Chapter 4, Problem 4.75P

Read Appendix B on naming bicyclic compounds. Then give IUPAC name for each of the following compounds.

a.

b.

c.

d.

Interpretation Introduction

(a)

Interpretation: The IUPAC name for the given bicyclic compound is to be stated.

Concept introduction: The root name of bicyclic compounds depends upon the number of carbon atoms present in the rings. The naming of bicyclic compounds is done as,

(1) The total number of carbon atoms in the molecule is to be counted. It represents the root name.

(2) The number of carbon atoms between the bridgeheads is to be counted and placed in square brackets in descending order.

(3) The word bicyclo is placed at the beginning of the name.

The general name such compounds is represented as $\text{bicyclo}\left[\text{x}\text{.y}\text{.z}\right]\text{alkane}$.

Answer to Problem 4.75P

The IUPAC name for the given bicyclic compound is $2,3-\text{dimethylbicyclo}\left[\text{3}\text{.1}\text{.1}\right]\text{heptane}$.

Explanation of Solution

The given bicyclic compound is shown below.

Figure 1

The given compound contains seven carbon atoms in the ring which are single bonded to each other. Therefore, the root name is heptane. In this case, there are $3,1$ and $1$ carbon atoms present between the bridgehead which are placed in descending order as $\left[\text{3}\text{.1}\text{.1}\right]$. There are two dimethyl groups present at ${\text{C}}_{\text{2}}$ and ${\text{C}}_3$ positions. Hence, the IUPAC name for the given bicyclic compound is $2,3-\text{dimethylbicyclo}\left[\text{3}\text{.1}\text{.1}\right]\text{heptane}$.

Conclusion

The IUPAC name for the given bicyclic compound is $2,3-\text{dimethylbicyclo}\left[\text{3}\text{.1}\text{.1}\right]\text{heptane}$.

Interpretation Introduction

(b)

Interpretation: The IUPAC name for the given bicyclic compound is to be stated.

Concept introduction: The root name of bicyclic compounds depends upon the number of carbon atoms present in the rings. The naming of bicyclic compounds is done as,

(1) The total number of carbon atoms in the molecule is to be counted. It represents the root name.

(2) The number of carbon atoms between the bridgeheads is to be counted and placed in square brackets in descending order.

(3) The word bicyclo is placed at the beginning of the name.

The general name such compounds is represented as $\text{bicyclo}\left[\text{x}\text{.y}\text{.z}\right]\text{alkane}$.

Answer to Problem 4.75P

The IUPAC name for the given bicyclic compound is $2-\text{ethyl}-7,7-\text{dimethylbicyclo}\left[\text{2}\text{.2}\text{.1}\right]\text{heptane}$.

Explanation of Solution

The given bicyclic compound is shown below.

Figure 2

The given compound contains seven carbon atoms in the ring which are single bonded to each other. Therefore, the root name is heptane. In this case, there are $2,2$ and $1$ carbon atoms present between the bridgehead which are placed in descending order as $\left[\text{2}\text{.2}\text{.1}\right]$. There are two methyl groups present at ${\text{C}}_7$ position and one ethyl group at ${\text{C}}_2$ position. Hence, the IUPAC name for the given bicyclic compound is $2-\text{ethyl}-7,7-\text{dimethylbicyclo}\left[\text{2}\text{.2}\text{.1}\right]\text{heptane}$.

Conclusion

The IUPAC name for the given bicyclic compound is $2-\text{ethyl}-7,7-\text{dimethylbicyclo}\left[\text{2}\text{.2}\text{.1}\right]\text{heptane}$.

Interpretation Introduction

(c)

Interpretation: The IUPAC name for the given bicyclic compound is to be stated.

Concept introduction: The root name of bicyclic compounds depends upon the number of carbon atoms present in the rings. The naming of bicyclic compounds is done as,

(1) The total number of carbon atoms in the molecule is to be counted. It represents the root name.

(2) The number of carbon atoms between the bridgeheads is to be counted and placed in square brackets in descending order.

(3) The word bicyclo is placed at the beginning of the name.

The general name such compounds is represented as $\text{bicyclo}\left[\text{x}\text{.y}\text{.z}\right]\text{alkane}$.

Answer to Problem 4.75P

The IUPAC name for the given bicyclic compound is $1-\text{methyl}-7-\text{propylbicyclo}\left[\text{3}\text{.2}\text{.1}\right]\text{octane}$.

Explanation of Solution

The given bicyclic compound is shown below.

Figure 3

The given compound contains eight carbon atoms in the ring which are single bonded to each other. Therefore, the root name is octane. In this case, there are $3,2$ and $1$ carbon atoms present between the bridgehead which are placed in descending order as $\left[\text{3}\text{.2}\text{.1}\right]$. There is one propyl group present at ${\text{C}}_7$ position and one methyl group at ${\text{C}}_1$ position. Hence, the IUPAC name for the given bicyclic compound is $1-\text{methyl}-7-\text{propylbicyclo}\left[\text{3}\text{.2}\text{.1}\right]\text{octane}$.

Conclusion

The IUPAC name for the given bicyclic compound is $1-\text{methyl}-7-\text{propylbicyclo}\left[\text{3}\text{.2}\text{.1}\right]\text{octane}$.

Interpretation Introduction

(d)

Interpretation: The IUPAC name for the given bicyclic compound is to be stated.

Concept introduction: The root name of bicyclic compounds depends upon the number of carbon atoms present in the rings. The naming of bicyclic compounds is done as,

(1) The total number of carbon atoms in the molecule is to be counted. It represents the root name.

(2) The number of carbon atoms between the bridgeheads is to be counted and placed in square brackets in descending order.

(3) The word bicyclo is placed at the beginning of the name.

The general name such compounds is represented as $\text{bicyclo}\left[\text{x}\text{.y}\text{.z}\right]\text{alkane}$.

Answer to Problem 4.75P

The IUPAC name for the given bicyclic compound is $6-\text{ethyl}-3,3-\text{dimethylbicyclo}\left[\text{3}\text{.2}\text{.0}\right]\text{heptane}$.

Explanation of Solution

The given bicyclic compound is shown below.

Figure 4

The given compound contains seven carbon atoms in the ring which are single bonded to each other. Therefore, the root name is heptane. In this case, there are $3,2$ and $0$ carbon atoms present between the bridgehead which are placed in descending order as $\left[\text{3}\text{.2}\text{.0}\right]$. There is one ethyl group present at ${\text{C}}_6$ position and two methyl groups at ${\text{C}}_3$ position. Hence, the IUPAC name for the given bicyclic compound is $6-\text{ethyl}-3,3-\text{dimethylbicyclo}\left[\text{3}\text{.2}\text{.0}\right]\text{heptane}$.

Conclusion

The IUPAC name for the given bicyclic compound is $6-\text{ethyl}-3,3-\text{dimethylbicyclo}\left[\text{3}\text{.2}\text{.0}\right]\text{heptane}$.