Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
Question
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Chapter 24, Problem 24.19P
Interpretation Introduction

(a)

Interpretation:

Whether the given diol can be produced from an alkene using either OsO4 or KMnO4 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 OsO4 or KMnO4, undergoes syn addition and gives cis-1, 2-diol. Thus the 1, 2- diol, which is able to attain cis confirmation, can be prepared through syn addition using either OsO4 or KMnO4. The carbons having OH groups must have C=C bond in the alkene.

Expert Solution
Check Mark

Answer to Problem 24.19P

The given diol is cis-1, 2-diol; thus can be produced from an alkene using either OsO4 or KMnO4, and the structure of that alkene is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 24, Problem 24.19P , additional homework tip  1

Explanation of Solution

The given diol is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 24, Problem 24.19P , additional homework tip  2

The given diol is 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 OsO4 or KMnO4. 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

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 24, Problem 24.19P , additional homework tip  3

Conclusion

It is determined that the diol can be produced using reagents, either OsO4 or KMnO4, by identifying the diol is cis-1, 2-diol, and the structure of the alkene is drawn by placing the double bond between the carbons having OH groups.

Interpretation Introduction

(b)

Interpretation:

Whether the given diol can be produced from an alkene using either OsO4 or KMnO4 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 OsO4 or KMnO4, undergoes syn addition and gives cis-1, 2-diol. Thus the 1, 2- diol, which is able to attain cis confirmation, can be prepared through syn addition using either OsO4 or KMnO4. The carbons having OH groups must have C=C bond in the alkene.

Expert Solution
Check Mark

Answer to Problem 24.19P

The given diol is not a cis-1, 2-diol; thus it cannot be produced from an alkene using either OsO4 or KMnO4.

Explanation of Solution

The given diol is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 24, Problem 24.19P , additional homework tip  4

The given diol is not a 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 OsO4 or KMnO4.

Conclusion

It is determined that the diol cannot be produced using reagents either OsO4 or KMnO4 by identifying that the diol is not cis-1, 2-diol.

Interpretation Introduction

(c)

Interpretation:

Whether the given diol can be produced from an alkene using either OsO4 or KMnO4 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 OsO4 or KMnO4, undergoes syn addition and gives cis-1, 2-diol. Thus the 1, 2- diol, which is able to attain cis confirmation, can be prepared through syn addition using either OsO4 or KMnO4. The carbons having OH groups must have C=C bond in the alkene.

Expert Solution
Check Mark

Answer to Problem 24.19P

The given diol is not a cis-1, 2-diol; thus it cannot be produced from an alkene using either OsO4 or KMnO4.

Explanation of Solution

The given diol is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 24, Problem 24.19P , additional homework tip  5

The given diol is not a cis-1, 2-diol as the hydroxyl groups are at 1, 3 positions; thus it cannot be produced from an alkene using either OsO4 or KMnO4.

Conclusion

It is determined that the diol cannot be produced using reagents either OsO4 or KMnO4 by identifying that the diol is not cis-1, 2-diol.

Interpretation Introduction

(d)

Interpretation:

Whether the given diol can be produced from an alkene using either OsO4 or KMnO4 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 OsO4 or KMnO4, undergoes syn addition and gives cis-1, 2-diol. Thus the 1, 2- diol, which is able to attain cis confirmation, can be prepared through syn addition using either OsO4 or KMnO4. The carbons having OH groups must have C=C bond in the alkene.

Expert Solution
Check Mark

Answer to Problem 24.19P

The given diol is cis-1, 2-diol; thus it can be produced from an alkene using either OsO4 or KMnO4, and the structure of that alkene is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 24, Problem 24.19P , additional homework tip  6

Explanation of Solution

The given diol is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 24, Problem 24.19P , additional homework tip  7

The given diol is 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 OsO4 or KMnO4. 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

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 24, Problem 24.19P , additional homework tip  8

Conclusion

It is determined that the diol can be produced using reagents either OsO4 or KMnO4 by identifying that the diol is cis-1, 2-diol, and the structure of the alkene is drawn by placing the double bond between the carbons having OH groups.

Interpretation Introduction

(e)

Interpretation:

Whether the given diol can be produced from an alkene using either OsO4 or KMnO4 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 OsO4 or KMnO4, undergoes syn addition and gives cis-1, 2-diol. Thus the 1, 2- diol, which is able to attain cis confirmation, can be prepared through syn addition using either OsO4 or KMnO4. The carbons having OH groups must have C=C bond in the alkene.

Expert Solution
Check Mark

Answer to Problem 24.19P

The given diol is 1, 2-diol and is able to attain cis conformation through single bond rotation; thus it can be produced from an alkene using either OsO4 or KMnO4, and the structure of that alkene is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 24, Problem 24.19P , additional homework tip  9

Explanation of Solution

The given diol is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 24, Problem 24.19P , additional homework tip  10

The given diol is 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 OsO4 or KMnO4.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 24, Problem 24.19P , additional homework tip  11

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

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 24, Problem 24.19P , additional homework tip  12

Conclusion

It is determined that the diol can be produced using reagents either OsO4 or KMnO4 by identifying that the diol can attain cis-1, 2-diol confirmation, and the structure of alkene is drawn by placing the double bond between the carbons having OH groups.

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Chapter 24 Solutions

Organic Chemistry: Principles and Mechanisms (Second Edition)

Ch. 24 - Prob. 24.11PCh. 24 - Prob. 24.12PCh. 24 - Prob. 24.13PCh. 24 - Prob. 24.14PCh. 24 - Prob. 24.15PCh. 24 - Prob. 24.16PCh. 24 - Prob. 24.17PCh. 24 - Prob. 24.18PCh. 24 - Prob. 24.19PCh. 24 - Prob. 24.20PCh. 24 - Prob. 24.21PCh. 24 - Prob. 24.22PCh. 24 - Prob. 24.23PCh. 24 - Prob. 24.24PCh. 24 - Prob. 24.25PCh. 24 - Prob. 24.26PCh. 24 - Prob. 24.27PCh. 24 - Prob. 24.28PCh. 24 - Prob. 24.29PCh. 24 - Prob. 24.30PCh. 24 - Prob. 24.31PCh. 24 - Prob. 24.32PCh. 24 - Prob. 24.33PCh. 24 - Prob. 24.34PCh. 24 - Prob. 24.35PCh. 24 - Prob. 24.36PCh. 24 - Prob. 24.37PCh. 24 - Prob. 24.38PCh. 24 - Prob. 24.39PCh. 24 - Prob. 24.40PCh. 24 - Prob. 24.41PCh. 24 - Prob. 24.42PCh. 24 - Prob. 24.43PCh. 24 - Prob. 24.44PCh. 24 - Prob. 24.45PCh. 24 - Prob. 24.46PCh. 24 - Prob. 24.47PCh. 24 - Prob. 24.48PCh. 24 - Prob. 24.49PCh. 24 - Prob. 24.50PCh. 24 - Prob. 24.51PCh. 24 - Prob. 24.52PCh. 24 - Prob. 24.53PCh. 24 - Prob. 24.54PCh. 24 - Prob. 24.55PCh. 24 - Prob. 24.56PCh. 24 - Prob. 24.57PCh. 24 - Prob. 24.58PCh. 24 - Prob. 24.59PCh. 24 - Prob. 24.60PCh. 24 - Prob. 24.61PCh. 24 - Prob. 24.62PCh. 24 - Prob. 24.63PCh. 24 - Prob. 24.64PCh. 24 - Prob. 24.65PCh. 24 - Prob. 24.66PCh. 24 - Prob. 24.67PCh. 24 - Prob. 24.68PCh. 24 - Prob. 24.69PCh. 24 - Prob. 24.70PCh. 24 - Prob. 24.71PCh. 24 - Prob. 24.72PCh. 24 - Prob. 24.73PCh. 24 - Prob. 24.74PCh. 24 - Prob. 24.75PCh. 24 - Prob. 24.76PCh. 24 - Prob. 24.77PCh. 24 - Prob. 24.78PCh. 24 - Prob. 24.79PCh. 24 - Prob. 24.80PCh. 24 - Prob. 24.81PCh. 24 - Prob. 24.82PCh. 24 - Prob. 24.83PCh. 24 - Prob. 24.84PCh. 24 - Prob. 24.1YTCh. 24 - Prob. 24.2YTCh. 24 - Prob. 24.3YTCh. 24 - Prob. 24.4YTCh. 24 - Prob. 24.5YTCh. 24 - Prob. 24.6YTCh. 24 - Prob. 24.7YTCh. 24 - Prob. 24.8YTCh. 24 - Prob. 24.9YTCh. 24 - Prob. 24.10YTCh. 24 - Prob. 24.11YTCh. 24 - Prob. 24.12YTCh. 24 - Prob. 24.13YTCh. 24 - Prob. 24.14YTCh. 24 - Prob. 24.15YTCh. 24 - Prob. 24.16YTCh. 24 - Prob. 24.17YT
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