general rules of nomenclature.

Expert Solution
Check Mark

Answer to Problem 21.4P

The structure corresponding to the given IUPAC name is,

ORGANIC CHEMISTRY, Chapter 21, Problem 21.4P , additional homework tip  1

Explanation of Solution

The IUPAC name of the given compound is 2-isobutyl-3-isopropylhexanal.

One should follow the given steps to derive the structure of an aldehyde from its IUPAC name. The first step is finding of longest parent chain that contains an aldehyde group. The second step is changing of -e ending of the parent alkane to the suffix -al. However, when an aldehyde (CHO) group is bonded to a ring then after naming of ring, the suffix -carbaldehyde is used. The third step is numbering of chain or ring by putting the CHO group at C1, and using the general rules of nomenclature.

The given IUPAC name suggests the presence of 6C's in the longest chain containing CHO group. On this chain, the isobutyl group is substituted at C2, and the isopropyl group is substituted at C3.

Thus, the structure corresponding to the given IUPAC name is,

ORGANIC CHEMISTRY, Chapter 21, Problem 21.4P , additional homework tip  2

Figure 1

Conclusion

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

Interpretation Introduction

(b)

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

Concept introduction: One should follow the given steps to derive the structure of an aldehyde from its IUPAC name. The first step is finding of longest parent chain that contains an aldehyde group. The second step is changing of -e ending of the parent alkane to the suffix -al. However, when an aldehyde (CHO) group is bonded to a ring then after naming of ring, the suffix -carbaldehyde is used. The third step is numbering of chain or ring by putting the CHO group at C1, and using the general rules of nomenclature.

Expert Solution
Check Mark

Answer to Problem 21.4P

The structure corresponding to the given IUPAC name is,

ORGANIC CHEMISTRY, Chapter 21, Problem 21.4P , additional homework tip  3

Explanation of Solution

The IUPAC name of the given compound is trans-3-methylcyclopentanecrabaldehyde.

One should follow the given steps to derive the structure of an aldehyde from its IUPAC name. The first step is finding of longest parent chain that contains an aldehyde group. The second step is changing of -e ending of the parent alkane to the suffix -al. However, when an aldehyde (CHO) group is bonded to a ring then after naming of ring, the suffix -carbaldehyde is used. The third step is numbering of chain or ring by putting the CHO group at C1, and using the general rules of nomenclature.

The given IUPAC name suggests the presence of 5C's in the ring chain containing CHO group. On this chain, the methyl group is substituted at C3, and present opposite to the aldehyde group. Thus, the structure corresponding to the given IUPAC name is,

ORGANIC CHEMISTRY, Chapter 21, Problem 21.4P , additional homework tip  4

Figure 2

Conclusion

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

Interpretation Introduction

(c)

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

Concept introduction: One should follow the given steps to derive the structure of an aldehyde from its IUPAC name. The first step is finding of longest parent chain that contains an aldehyde group. The second step is changing of -e ending of the parent alkane to the suffix -al. However, when an aldehyde (CHO) group is bonded to a ring then after naming of ring, the suffix -carbaldehyde is used. The third step is numbering of chain or ring by putting the CHO group at C1, and using the general rules of nomenclature.

Expert Solution
Check Mark

Answer to Problem 21.4P

The structure corresponding to the given IUPAC name is,

ORGANIC CHEMISTRY, Chapter 21, Problem 21.4P , additional homework tip  5

Explanation of Solution

The IUPAC name of the given compound is 1-methylcyclopropanecrabaldehyde.

One should follow the given steps to derive the structure of an aldehyde from its IUPAC name. The first step is finding of longest parent chain that contains an aldehyde group. The second step is changing of -e ending of the parent alkane to the suffix -al. However, when an aldehyde (CHO) group is bonded to a ring then after naming of ring, the suffix -carbaldehyde is used. The third step is numbering of chain or ring by putting the CHO group at C1, and using the general rules of nomenclature.

The given IUPAC name suggests the presence of 3C's in the ring chain containing CHO group. On this chain, the methyl group is substituted at C1. Thus, the structure corresponding to the given IUPAC name is,

ORGANIC CHEMISTRY, Chapter 21, Problem 21.4P , additional homework tip  6

Figure 3

Conclusion

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

Interpretation Introduction

(d)

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

Concept introduction: One should follow the given steps to derive the structure of an aldehyde from its IUPAC name. The first step is finding of longest parent chain that contains an aldehyde group. The second step is changing of -e ending of the parent alkane to the suffix -al. However, when an aldehyde (CHO) group is bonded to a ring then after naming of ring, the suffix -carbaldehyde is used. The third step is numbering of chain or ring by putting the CHO group at C1, and using the general rules of nomenclature.

Expert Solution
Check Mark

Answer to Problem 21.4P

The structure corresponding to the given IUPAC name is,

ORGANIC CHEMISTRY, Chapter 21, Problem 21.4P , additional homework tip  7

Explanation of Solution

The IUPAC name of the given compound is 3, 6-diethylnonanal.

One should follow the given steps to derive the structure of an aldehyde from its IUPAC name. The first step is finding of longest parent chain that contains an aldehyde group. The second step is changing of -e ending of the parent alkane to the suffix -al. However, when an aldehyde (CHO) group is bonded to a ring then after naming of ring, the suffix -carbaldehyde is used. The third step is numbering of chain or ring by putting the CHO group at C1, and using the general rules of nomenclature.

The given IUPAC name suggests the presence of 9C's in the longest chain containing CHO group. On this chain, the ethyl groups are substituted both at C3, and C6.

Thus, the structure corresponding to the given IUPAC name is,

ORGANIC CHEMISTRY, Chapter 21, Problem 21.4P , additional homework tip  8

Figure 4

Conclusion

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

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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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