ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 4, Problem 4.40P

Draw the structure corresponding to each IUPAC name.

a. 3 ethyl 2 methylhexane

b. sec butylcyclopentane

c. 4 isopropyl 2 , 4 , 5 trimethylundecane

d. cyclobutylcycloheptane

e. 3 ethyl 1 , 1 dimethylcyclohexane

f. 4 butyl 1 , 1 diethylcycloocatne

g 6 isopropyl 2 , 3 dimethylocatne

h. 2 , 2 , 6 , 6 , 7 pentamethylocatne

i. c i s 1 ethyl 3 methylcyclopentane

j. t r a n s 1 t e r t butyl 4 ethylcycloheaxne

Expert Solution
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Interpretation Introduction

(a)

Interpretation: The structure corresponding to 3ethyl2methylhexane is to be drawn.

Concept introduction: The systematic naming of organic compound is given by IUPAC nomenclature. 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:

1. First identify the word root for the given compound.

2. The suffix used in the compound like –ene.

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

Answer to Problem 4.40P

The structure corresponding to 3ethyl2methylhexane is shown as,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.40P , additional homework tip  1

Explanation of Solution

The given IUPAC name is 3ethyl2methylhexane.

Rules for writing structural formula from IUPAC are

1. First identify the word root for the given compound.

2. The suffix used in the compound like –ene.

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

The given name is 3ethyl2methylhexane. The word root used in this is hex. It means structure contains six carbon atoms. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. Therefore, the name suggests that one isopropyl substituents is attached to the third carbon atom and one methyl substituent is attached to second carbon atom.

Thus, the correct structure of 3ethyl2methylhexane is shown below.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.40P , additional homework tip  2

Figure 1

Conclusion

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

Expert Solution
Check Mark
Interpretation Introduction

(b)

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

Concept introduction: The systematic naming of organic compound is given by IUPAC nomenclature. 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:

4. First identify the word root for the given compound.

5. The suffix used in the compound like –ene.

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

Answer to Problem 4.40P

The structure corresponding to secbutylcyclopentane is shown as,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.40P , additional homework tip  3

Explanation of Solution

The given IUPAC name is secbutylcyclopentane.

The given name is secbutylcyclopentane. The word root used in this is pent. It means structure contains five carbon atoms. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. Therefore, the name suggests that one butyl substituents is attached to the second carbon atom of pentane. Thus, the correct structure of secbutylcyclopentane is shown below.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.40P , additional homework tip  4

Figure 2

Conclusion

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

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The structure corresponding to 4isopropyl2,4,5trimethylheptane is to be drawn.

Concept introduction: The systematic naming of organic compound is given by IUPAC nomenclature. 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:

1. First identify the word root for the given compound.

2. The suffix used in the compound like –ene.

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

Answer to Problem 4.40P

The structure corresponding to 4isopropyl2,4,5trimethylheptane is shown as,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.40P , additional homework tip  5

Explanation of Solution

The given IUPAC name is 4isopropyl2,4,5trimethylheptane.

The given name is 4isopropyl2,4,5trimethylheptane. The word root used in this is hept. It means 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. Therefore, the name suggests that one methyl substituents are attached to the second, fourth and fifth carbon atom and one isopropyl substituent is attached to fourth carbon atom.

Thus, the correct structure of 4isopropyl2,4,5trimethylheptane is shown below.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.40P , additional homework tip  6

Figure 3

Conclusion

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

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The structure corresponding to cyclobutylcycloheptane 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.

Answer to Problem 4.40P

The structure corresponding to cyclobutylcycloheptane is shown as,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.40P , additional homework tip  7

Explanation of Solution

The given IUPAC name is cyclobutylcycloheptane. The given name is cyclobutylcycloheptane. The word root used in this is hept. It means 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. Therefore, the name suggests that one cyclobutyl substituents is attached to the carbon atom of cycloheptane.

Thus, the correct structure of cyclobutylcycloheptane is shown below.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.40P , additional homework tip  8

Figure 4

Conclusion

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

Expert Solution
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Interpretation Introduction

(e)

Interpretation: The structure corresponding to 3ethyl1,1dimethylcyclohexane 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.

Answer to Problem 4.40P

The structure corresponding to 3ethyl1,1dimethylcyclohexane is shown as,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.40P , additional homework tip  9

Explanation of Solution

The given IUPAC name is 3ethyl1,1dimethylcyclohexane. The given name is 3ethyl1,1dimethylcyclohexane. The word root used in this is hex. It means structure contains six carbon atoms. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. Therefore, the name suggests that two methyl substituents are attached to the first carbon atom and one ethyl substituent is attached to third carbon atom.

Thus, the correct structure of 3ethyl1,1dimethylcyclohexane is shown below.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.40P , additional homework tip  10

Figure 5

Conclusion

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

Expert Solution
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Interpretation Introduction

(f)

Interpretation: The structure corresponding to 4butyl1,1diethylcyclooctane 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.

Answer to Problem 4.40P

The structure corresponding to 4butyl1,1diethylcyclooctane is shown as,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.40P , additional homework tip  11

Explanation of Solution

The given IUPAC name is 4butyl1,1diethylcyclooctane. The given name is 4butyl1,1diethylcyclooctane. The word root used in this is oct. It means structure contains eight carbon atoms. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. Therefore, the name suggests that two diethyl substituents are attached to the first carbon atom and one butyl substituent is attached to fourth carbon atom.

Thus, the correct structure of 4butyl1,1diethylcyclooctane is shown below.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.40P , additional homework tip  12

Figure 6

Conclusion

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

Expert Solution
Check Mark
Interpretation Introduction

(g)

Interpretation: The structure corresponding to 6isopropyl2,3dimethylnonane 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.

Answer to Problem 4.40P

The structure corresponding to 6isopropyl2,3dimethylnonane is shown as,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.40P , additional homework tip  13

Explanation of Solution

The given IUPAC name is 6isopropyl2,3dimethylnonane. The given name is 6isopropyl2,3dimethylnonane. The word root used in this is non. It means that the structure contains nine carbon atoms. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. Therefore, the name suggests that one methyl substituents are attached to the second and third carbon atom and one isopropyl substituent is attached to the sixth carbon atom.

Thus, the correct structure of 6isopropyl2,3dimethylnonane is shown below.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.40P , additional homework tip  14

Figure 7

Conclusion

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

Expert Solution
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Interpretation Introduction

(h)

Interpretation: The structure corresponding to 2,2,6,6,7pentamethyloctane 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.

Answer to Problem 4.40P

The structure corresponding to 2,2,6,6,7pentamethyloctane is shown as,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.40P , additional homework tip  15

Explanation of Solution

The given IUPAC name is 2,2,6,6,7pentamethyloctane. The given name is 2,2,6,6,7pentamethyloctane. The word root used in this is oct. It means that the structure contains eight carbon atoms. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. Therefore, the name suggests that two methyl substituents are attached to the second and sixth carbon atom and one methyl substituent is attached to the seventh carbon atom.

Thus, the correct structure of 2,2,6,6,7pentamethyloctane is shown below.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.40P , additional homework tip  16

Figure 8

Conclusion

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

Expert Solution
Check Mark
Interpretation Introduction

(i)

Interpretation: The structure corresponding to cis1ethyl3methylcyclopentane is to be stated.

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:

4. First identify the word root for the given compound.

5. The suffix used in the compound like –ene.

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

Answer to Problem 4.40P

The structure corresponding to cis1ethyl3methylcyclopentane is shown as,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.40P , additional homework tip  17

Explanation of Solution

The given IUPAC name is cis1ethyl3methylcyclopentane.

Rules for writing structural formula from IUPAC are

7. First identify the word root for the given compound.

8. The suffix used in the compound like –ene.

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

The given name is cis1ethyl3methylcyclopentane. The word root used in this is pent. It means that the structure contains five carbon atoms. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. Therefore, the name suggests that one ethyl substituents is attached to the first carbon atom and one methyl substituent is attached to the third carbon atom.

Thus, the correct structure of cis1ethyl3methylcyclopentane is shown below.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.40P , additional homework tip  18

Figure 9

Conclusion

The structure corresponding to the given name is shown in Figure 9.

Expert Solution
Check Mark
Interpretation Introduction

(j)

Interpretation: The structure corresponding to trans1tertbutyl4ethylcyclohexane is to be stated.

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:

10. First identify the word root for the given compound.

11. The suffix used in the compound like –ene.

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

Answer to Problem 4.40P

The structure corresponding to trans1tertbutyl4ethylcyclohexane is shown as,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.40P , additional homework tip  19

Explanation of Solution

The given IUPAC name is trans1tertbutyl4ethylcyclohexane.

Rules for writing structural formula from IUPAC are

13. First identify the word root for the given compound.

14. The suffix used in the compound like –ene.

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

The given name is trans1tertbutyl4ethylcyclohexane. The word root used in this is hex. It means that the structure contains six carbon atoms. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. Therefore, the name suggests that one tertiary butyl substituents is attached to the first carbon atom and one ethyl substituent is attached to the fourth carbon atom of cyclohexane.

Thus, the correct structure of trans1tertbutyl4ethylcyclohexane is shown below.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.40P , additional homework tip  20

Figure 10

Conclusion

The structure corresponding to the given name is shown in Figure 10.

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Chapter 4 Solutions

ORGANIC CHEMISTRY

Ch. 4 - Give the IUPAC name for each compound.Ch. 4 - Give the structure corresponding to each IUPAC...Ch. 4 - Arrange the following compounds in order of...Ch. 4 - Problem 4.14 Draw the staggered and eclipsed...Ch. 4 - Prob. 4.15PCh. 4 - Prob. 4.16PCh. 4 - Problem 4.17 a. Draw the three staggered and...Ch. 4 - Problem 4.18 Rank the following conformations in...Ch. 4 - Problem 4.19 Consider rotation around the...Ch. 4 - Calculate the destabilization present in each...Ch. 4 - Problem 4.21 Classify the ring carbons as up or...Ch. 4 - Problem 4.22 Using the cyclohexane with the C’s...Ch. 4 - Draw a second chair conformation for each...Ch. 4 - Problem 4.24 Draw both conformations for and...Ch. 4 - Problem 4.25 Draw the structure for each compound...Ch. 4 - For cis-1, 3-diethylcyclobutane, draw a a...Ch. 4 - Prob. 4.27PCh. 4 - Problem 4.28 Consider . Draw structures f or the...Ch. 4 - Problem 4.29 Draw a chair conformation of...Ch. 4 - Prob. 4.30PCh. 4 - Draw the products of each combustion reaction.Ch. 4 - Explain why beeswax is insoluble in H2O, slightly...Ch. 4 - Prob. 4.33PCh. 4 - Name each alkane using the ball-and-stick model,...Ch. 4 - Consider the substituted cyclohexane shown in the...Ch. 4 - Prob. 4.36PCh. 4 - Prob. 4.37PCh. 4 - 4.38 Give the IUPAC name for each compound. a. c....Ch. 4 - 4.39 Give the structure and IUPAC name for each of...Ch. 4 - 4.40 Draw the structure corresponding to each...Ch. 4 - Prob. 4.41PCh. 4 - 4.42 Give the IUPAC name for each compound. a....Ch. 4 - Prob. 4.43PCh. 4 - Prob. 4.44PCh. 4 - 4.45 Which conformation in each pair is higher in...Ch. 4 - 4.46 Considering rotation around the bond...Ch. 4 - Prob. 4.47PCh. 4 - 4.48 (a) Using Newman projections, draw all...Ch. 4 - 4.49 Label the sites of torsional and steric...Ch. 4 - 4.50 Calculate the barrier to rotation for each...Ch. 4 - 4.51 The eclipsed conformation of is less...Ch. 4 - (a) Draw the anti and gauche conformations for...Ch. 4 - For each compound drawn below: a.Label each OH,Br...Ch. 4 - Draw the two possible chair conformations for...Ch. 4 - For each compound drawn below: a. Draw...Ch. 4 - 4.56 Convert each of the following structures into...Ch. 4 - Prob. 4.57PCh. 4 - Prob. 4.58PCh. 4 - 4.59 Classify each pair of compounds as...Ch. 4 - Classify each pair of compounds as constitutional...Ch. 4 - Prob. 4.61PCh. 4 - 4.62 Draw the three constitutional isomers having...Ch. 4 - Prob. 4.63PCh. 4 - 4.64 Draw the products of combustion of each...Ch. 4 - 4.65 Hydrocarbons like benzene are metabolized in...Ch. 4 - Prob. 4.66PCh. 4 - Prob. 4.67PCh. 4 - Cyclopropane and cyclobutane have similar strain...Ch. 4 - Prob. 4.69PCh. 4 - Haloethanes (CH3CH2X,X=Cl,Br,I) have similar...Ch. 4 - Prob. 4.71PCh. 4 - Prob. 4.72PCh. 4 - Consider the tricyclic structure B (a) Label each...Ch. 4 - Read Appendix B on naming branched alkyl...Ch. 4 - Read Appendix B on naming bicyclic compounds. Then...
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