Chapter 4, Problem 4.40P

Draw the structure corresponding to each IUPAC name.

a. $3-\text{ethyl}-2-\text{methylhexane}$

b. $\sec -\text{butylcyclopentane}$

c. $4-\text{isopropyl}-2,4,5-\text{trimethylundecane}$

d. cyclobutylcycloheptane

e. $3-\text{ethyl}-1,1-\text{dimethylcyclohexane}$

f. $4-\text{butyl}-1,1-\text{diethylcycloocatne}$

g $6-\text{isopropyl}-2,3-\text{dimethylocatne}$

h. $2,2,6,6,7-\text{pentamethylocatne}$

i. $cis-1-\text{ethyl}-3-\text{methylcyclopentane}$

j. $trans-1-tert-\text{butyl}-4-\text{ethylcycloheaxne}$

Interpretation Introduction

(a)

Interpretation: The structure corresponding to $3-\text{ethyl}-2-\text{methylhexane}$ 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 $3-\text{ethyl}-2-\text{methylhexane}$ is shown as,

Explanation of Solution

The given IUPAC name is $3-\text{ethyl}-2-\text{methylhexane}$.

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 $3-\text{ethyl}-2-\text{methylhexane}$. 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 $3-\text{ethyl}-2-\text{methylhexane}$ is shown below.

Figure 1

Conclusion

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

Interpretation Introduction

(b)

Interpretation: The structure corresponding to $\sec -\text{butylcyclopentane}$ 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 $\sec -\text{butylcyclopentane}$ is shown as,

Explanation of Solution

The given IUPAC name is $\sec -\text{butylcyclopentane}$.

The given name is $\sec -\text{butylcyclopentane}$. 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 $\sec -\text{butylcyclopentane}$ is shown below.

Figure 2

Conclusion

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

Interpretation Introduction

(c)

Interpretation: The structure corresponding to $4-\text{isopropyl}-2,4,5-\text{trimethylheptane}$ 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 $4-\text{isopropyl}-2,4,5-\text{trimethylheptane}$ is shown as,

Explanation of Solution

The given IUPAC name is $4-\text{isopropyl}-2,4,5-\text{trimethylheptane}$.

The given name is $4-\text{isopropyl}-2,4,5-\text{trimethylheptane}$. 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 $4-\text{isopropyl}-2,4,5-\text{trimethylheptane}$ is shown below.

Figure 3

Conclusion

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

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,

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.

Figure 4

Conclusion

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

Interpretation Introduction

(e)

Interpretation: The structure corresponding to $3-\text{ethyl}-1,1-\text{dimethylcyclohexane}$ 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 $3-\text{ethyl}-1,1-\text{dimethylcyclohexane}$ is shown as,

Explanation of Solution

The given IUPAC name is $3-\text{ethyl}-1,1-\text{dimethylcyclohexane}$. The given name is $3-\text{ethyl}-1,1-\text{dimethylcyclohexane}$. 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 $3-\text{ethyl}-1,1-\text{dimethylcyclohexane}$ is shown below.

Figure 5

Conclusion

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

Interpretation Introduction

(f)

Interpretation: The structure corresponding to $4-\text{butyl}-1,1-\text{diethylcyclooctane}$ 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 $4-\text{butyl}-1,1-\text{diethylcyclooctane}$ is shown as,

Explanation of Solution

The given IUPAC name is $4-\text{butyl}-1,1-\text{diethylcyclooctane}$. The given name is $4-\text{butyl}-1,1-\text{diethylcyclooctane}$. 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 $4-\text{butyl}-1,1-\text{diethylcyclooctane}$ is shown below.

Figure 6

Conclusion

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

Interpretation Introduction

(g)

Interpretation: The structure corresponding to $6-\text{isopropyl}-2,3-\text{dimethylnonane}$ 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 $6-\text{isopropyl}-2,3-\text{dimethylnonane}$ is shown as,

Explanation of Solution

The given IUPAC name is $6-\text{isopropyl}-2,3-\text{dimethylnonane}$. The given name is $6-\text{isopropyl}-2,3-\text{dimethylnonane}$. 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 $6-\text{isopropyl}-2,3-\text{dimethylnonane}$ is shown below.

Figure 7

Conclusion

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

Interpretation Introduction

(h)

Interpretation: The structure corresponding to $2,2,6,6,7-\text{pentamethyloctane}$ 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 $2,2,6,6,7-\text{pentamethyloctane}$ is shown as,

Explanation of Solution

The given IUPAC name is $2,2,6,6,7-\text{pentamethyloctane}$. The given name is $2,2,6,6,7-\text{pentamethyloctane}$. 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 $2,2,6,6,7-\text{pentamethyloctane}$ is shown below.

Figure 8

Conclusion

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

Interpretation Introduction

(i)

Interpretation: The structure corresponding to $cis-1-\text{ethyl}-3-\text{methylcyclopentane}$ 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 $cis-1-\text{ethyl}-3-\text{methylcyclopentane}$ is shown as,

Explanation of Solution

The given IUPAC name is $cis-1-\text{ethyl}-3-\text{methylcyclopentane}$.

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 $cis-1-\text{ethyl}-3-\text{methylcyclopentane}$. 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 $cis-1-\text{ethyl}-3-\text{methylcyclopentane}$ is shown below.

Figure 9

Conclusion

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

Interpretation Introduction

(j)

Interpretation: The structure corresponding to $trans-1-\text{tert}-\text{butyl}-4-\text{ethylcyclohexane}$ 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 $trans-1-\text{tert}-\text{butyl}-4-\text{ethylcyclohexane}$ is shown as,

Explanation of Solution

The given IUPAC name is $trans-1-\text{tert}-\text{butyl}-4-\text{ethylcyclohexane}$.

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 $trans-1-\text{tert}-\text{butyl}-4-\text{ethylcyclohexane}$. 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 $trans-1-\text{tert}-\text{butyl}-4-\text{ethylcyclohexane}$ is shown below.

Figure 10

Conclusion

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