Organic Chemistry
Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
bartleby

Concept explainers

bartleby

Videos

Textbook Question
Book Icon
Chapter 12, Problem 12.44P

What alkene is needed to synthesize each 1 , 2 -diol using the [ 1 ] OsO 4 followed by NaHSO 3 in H 2 O ;

or [ 2 ] CH 3 CO 3 H followed by OH in H 2 O ?

a. Chapter 12, Problem 12.44P, What alkene is needed to synthesize each 1,2-diol using the [1] OsO4 followed by NaHSO3 in H2O; or , example  1 b. Chapter 12, Problem 12.44P, What alkene is needed to synthesize each 1,2-diol using the [1] OsO4 followed by NaHSO3 in H2O; or , example  2 c. Chapter 12, Problem 12.44P, What alkene is needed to synthesize each 1,2-diol using the [1] OsO4 followed by NaHSO3 in H2O; or , example  3

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: The alkene needed to synthesize the given 1,2-diol using [1] OsO4 followed by NaHSO3+H2O; or [2] CH3CO3H followed by H2O,OH is to be predicted.

Concept introduction: Addition of two hydroxyl groups on double bond to form 1,2-diol is known as dihydroxylation. In presence of OsO4, syn dihydroxylation takes place. In this reaction, two hydroxyl groups are added on the same side of the double bond.

In the presence of peroxide, alkene is oxidized to epoxide. This is known as epoxidation. This is a syn addition. The weak pi bond of alkene and weak OO bond of peroxide are broken and two new CO bonds are formed. Breaking of bonds and formation of bonds takes place in single step. In opening of the epoxide ring the nucleophile attacks from the backside of the CO bond.

Answer to Problem 12.44P

The alkene needed to synthesize the given 1,2-diol using the [1] OsO4 followed by NaHSO3+H2O; or [2] CH3CO3H followed by H2O,OH is shown in Figure 1 and Figure 3.

Explanation of Solution

[1] OsO4 followed by NaHSO3+H2O

In presence of OsO4 followed by hydrolysis with NaHSO3+H2O, 1,2-diol is formed. This is syn dihydroxylation. The required alkene is,

Organic Chemistry, Chapter 12, Problem 12.44P , additional homework tip  1

Figure 1

The corresponding chemical reaction is given below.

Organic Chemistry, Chapter 12, Problem 12.44P , additional homework tip  2

Figure 2

[2] CH3CO3H followed by H2O,OH

In presence of CH3CO3H, alkene is oxidized to epoxide. Epoxidation is followed by ring opening with H2O,OH. This is anti dihydroxylation. The required alkene is,

Organic Chemistry, Chapter 12, Problem 12.44P , additional homework tip  3

Figure 3

The corresponding chemical reaction is given below.

Organic Chemistry, Chapter 12, Problem 12.44P , additional homework tip  4

Figure 4

Conclusion

The alkene needed to synthesize the given 1,2-diol using the [1] OsO4 followed by NaHSO3+H2O; or [2] CH3CO3H followed by H2O,OH is shown in Figure 1 and Figure 3.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The alkene needed to synthesize the given 1,2-diol using the [1] OsO4 followed by NaHSO3+H2O; or [1] CH3CO3H followed by H2O,OH is to be predicted.

Concept introduction: Addition of two hydroxyl groups on double bond to form 1,2-diol is known as dihydroxylation. In presence of OsO4, syn dihydroxylation takes place. In this reaction, two hydroxyl groups are added on the same side of the double bond.

In the presence of peroxide, alkene is oxidized to epoxide. This is known as epoxidation. This is a syn addition. The weak pi bond of alkene and weak OO bond of peroxide are broken and two new CO bonds are formed. Breaking of bonds and formation of bonds takes place in single step. In opening of the epoxide ring the nucleophile attacks from the backside of the CO bond.

Answer to Problem 12.44P

The alkene needed to synthesize the given 1,2-diol using the [1] OsO4 followed by NaHSO3+H2O; or [2] CH3CO3H followed by H2O,OH is shown in Figure 5 and Figure 7.

Explanation of Solution

[1] OsO4 followed by NaHSO3+H2O

In presence of OsO4 followed by hydrolysis with NaHSO3+H2O, 1,2-diol is formed. This is syn dihydroxylation. The required alkene is,

Organic Chemistry, Chapter 12, Problem 12.44P , additional homework tip  5

Figure 5

The chemical reaction is given below.

Organic Chemistry, Chapter 12, Problem 12.44P , additional homework tip  6

Figure 6

[2] CH3CO3H followed by H2O,OH

In presence of CH3CO3H, alkene is oxidized to epoxide. Epoxidation is followed by ring opening with H2O,OH. This is anti dihydroxylation. The required alkene is,

Organic Chemistry, Chapter 12, Problem 12.44P , additional homework tip  7

Figure 7

The chemical reaction is given below.

Organic Chemistry, Chapter 12, Problem 12.44P , additional homework tip  8

Figure 8

Conclusion

The alkene needed to synthesize the given 1,2-diol using the [1] OsO4 followed by NaHSO3+H2O; or [2] CH3CO3H followed by H2O,OH is shown in Figure 5 and Figure 7.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The alkene needed to synthesize the given 1,2-diol using the [1] OsO4 followed by NaHSO3+H2O; or [1] CH3CO3H followed by H2O,OH is to be predicted.

Concept introduction: Addition of two hydroxyl groups on double bond to form 1,2-diol is known as dihydroxylation. In presence of OsO4, syn dihydroxylation takes place. In this reaction two hydroxyl groups are added on the same side of the double bond.

In the presence of peroxide, alkene is oxidized to epoxide. This is known as epoxidation. This is a syn addition. The weak pi bond of alkene and weak OO bond of peroxide are broken and two new CO bonds are formed. Breaking of bonds and formation of bonds takes place in single step. In opening of the epoxide ring the nucleophile attacks from the backside of the CO bond.

Answer to Problem 12.44P

The alkene needed to synthesize the given 1,2-diol using the [1] OsO4 followed by NaHSO3+H2O; or [2] CH3CO3H followed by H2O,OH is shown in Figure 10 and Figure 12.

Explanation of Solution

The given alkene is,

Organic Chemistry, Chapter 12, Problem 12.44P , additional homework tip  9

Figure 9

This is a staggered conformation in which two hydroxyl groups are anti to each other.

[1] OsO4 followed by NaHSO3+H2O

In presence of OsO4 followed by hydrolysis with NaHSO3+H2O, 1,2-diol is formed. This is syn dihydroxylation. The required alkene is,

Organic Chemistry, Chapter 12, Problem 12.44P , additional homework tip  10

Figure 10

The chemical reaction is given below.

Organic Chemistry, Chapter 12, Problem 12.44P , additional homework tip  11

Figure 11

[2] CH3CO3H followed by H2O,OH

In presence of CH3CO3H, alkene is oxidized to epoxide. Epoxidation is followed by ring opening with H2O,OH. This is anti dihydroxylation. The required alkene is,

Organic Chemistry, Chapter 12, Problem 12.44P , additional homework tip  12

Figure 12

The chemical reaction is given below.

Organic Chemistry, Chapter 12, Problem 12.44P , additional homework tip  13

Figure 13

Conclusion

The alkene needed to synthesize the given 1,2-diol using the [1] OsO4 followed by NaHSO3+H2O; or [2] CH3CO3H followed by H2O,OH is shown in Figure 10 and Figure 12.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!
Students have asked these similar questions
Order-disorder phenomenaa) do not have conductive properties.b) are cooperative.c) have few industrial implications.
None
Show work. Don't give Ai and copied solution

Chapter 12 Solutions

Organic Chemistry

Ch. 12 - Problem 12.11 (a) Draw the structure of a compound...Ch. 12 - Prob. 12.12PCh. 12 - Prob. 12.13PCh. 12 - Problem 12.14 Draw the products of each...Ch. 12 - Prob. 12.15PCh. 12 - Problem 12.16 Draw all stereoisomers formed when...Ch. 12 - Prob. 12.17PCh. 12 - Problem 12.18 Draw the products formed when both...Ch. 12 - Problem 12.19 Draw the products formed when each...Ch. 12 - Prob. 12.20PCh. 12 - Prob. 12.21PCh. 12 - Problem 12.22 Draw the products formed when each...Ch. 12 - Prob. 12.23PCh. 12 - Problem 12.24 Draw the organic products in each of...Ch. 12 - Prob. 12.25PCh. 12 - Prob. 12.26PCh. 12 - Problem 12.27 Draw the products of each Sharpless...Ch. 12 - Prob. 12.28PCh. 12 - 12.29 Draw the products formed when A is treated...Ch. 12 - Prob. 12.30PCh. 12 - 12.31 Devise a synthesis of the following compound...Ch. 12 - Prob. 12.32PCh. 12 - Prob. 12.33PCh. 12 - Prob. 12.34PCh. 12 - Prob. 12.35PCh. 12 - Prob. 12.36PCh. 12 - 12.37 Stearidonic acid (C18H28O2) is an...Ch. 12 - Draw the organic products formed when cyclopentene...Ch. 12 - Draw the organic products formed when allylic...Ch. 12 - Draw the organic products formed in each reaction....Ch. 12 - Prob. 12.41PCh. 12 - Prob. 12.42PCh. 12 - Prob. 12.43PCh. 12 - What alkene is needed to synthesize each 1,2-diol...Ch. 12 - Prob. 12.45PCh. 12 - 12.46 (a)What product is formed in Step [1] of the...Ch. 12 - Draw the products formed after Steps 1 and 2 in...Ch. 12 - 12.48 Draw the products formed in each oxidative...Ch. 12 - What alkene or alkyne yields each set of products...Ch. 12 - Prob. 12.50PCh. 12 - Prob. 12.51PCh. 12 - Prob. 12.52PCh. 12 - Prob. 12.53PCh. 12 - 12.54 An unknown compound A of molecular formula ...Ch. 12 - 12.55 DHA is a fatty acid derived from fish oil...Ch. 12 - Prob. 12.56PCh. 12 - 12.57 Draw the product of each asymmetric...Ch. 12 - 12.58 Epoxidation of the following allylic alcohol...Ch. 12 - Prob. 12.59PCh. 12 - 12.60 Identify A in the following reaction...Ch. 12 - Prob. 12.61PCh. 12 - 12.62 It is sometimes necessary to isomerize a cis...Ch. 12 - 12.63 Devise a synthesis of each compound from...Ch. 12 - Prob. 12.64PCh. 12 - Prob. 12.65PCh. 12 - 12.66 Devise a synthesis of each compound from the...Ch. 12 - Prob. 12.67PCh. 12 - Prob. 12.68PCh. 12 - 12.69 Devise a synthesis of each compound from as...Ch. 12 - Prob. 12.70PCh. 12 - Prob. 12.71PCh. 12 - 12.72 Draw a stepwise mechanism for the following...Ch. 12 - Prob. 12.73PCh. 12 - Prob. 12.74PCh. 12 - 12.75 Sharpless epoxidation of allylic alcohol X...
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
  • Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305580350
    Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
    Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
How to Design a Total Synthesis; Author: Chemistry Unleashed;https://www.youtube.com/watch?v=9jRfAJJO7mM;License: Standard YouTube License, CC-BY