Chapter 10, Problem 10.39P

Interpretation Introduction

(a)

Interpretation: The structure corresponding to the given $\left(E\right)-4-\text{ethylhept}-3-\text{ene}$ 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.

The use of prefix $E$ and $Z$ depends upon the location of the higher priority groups. When two higher priority groups are present on the opposite side then it is an $E$ isomer, whereas when two higher priority groups are present on the same side then it is a $Z$ isomer. The priority order depends upon the atomic number of the elements.

Answer to Problem 10.39P

The structure corresponding to $\left(E\right)-4-\text{ethylhept}-3-\text{ene}$ is shown in Figure 1.

Explanation of Solution

The given IUPAC name is $\left(E\right)-4-\text{ethylhept}-3-\text{ene}$.

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 use of prefix $E$ and $Z$ depends upon the location of the higher priority groups. When two higher priority groups are present on the opposite side then it is an $E$ isomer, whereas when two higher priority groups are present on the same side then it is a $Z$ isomer.

The given name is $\left(E\right)-4-\text{ethylhept}-3-\text{ene}$. 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 ethyl substituents is attached to the fourth carbon atom. The double bond is present between third and fourth carbon atom. In the given IPUAC name, the prefix used is $E$.

Thus, the correct structure of $\left(E\right)-4-\text{ethylhept}-3-\text{ene}$ is shown below.

Figure 1

Conclusion

The structure corresponding to $\left(E\right)-4-\text{ethylhept}-3-\text{ene}$ is rightfully stated.

Interpretation Introduction

(b)

Interpretation: The structure corresponding to the given $3,3-\text{dimethylcyclopentene}$ 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 10.39P

The structure corresponding to $3,3-\text{dimethylcyclopentene}$ is shown in Figure 2.

Explanation of Solution

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 $3,3-\text{dimethylcyclopentene}$. The word root used in this is pent. It means structure contains five carbon atoms in a cyclic ring. 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 third carbon atom. The double bond is present between first and sedcond carbon atom.

Thus, the correct structure of $3,3-\text{dimethylcyclopentene}$ is shown below.

Figure 2

Conclusion

The structure corresponding to $3,3-\text{dimethylcyclopentene}$ is rightfully stated.

Interpretation Introduction

(c)

Interpretation: The structure corresponding to $4-\text{vinylcyclopentene}$ 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 10.39P

The structure corresponding to $4-\text{vinylcyclopentene}$ is shown in Figure 3.

Explanation of Solution

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 $4-\text{vinylcyclopentene}$. The word root used in this is pent. It means structure contains five carbon atoms in a cyclic ring. 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 vinyl substituents is attached to the fourth carbon atom. The double bond is present between first and second carbon atom.

Thus, the correct structure of $4-\text{vinylcyclopentene}$ is shown below.

Figure 3

Conclusion

The structure corresponding to $4-\text{vinylcyclopentene}$ is rightfully stated.

Interpretation Introduction

(d)

Interpretation: The structure corresponding to $\left(Z\right)-3-\text{isopropylhept}-2-\text{ene}$ 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.

The use of prefix $E$ and $Z$ depends upon the location of the higher priority groups. When two higher priority groups are present on the opposite side then it is an $E$ isomer, whereas when two higher priority groups are present on the same side then it is a $Z$ isomer. The priority order depends upon the atomic number of the elements.

Answer to Problem 10.39P

The structure corresponding to $\left(Z\right)-3-\text{isopropylhept}-2-\text{ene}$ is shown in Figure 4.

Explanation of Solution

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 use of prefix $E$ and $Z$ depends upon the location of the higher priority groups. When two higher priority groups are present on the opposite side then it is an $E$ isomer, whereas when two higher priority groups are present on the same side then it is a $Z$ isomer. The priority order depends upon the atomic number of the elements.

The given name is $\left(Z\right)-3-\text{isopropylhept}-2-\text{ene}$. 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 isopropyl substituent is attached to the third carbon atom. The double bond is present between second and third carbon atom. In the given IPUAC name, the prefix used is $Z$.

Thus, the correct structure of $\left(Z\right)-3-\text{isopropylhept}-2-\text{ene}$ is shown below.

Figure 4

Conclusion

The structure corresponding to $\left(Z\right)-3-\text{isopropylhept}-2-\text{ene}$ is rightfully stated.

Interpretation Introduction

(e)

Interpretation: The structure corresponding to $cis-3,4-\text{dimethylcyclopentene}$ 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 10.39P

The structure corresponding to $cis-3,4-\text{dimethylcyclopentene}$ is shown in Figure 5.

Explanation of Solution

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 $cis-3,4-\text{dimethylcyclopentene}$. The word root used in this is pent. It means structure contains five carbon atoms in a cyclic ring. 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 is attached to the third and fourth carbon atom. The double bond is present between first and second carbon atom. The prefix cis indicates that the two methyl groups are present on same side. They can be represented either in wedge or dashed bonds.

Thus, the two correct structure of $cis-3,4-\text{dimethylcyclopentene}$ is shown below.

Figure 5

Conclusion

The structure corresponding to $cis-3,4-\text{dimethylcyclopentene}$ is rightfully stated.

Interpretation Introduction

(f)

Interpretation: The structure corresponding to $1-\text{isopropyl}-4-\text{propylcyclohexene}$ 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 10.39P

The structure corresponding to $1-\text{isopropyl}-4-\text{propylcyclohexene}$ is shown in Figure 6.

Explanation of Solution

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 $1-\text{isopropyl}-4-\text{propylcyclohexene}$. The word root used in this is hex. It means structure contains six carbon atoms in a cyclic ring. 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 first carbon atom and one propyl substituents is attached to the fourth carbon atom The double bond is present between first and second carbon atom.

Thus, the correct structure of $1-\text{isopropyl}-4-\text{propylcyclohexene}$ is shown below.

Figure 6

Conclusion

The structure corresponding to $1-\text{isopropyl}-4-\text{propylcyclohexene}$ is rightfully stated.

Interpretation Introduction

(g)

Interpretation: The structure corresponding to $3,4-\text{dimethylcyclohex}-2-\text{enol}$ 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 10.39P

The structure corresponding to $3,4-\text{dimethylcyclohex}-2-\text{enol}$ is shown in Figure 7.

Explanation of Solution

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 $3,4-\text{dimethylcyclohex}-2-\text{enol}$. The word root used in this is hex. It means structure contains hex carbon atoms in a cyclic ring. 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 is attached to the third and fourth carbon atom. The double bond is present between second and third carbon atom. Another functional group present in the given name is alcohol $\left(-\text{OH}\right)$.

Thus, the correct structure of $3,4-\text{dimethylcyclohex}-2-\text{enol}$ is shown below.

Figure 7

Conclusion

The structure corresponding to $3,4-\text{dimethylcyclohex}-2-\text{enol}$ is rightfully stated.

Interpretation Introduction

(h)

Interpretation: The structure corresponding to $3,5-\text{diethylcyclohex}-\text{5}-\text{en}-3-\text{ol}$ 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 10.39P

The structure corresponding to $3,5-\text{diethylhex}-\text{5}-\text{en}-3-\text{ol}$ is shown in Figure 8.

Explanation of Solution

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 $3,5-\text{diethylhex}-\text{5}-\text{en}-3-\text{ol}$. The word root used in this is hex. It means structure contains six carbon atoms in a cyclic ring. 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 third and fifth carbon atom. The double bond is present between fifth and sixth carbon atom. Another functional group present in the given name is alcohol $\left(-\text{OH}\right)$.

Thus, the correct structure of $3,5-\text{diethylhex}-\text{5}-\text{en}-3-\text{ol}$ is shown below.

Figure 8

Conclusion

The structure corresponding to $3,5-\text{diethylhex}-\text{5}-\text{en}-3-\text{ol}$ is rightfully stated.