Chapter 4, Problem 4.47AP

Interpretation Introduction

(a)

Interpretation:

The $E,Z$ configuration is to be assigned to the given structure.

Concept introduction:

Alkenes are the unsaturated class of organic compounds which have a double bond in their structure. The general formula of alkene is written as ${\text{C}}_{\text{n}}{\text{H}}_{\text{2n}}$. The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of the organic compound is correctly interpreted from the name. They give rise to geometrical and stereoisomers, $cis-trans$ or $E-Z$ configuration.

Answer to Problem 4.47AP

The configuration assigned to the given structure is $E$ configuration.

Explanation of Solution

The $E-Z$ configuration is dependent on the atomic number of the atoms attached to the double bond. If the higher priority atoms are present on the same side of the double bond. Then it is assigned as $Z$ configuration and if the higher priority atoms are present on the opposite side of the double bond. Then it is assigned as $E$ configuration. The structure of given alkene is written as shown below.

Figure 1

In this case, bromide ion gets priority over chloride ion and iodide ion gets priority over chloride ion. The structure with higher priority order is written as shown below.

Figure 2

The higher priority groups are present on opposite sides of the double bond. As a result, $E$ configuration is assigned to the given structure.

Conclusion

The configuration of the given structure is $E$.

Interpretation Introduction

(b)

Interpretation:

The $E,Z$ configuration is to be assigned to the given structure.

Concept introduction:

Alkenes are the unsaturated class of organic compounds which have a double bond in their structure. The general formula of alkene is written as ${\text{C}}_{\text{n}}{\text{H}}_{\text{2n}}$. The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of the organic compound is correctly interpreted from the name. They give rise to geometrical and stereoisomers, $cis-trans$ or $E-Z$ configuration.

Answer to Problem 4.47AP

The configuration assigned to the given structure is $Z$ configuration.

Explanation of Solution

The $E-Z$ configuration is dependent on the atomic number of the atoms attached to the double bond. If the higher priority atoms are present on the same side of the double bond, then it is assigned as $Z$ configuration. If the higher priority atoms are present on the opposite side of the double bond, then it is assigned as $E$ configuration. The given structure is written as shown below.

Figure 3

In this case, the atomic mass of deuterium is higher than hydrogen so deuterium gets higher priority over hydrogen. Similarly one ${\text{CH}}_{\text{3}}$ and one ${\text{CD}}_{\text{3}}$ group is present. As already stated the atomic mass of deuterium is higher than hydrogen so ${\text{CD}}_{\text{3}}$ gets higher priority over ${\text{CH}}_{\text{3}}$. The structure with priority number is written a shown below.

Figure 4

The higher priority atoms are present on the same side of the double bond. As a result, $Z$ configuration is assigned to the given structure.

Conclusion

The configuration of the given structure is $Z$.

Interpretation Introduction

(c)

Interpretation:

The $E,Z$ configuration is to be assigned for the given structure.

Concept introduction:

Alkenes are the unsaturated class of organic compounds which have a double bond in their structure. The general formula of alkene is written as ${\text{C}}_{\text{n}}{\text{H}}_{\text{2n}}$. The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of the organic compound is correctly interpreted from the name. They give rise to geometrical and stereoisomers, $cis-trans$ or $E-Z$ configuration.

Answer to Problem 4.47AP

The configuration assigned to the given structure is $E$ configuration.

Explanation of Solution

The $E-Z$ configuration is dependent on the atomic number of the atoms attached to the double bond. If the higher priority atoms are present on the same side of the double bond, then it is assigned as $Z$ configuration . If the higher priority atoms are present on the opposite side of the double bond, then it is assigned as $E$ configuration. The given structure is shown below.

Figure 5

In this case, right side of double bond contains ${\text{CH}}_{\text{3}}$ group and $\text{H}$ atom where carbon gets higher priority over hydrogen. The left side of the double bond contains a carbon atoms cyclic ring whose priority order is identified on the basis of higher priority order atoms attached to its carbon atom which is marked as shown below.

Figure 6

One carbon atom is attached to three carbon atoms and other attached to two carbon atoms. Therefore, the carbon atom which is attached to three carbon atoms gets higher priority. As a result, higher priority atoms are present on opposite sides of the double bond. The structure is assigned $E$ configuration.

Conclusion

The configuration of the given structure is $E$.

Interpretation Introduction

(d)

Interpretation:

The $E,Z$ configuration is to be assigned to the given structure.

Concept introduction:

Alkenes are the unsaturated class of organic compounds which have a double bond in their structure. The general formula of alkene is written as ${\text{C}}_{\text{n}}{\text{H}}_{\text{2n}}$. The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of the organic compound is correctly interpreted from the name. They give rise to geometrical and stereoisomers, $cis-trans$ or $E-Z$ configuration.

Answer to Problem 4.47AP

The configuration assigned to the given structure is $E$ configuration.

Explanation of Solution

The $E-Z$ configuration is dependent on the atomic number of the atoms attached to the double bond. If the higher priority atoms are present on the same side of the double bond, then it is assigned as $Z$ configuration. If the higher priority atoms are present on the opposite side of the double bond, then it is assigned as $E$ configuration. The given structure is shown below.

Figure 7

In this case, left and right side of the double bond contains a carbon atoms cyclic ring whose priority order is identified on the basis of higher priority order atoms attached to its carbon atom which is marked as shown below.

Figure 8

On both sides, One carbon atom is attached to three carbon atoms and other attached to two carbon atoms. Therefore, the carbon atom which is attached to three carbon atoms gets higher priority. Along with double bond get higher priority over the single bond. As a result, higher priority atoms are present on opposite sides of the double bond. The structure is assigned $E$ configuration.

Conclusion

The configuration of the given structure is $E$.