Organic Chemistry-Package(Custom)
Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 21, Problem 21.43P

Give the structure corresponding to each name.

a. 2-methyl-3-phenylbutanal e. 3-benzoylcyclopentanone i. 2-sec-butyl-3-cyclopentenone

b. dipropyl ketone f. 2-formylcyclopentanone j. 5, 6-dimethyl-1-cyclohexenecarbaldehyde

c. 3, 3-dimethylcyclohexanecarbaldehyde g. ( 3 R ) -3-methyl-2-heptanone

d. α- methoxypropionaldehyde h. m -acetylbenzaldehyde

Expert Solution
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Interpretation Introduction

(a)

Interpretation: The structure corresponding to 2methyl3phenylbutanal is to be drawn.

Concept introduction: The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing structural formula from IUPAC are:

• First identify the word root for the given compound.

• The suffix used in the compound like –ene.

• Identify the position, location, and number of the substituent bonded to the carbon chain.

Answer to Problem 21.43P

The structure corresponding to 2methyl3phenylbutanal is shown below.

Organic Chemistry-Package(Custom), Chapter 21, Problem 21.43P , additional homework tip  1

Explanation of Solution

The given name is 2methyl3phenylbutanal. The word root used in this is but. It means structure contains four carbon atoms. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. One methyl substituent is attached to the second carbon atom and one phenyl substituent is attached to the third carbon atom. The functional group present in the given compound is aldehyde (CHO). The suffix used for aldehyde is –al.

The structure corresponding to 2methyl3phenylbutanal is shown below.

Organic Chemistry-Package(Custom), Chapter 21, Problem 21.43P , additional homework tip  2

Figure 1

Conclusion

The structure corresponding to 2methyl3phenylbutanal is shown in Figure 1.

Expert Solution
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Interpretation Introduction

(b)

Interpretation: The structure corresponding to dipropyl ketone is to be drawn.

Concept introduction: The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing structural formula from IUPAC are:

• First identify the word root for the given compound.

• The suffix used in the compound like –ene.

• Identify the position, location, and number of the substituent bonded to the carbon chain.

Answer to Problem 21.43P

The structure corresponding to dipropyl ketone is shown below.

Organic Chemistry-Package(Custom), Chapter 21, Problem 21.43P , additional homework tip  3

Explanation of Solution

The given name is dipropyl ketone. The word root used in this is diprop. It means structure contains two propyl groups. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. The functional group present in the given compound is ketone (CO). The suffix used for ketone is -one.

The structure corresponding to dipropyl ketone is shown below.

Organic Chemistry-Package(Custom), Chapter 21, Problem 21.43P , additional homework tip  4

Figure 2

Conclusion

The structure corresponding to dipropyl ketone is shown in Figure 2.

Expert Solution
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Interpretation Introduction

(c)

Interpretation: The structure corresponding to 3,3dimethylcycohexanecarbaldehyde is to be drawn.

Concept introduction: The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing structural formula from IUPAC are:

• First identify the word root for the given compound.

• The suffix used in the compound like –ene.

• Identify the position, location, and number of the substituent bonded to the carbon chain.

Answer to Problem 21.43P

The structure corresponding to 3,3dimethylcycohexanecarbaldehyde is shown below.

Organic Chemistry-Package(Custom), Chapter 21, Problem 21.43P , additional homework tip  5

Explanation of Solution

The given name is 3,3dimethylcycohexanecarbaldehyde. The word root used in this is cyclohex. It means structure contains cyclic ring with six carbon atoms. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. Two methyl substituents are attached to the third carbon atom. The functional group present in the given compound is aldehyde (CHO). The suffix used for aldehyde is –al.

The structure corresponding to 3,3dimethylcycohexanecarbaldehyde is shown below.

Organic Chemistry-Package(Custom), Chapter 21, Problem 21.43P , additional homework tip  6

Figure 3

Conclusion

The structure corresponding to 3,3dimethylcycohexanecarbaldehyde is shown in Figure 3.

Expert Solution
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Interpretation Introduction

(d)

Interpretation: The structure corresponding to α- methoxypropionaldehyde is to be drawn.

Concept introduction: The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing structural formula from IUPAC are:

• First identify the word root for the given compound.

• The suffix used in the compound like –ene.

• Identify the position, location, and number of the substituent bonded to the carbon chain.

Answer to Problem 21.43P

The structure corresponding to α- methoxypropionaldehyde is shown below.

Organic Chemistry-Package(Custom), Chapter 21, Problem 21.43P , additional homework tip  7

Explanation of Solution

The given name is α- methoxypropionaldehyde. The word root used in this is prop. It means structure contains three carbon atoms. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. One methoxy substituent is attached to the alpha carbon atom. The functional group present in the given compound is aldehyde (CHO). The suffix used for aldehyde is –al.

The structure corresponding to α- methoxypropionaldehyde is shown below.

Organic Chemistry-Package(Custom), Chapter 21, Problem 21.43P , additional homework tip  8

Figure 4

Conclusion

The structure corresponding to is shown in Figure 4.

Expert Solution
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Interpretation Introduction

(e)

Interpretation: The structure corresponding to 3benzoylcyclopentanone is to be drawn.

Concept introduction: The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing structural formula from IUPAC are:

• First identify the word root for the given compound.

• The suffix used in the compound like –ene.

• Identify the position, location, and number of the substituent bonded to the carbon chain.

Answer to Problem 21.43P

The structure corresponding to 3benzoylcyclopentanone is shown below.

Organic Chemistry-Package(Custom), Chapter 21, Problem 21.43P , additional homework tip  9

Explanation of Solution

The given name is 3benzoylcyclopentanone. The word root used in this is cyclopent. It means structure contains cyclic ring of five carbon atoms. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. One benzoyl substituent is attached to the third carbon atom. The functional group present in the given compound is ketone (CO). The suffix used for ketone is –one.

The structure corresponding to 3benzoylcyclopentanone is shown below.

Organic Chemistry-Package(Custom), Chapter 21, Problem 21.43P , additional homework tip  10

Figure 5

Conclusion

The structure corresponding to 3benzoylcyclopentanone is shown in Figure 5.

Expert Solution
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Interpretation Introduction

(f)

Interpretation: The structure corresponding to 2formylcyclopentanone is to be drawn.

Concept introduction: The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing structural formula from IUPAC are:

• First identify the word root for the given compound.

• The suffix used in the compound like –ene.

• Identify the position, location, and number of the substituent bonded to the carbon chain.

Answer to Problem 21.43P

The structure corresponding to 2formylcyclopentanone is shown below.

Organic Chemistry-Package(Custom), Chapter 21, Problem 21.43P , additional homework tip  11

Explanation of Solution

The given name is 2formylcyclopentanone. The word root used in this is cyclopent. It means structure contains cyclic ring consisting of five carbon atoms. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. The functional groups present in the given compound are aldehyde (CHO) and ketone (CO). The suffix used for aldehyde is –al and for ketone is –one.

The structure corresponding to 2formylcyclopentanone is shown below.

Organic Chemistry-Package(Custom), Chapter 21, Problem 21.43P , additional homework tip  12

Figure 6

Conclusion

The structure corresponding to 2formylcyclopentanone is shown in Figure 6.

Expert Solution
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Interpretation Introduction

(g)

Interpretation: The structure corresponding to (3R)3methyl-2-heptanone is to be drawn.

Concept introduction: The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing structural formula from IUPAC are:

• First identify the word root for the given compound.

• The suffix used in the compound like –ene.

• Identify the position, location, and number of the substituent bonded to the carbon chain.

Answer to Problem 21.43P

The structure corresponding to (3R)3methyl-2-heptanone is shown below.

Organic Chemistry-Package(Custom), Chapter 21, Problem 21.43P , additional homework tip  13

Explanation of Solution

The given name is -3-(3R)3methyl-2-heptanone. The word root used in this is hept. It means the structure contains seven carbon atoms. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. One methyl substituent is attached to the third carbon atom. The functional group present in the given compound is ketone (CO). The suffix used for ketone is –one. The configuration of methyl group that is attached to the third carbon atom is (R).

The structure corresponding to (3R)3methyl-2-heptanone is shown below.

Organic Chemistry-Package(Custom), Chapter 21, Problem 21.43P , additional homework tip  14

Figure 7

Conclusion

The structure corresponding to (R)3methylheptan2one is shown in Figure 7.

Expert Solution
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Interpretation Introduction

(h)

Interpretation: The structure corresponding to macetylbenzaldehyde is to be drawn.

Concept introduction: The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing structural formula from IUPAC are:

• First identify the word root for the given compound.

• The suffix used in the compound like –ene.

• Identify the position, location, and number of the substituent bonded to the carbon chain.

Answer to Problem 21.43P

The structure corresponding to macetylbenzaldehyde is shown below.

Organic Chemistry-Package(Custom), Chapter 21, Problem 21.43P , additional homework tip  15

Explanation of Solution

The given name is macetylbenzaldehyde. In the given compound, one benzaldehyde group is present. One acetyl substituent is attached to the third carbon atom. The functional groups present in the given compound are aldehyde and ketone.

The structure corresponding to macetylbenzaldehyde is shown below.

Organic Chemistry-Package(Custom), Chapter 21, Problem 21.43P , additional homework tip  16

Figure 8

Conclusion

The structure corresponding to macetylbenzaldehyde is shown in Figure 8.

Expert Solution
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Interpretation Introduction

(i)

Interpretation: The structure corresponding to 2secbutyl-3-cyclopentenone is to be drawn.

Concept introduction: The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing structural formula from IUPAC are:

• First identify the word root for the given compound.

• The suffix used in the compound like –ene.

• Identify the position, location, and number of the substituent bonded to the carbon chain.

Answer to Problem 21.43P

The structure corresponding to 2secbutyl-3-cyclopentenone is shown below.

Organic Chemistry-Package(Custom), Chapter 21, Problem 21.43P , additional homework tip  17

Explanation of Solution

The given name is 2secbutyl-3-cyclopentenone. The word root used in this is cyclopent. It means structure contains cyclic ring consisting of five carbon atoms. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. One secondary butyl substituent is attached to the second carbon atom. The functional groups present in the given compound are aldehyde (CHO) and ketone (CO). The suffix used for aldehyde is –al and for ketone is –one.

In the given compound, one benzaldehyde group is present. The functional group present in the given compound is ketone.

The structure corresponding to 2secbutyl-3-cyclopentenone is shown below.

Organic Chemistry-Package(Custom), Chapter 21, Problem 21.43P , additional homework tip  18

Figure 9

Conclusion

The structure corresponding to 2secbutylcyclopent3enone is shown in Figure 9.

Expert Solution
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Interpretation Introduction

(j)

Interpretation: The structure corresponding to 5,6dimethylcyclohex1enecarbaldehyde is to be drawn.

Concept introduction: The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing structural formula from IUPAC are:

• First identify the word root for the given compound.

• The suffix used in the compound like –ene.

• Identify the position, location, and number of the substituent bonded to the carbon chain.

Answer to Problem 21.43P

The structure corresponding to 5,6dimethyl1cyclohexenecarbaldehyde is shown below.

Organic Chemistry-Package(Custom), Chapter 21, Problem 21.43P , additional homework tip  19

Explanation of Solution

The given name is 5,6dimethyl1cyclohexenecarbaldehyde. The word root used in this is cyclohex. It means the structure contains cyclic ring consisting of six carbon atoms. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. One methyl substituent is attached to the fifth and sixth carbon atom. The functional groups present in the given compound is aldehyde (CHO). The suffix used for aldehyde is –al.

The structure corresponding to 5,6dimethyl1cyclohexenecarbaldehyde is shown below.

Organic Chemistry-Package(Custom), Chapter 21, Problem 21.43P , additional homework tip  20

Figure 10

Conclusion

The structure corresponding to 5,6dimethyl1cyclohexenecarbaldehyde is shown in Figure 10.

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Chapter 21 Solutions

Organic Chemistry-Package(Custom)

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 - Prob. 21.17PCh. 21 - Outline a synthesis of each Wittig reagent from...Ch. 21 - Draw the products including stereoisomers formed...Ch. 21 - Prob. 21.20PCh. 21 - Prob. 21.21PCh. 21 - Show two methods to synthesize each alkene: a...Ch. 21 - Problem 21.22 The product formed when reacts with...Ch. 21 - What 1 amine and carbonyl compound are needed to...Ch. 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 - Problem 21.35 How would you use a protecting group...Ch. 21 - Prob. 21.35PCh. 21 - Problem 21.37 Two naturally occurring compounds...Ch. 21 - Problem 21.38 Draw the products of each...Ch. 21 - Prob. 21.38PCh. 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. 21.41PCh. 21 - Give the IUPAC name for each compound. a. d. g. b....Ch. 21 - Give the structure corresponding to each name. a....Ch. 21 - Including stereoisomers, draw the 11 aldehydes...Ch. 21 - Prob. 21.45PCh. 21 - Prob. 21.46PCh. 21 - What alkyl halide is needed to prepare each Wittig...Ch. 21 - 21.46 Draw the products of each reaction. a. e....Ch. 21 - Prob. 21.49PCh. 21 - Prob. 21.50PCh. 21 - Prob. 21.51PCh. 21 - Prob. 21.52PCh. 21 - Prob. 21.53PCh. 21 - Rank the following compounds in order of...Ch. 21 - Which compound forms the higher concentration of...Ch. 21 - Prob. 21.56PCh. 21 - What Wittig reagent and carbonyl compound are...Ch. 21 - Prob. 21.58PCh. 21 - What reagents are needed to convert each compound...Ch. 21 - What reagents are needed to convert each compound...Ch. 21 - Prob. 21.61PCh. 21 - Devise a synthesis of each alkene using a Wittig...Ch. 21 - Devise a synthesis of each compound from...Ch. 21 - Prob. 21.64PCh. 21 - Prob. 21.65PCh. 21 - Prob. 21.66PCh. 21 - Prob. 21.67PCh. 21 - Prob. 21.68PCh. 21 - Prob. 21.69PCh. 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. 21.72PCh. 21 - 21.67 Draw a stepwise mechanism for each...Ch. 21 - 21.68 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 21.75PCh. 21 - Prob. 21.76PCh. 21 - Prob. 21.77PCh. 21 - Prob. 21.78PCh. 21 - Prob. 21.79PCh. 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. 21.86PCh. 21 - -D-Glucose, a hemiacetal, can be converted to a...Ch. 21 - 21.81 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 21.89PCh. 21 - Prob. 21.90PCh. 21 - Prob. 21.91PCh. 21 - 21.86 Draw stepwise mechanism for the following...
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