Chapter 24, Problem 24.19P

Interpretation Introduction

(a)

Interpretation:

Whether the given diol can be produced from an alkene using either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$ is to be determined, and the alkene that can be used to produce it is to be drawn.

Concept introduction:

The alkene, on reaction with ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$, undergoes syn addition and gives $\text{cis-1, 2-diol}$. Thus the $\text{1, 2-}$ diol, which is able to attain cis confirmation, can be prepared through syn addition using either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$. The carbons having $\text{OH}$ groups must have $\text{C=C}$ bond in the alkene.

Answer to Problem 24.19P

The given diol is $\text{cis-1, 2-diol}$; thus can be produced from an alkene using either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$, and the structure of that alkene is

Explanation of Solution

The given diol is

The given diol is $\text{cis-1, 2-diol}$ as both hydroxyl groups are on the same side of the ring; thus it can be produced from an alkene using either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$. The alkene that can be used to produce this diol is identified by replacing the hydroxyl groups and placing the double bond between those carbons. Therefore, the structure of the alkene is

Conclusion

It is determined that the diol can be produced using reagents, either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$, by identifying the diol is $\text{cis-1, 2-diol}$, and the structure of the alkene is drawn by placing the double bond between the carbons having $\text{OH}$ groups.

Interpretation Introduction

(b)

Interpretation:

Whether the given diol can be produced from an alkene using either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$ is to be determined, and the alkene that can be used to produce it is to be drawn.

Concept introduction:

The alkene, on reaction with ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$, undergoes syn addition and gives $\text{cis-1, 2-diol}$. Thus the $\text{1, 2-}$ diol, which is able to attain cis confirmation, can be prepared through syn addition using either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$. The carbons having $\text{OH}$ groups must have $\text{C=C}$ bond in the alkene.

Answer to Problem 24.19P

The given diol is not a $\text{cis-1, 2-diol}$; thus it cannot be produced from an alkene using either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$.

Explanation of Solution

The given diol is

The given diol is not a $\text{cis-1, 2-diol}$ as the hydroxyl groups are on the opposite sides of the ring; thus it cannot be produced from an alkene using either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$.

Conclusion

It is determined that the diol cannot be produced using reagents either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$ by identifying that the diol is not $\text{cis-1, 2-diol}$.

Interpretation Introduction

(c)

Interpretation:

Whether the given diol can be produced from an alkene using either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$ is to be determined, and the alkene that can be used to produce it is to be drawn.

Concept introduction:

The alkene, on reaction with ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$, undergoes syn addition and gives $\text{cis-1, 2-diol}$. Thus the $\text{1, 2-}$ diol, which is able to attain cis confirmation, can be prepared through syn addition using either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$. The carbons having $\text{OH}$ groups must have $\text{C=C}$ bond in the alkene.

Answer to Problem 24.19P

The given diol is not a $\text{cis-1, 2-diol}$; thus it cannot be produced from an alkene using either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$.

Explanation of Solution

The given diol is

The given diol is not a $\text{cis-1, 2-diol}$ as the hydroxyl groups are at $\text{1, 3}$ positions; thus it cannot be produced from an alkene using either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$.

Conclusion

It is determined that the diol cannot be produced using reagents either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$ by identifying that the diol is not $\text{cis-1, 2-diol}$.

Interpretation Introduction

(d)

Interpretation:

Whether the given diol can be produced from an alkene using either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$ is to be determined, and the alkene that can be used to produce it is to be drawn.

Concept introduction:

The alkene, on reaction with ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$, undergoes syn addition and gives $\text{cis-1, 2-diol}$. Thus the $\text{1, 2-}$ diol, which is able to attain cis confirmation, can be prepared through syn addition using either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$. The carbons having $\text{OH}$ groups must have $\text{C=C}$ bond in the alkene.

Answer to Problem 24.19P

The given diol is $\text{cis-1, 2-diol}$; thus it can be produced from an alkene using either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$, and the structure of that alkene is

Explanation of Solution

The given diol is

The given diol is $\text{cis-1, 2-diol}$ as both hydroxyl groups are on the same side of the ring; thus it can be produced from an alkene using either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$. The alkene that can be used to produce this diol is identified by replacing the hydroxyl groups and placing the double bond between those carbons. Therefore, the structure of the alkene is

Conclusion

It is determined that the diol can be produced using reagents either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$ by identifying that the diol is $\text{cis-1, 2-diol}$, and the structure of the alkene is drawn by placing the double bond between the carbons having $\text{OH}$ groups.

Interpretation Introduction

(e)

Interpretation:

Whether the given diol can be produced from an alkene using either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$ is to be determined, and the alkene that can be used to produce it is to be drawn.

Concept introduction:

The alkene, on reaction with ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$, undergoes syn addition and gives $\text{cis-1, 2-diol}$. Thus the $\text{1, 2-}$ diol, which is able to attain cis confirmation, can be prepared through syn addition using either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$. The carbons having $\text{OH}$ groups must have $\text{C=C}$ bond in the alkene.

Answer to Problem 24.19P

The given diol is $\text{1, 2-diol}$ and is able to attain cis conformation through single bond rotation; thus it can be produced from an alkene using either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$, and the structure of that alkene is

Explanation of Solution

The given diol is

The given diol is $\text{trans-1, 2-diol}$ as both hydroxyl groups are on opposite sides of the ring, but it can attain the cis confirmation by single bond rotation. Thus, it can be produced from an alkene using either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$.

The alkene that can be used to produce this diol is identified by replacing the hydroxyl groups and placing the double bond between those carbons. Therefore, the structure of the alkene is

Conclusion

It is determined that the diol can be produced using reagents either ${\text{OsO}}_{\text{4}}$ or ${\text{KMnO}}_{\text{4}}$ by identifying that the diol can attain $\text{cis-1, 2-diol}$ confirmation, and the structure of alkene is drawn by placing the double bond between the carbons having $\text{OH}$ groups.