Homework Help is Here – Start Your Trial Now!
Science
Chemistry
2. The following elimination will not give the desired alkene product. Identify the mistake(s) in the proposed reaction and correct it by writing a new reaction. KO'Bu, DMSQ + КОН

2. The following elimination will not give the desired alkene product. Identify the mistake(s) in the proposed reaction and correct it by writing a new reaction. KO'Bu, DMSQ + КОН

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
icon
Concept explainers
Question
100%
**Problem 2: Elimination Reaction Analysis** The diagram showcases an elimination reaction where 2-butanol is treated with potassium tert-butoxide (KOtBu) in dimethyl sulfoxide (DMSO). The reaction aims to produce an alkene. ### Components: - **Reactant:** 2-Butanol (with a hydroxyl group on the secondary carbon) - **Reagents:** KOtBu (potassium tert-butoxide) and DMSO (dimethyl sulfoxide) - **Expected Product:** An alkene with a double bond at a specific location, accompanied by potassium hydroxide (KOH) as a byproduct. ### Issue to Address: The reaction depicted will not result in the desired alkene product. ### Task: - Identify the mistake(s) within the proposed reaction mechanism. - Write a corrected reaction that leads to the proper formation of an alkene. **Explanation:** - **Original Reaction Problem:** The reaction conditions listed (use of KOtBu and DMSO) typically favor dehydrohalogenation or E2 eliminations. However, to form an alkene directly via alcohol starting material, further examination of the conditions and possible intermediates or leaving groups might reveal discrepancies. - **Correction Method:** Ensure the proper conversion of the alcohol functional group into a suitable leaving group before elimination occurs (e.g., conversion to tosylate). Then proceed with E2 via a strong base like KOtBu. This setup may necessitate alternative subject material or conditions to provide the reactive environment needed for eliminating reactions.
Transcribed Image Text:**Problem 2: Elimination Reaction Analysis** The diagram showcases an elimination reaction where 2-butanol is treated with potassium tert-butoxide (KOtBu) in dimethyl sulfoxide (DMSO). The reaction aims to produce an alkene. ### Components: - **Reactant:** 2-Butanol (with a hydroxyl group on the secondary carbon) - **Reagents:** KOtBu (potassium tert-butoxide) and DMSO (dimethyl sulfoxide) - **Expected Product:** An alkene with a double bond at a specific location, accompanied by potassium hydroxide (KOH) as a byproduct. ### Issue to Address: The reaction depicted will not result in the desired alkene product. ### Task: - Identify the mistake(s) within the proposed reaction mechanism. - Write a corrected reaction that leads to the proper formation of an alkene. **Explanation:** - **Original Reaction Problem:** The reaction conditions listed (use of KOtBu and DMSO) typically favor dehydrohalogenation or E2 eliminations. However, to form an alkene directly via alcohol starting material, further examination of the conditions and possible intermediates or leaving groups might reveal discrepancies. - **Correction Method:** Ensure the proper conversion of the alcohol functional group into a suitable leaving group before elimination occurs (e.g., conversion to tosylate). Then proceed with E2 via a strong base like KOtBu. This setup may necessitate alternative subject material or conditions to provide the reactive environment needed for eliminating reactions.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 1 images

SEE SOLUTIONCheck out a sample Q&A here
Blurred answer
Knowledge Booster
Ethers
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
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