Homework Help is Here – Start Your Trial Now!
Science
Chemistry
In a series of seven steps, (S)-malic acid is converted to the bromoepoxide shown on the right in 50% overall yield. This synthesis is enantioselective-of the stereoisomers pos- sible for the bromoepoxide, only one is formed. OH COOH A (CgH1405) C (C,H1804) НООС (S)-Malic acid D →E F (C,H,OBr2) Br A bromoepoxide 3. LIAIH4, then H,O 4. TSCI, pyridine 5. NaBr, DMSO Steps/reagents: 1. CH,CH,OH, H+ 6. Н.О, СH,COOН 7. KOH 2. H+ In thinking about the chemistry of these steps, you will want to review the use of dihydropyran as an -OH protecting group (Section 16.7D) and the use of the p-toluenesulfonyl chloride to convert the -OH, a poor leaving group, into a tosylate, a good leaving group non

In a series of seven steps, (S)-malic acid is converted to the bromoepoxide shown on the right in 50% overall yield. This synthesis is enantioselective-of the stereoisomers pos- sible for the bromoepoxide, only one is formed. OH COOH A (CgH1405) C (C,H1804) НООС (S)-Malic acid D →E F (C,H,OBr2) Br A bromoepoxide 3. LIAIH4, then H,O 4. TSCI, pyridine 5. NaBr, DMSO Steps/reagents: 1. CH,CH,OH, H+ 6. Н.О, СH,COOН 7. KOH 2. H+ In thinking about the chemistry of these steps, you will want to review the use of dihydropyran as an -OH protecting group (Section 16.7D) and the use of the p-toluenesulfonyl chloride to convert the -OH, a poor leaving group, into a tosylate, a good leaving group non

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
See similar textbooks
icon
Related questions
Question

What is the configuration of the chiral center in the bromoepoxide? How do you account for the stereoselectivity of this seven-step conversion?

In a series of seven steps, (S)-malic acid is converted to the bromoepoxide shown on the right in 50% overall yield. This synthesis is enantioselective-of the stereoisomers pos- sible for the bromoepoxide, only one is formed. OH COOH A (CgH1405) C (C,H1804) НООС (S)-Malic acid D →E F (C,H,OBr2) Br A bromoepoxide 3. LIAIH4, then H,O 4. TSCI, pyridine 5. NaBr, DMSO Steps/reagents: 1. CH,CH,OH, H+ 6. Н.О, СH,COOН 7. KOH 2. H+ In thinking about the chemistry of these steps, you will want to review the use of dihydropyran as an -OH protecting group (Section 16.7D) and the use of the p-toluenesulfonyl chloride to convert the -OH, a poor leaving group, into a tosylate, a good leaving group non
Transcribed Image Text:In a series of seven steps, (S)-malic acid is converted to the bromoepoxide shown on the right in 50% overall yield. This synthesis is enantioselective-of the stereoisomers pos- sible for the bromoepoxide, only one is formed. OH COOH A (CgH1405) C (C,H1804) НООС (S)-Malic acid D →E F (C,H,OBr2) Br A bromoepoxide 3. LIAIH4, then H,O 4. TSCI, pyridine 5. NaBr, DMSO Steps/reagents: 1. CH,CH,OH, H+ 6. Н.О, СH,COOН 7. KOH 2. H+ In thinking about the chemistry of these steps, you will want to review the use of dihydropyran as an -OH protecting group (Section 16.7D) and the use of the p-toluenesulfonyl chloride to convert the -OH, a poor leaving group, into a tosylate, a good leaving group non
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 3 steps with 1 images

SEE SOLUTIONCheck out a sample Q&A here
Blurred answer
Knowledge Booster
Selection Rules for Pericyclic Reactions
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
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY
SEE MORE TEXTBOOKS