Homework Help is Here – Start Your Trial Now!
Science
Chemistry
Determine the mechanistic pathway and product(s) for the reaction. Justify your responses using the four (4) criteria. Be specific with respect to configuration and major/minor product mixtures where appropriate. H3C CH3 Br CH3 H3C ONa DMSO ?

Determine the mechanistic pathway and product(s) for the reaction. Justify your responses using the four (4) criteria. Be specific with respect to configuration and major/minor product mixtures where appropriate. H3C CH3 Br CH3 H3C ONa DMSO ?

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

The Four Criteria referred to in directions are attached 

**Text for Educational Website:** **Title:** Reaction Mechanism and Product Determination **Description:** In this exercise, we aim to determine the mechanistic pathway and product(s) for the given reaction. Analyze and justify your responses using the following four criteria: 1. **Nucleophilicity and Electrophilicity:** Examine the reactivity of the participants based on their nucleophilic or electrophilic nature. 2. **Solvent Effects:** Consider the role of dimethyl sulfoxide (DMSO) as the solvent, which can influence the reaction pathway. 3. **Stereochemistry:** Pay attention to configuration changes resulting from the reaction and the formation of any stereoisomers. 4. **Product Mixture:** Identify and distinguish between major and minor products where applicable. **Reaction Details:** - **Substrate:** 2-bromo-2,3-dimethylbutane - **Reagent:** Sodium acetate (NaOAc) in DMSO **Diagram Explanation:** The starting material is 2-bromo-2,3-dimethylbutane, a tertiary alkyl bromide. It reacts with sodium acetate (NaOAc), which serves as a nucleophile, in the presence of DMSO, a polar aprotic solvent. Your task is to deduce the likely pathway (S_N1, S_N2, E1, or E2) and predict the product(s), considering the mechanisms and stability factors involved. Analyze and discuss the potential pathways, addressing the likelihood of substitution versus elimination, and predict the stereochemistry and configuration of the product(s). Consider both kinetics and thermodynamics to determine which products are major or minor. **Objective:** Your goal is to accurately determine the products and justify your conclusions based on these criteria.
Transcribed Image Text:**Text for Educational Website:** **Title:** Reaction Mechanism and Product Determination **Description:** In this exercise, we aim to determine the mechanistic pathway and product(s) for the given reaction. Analyze and justify your responses using the following four criteria: 1. **Nucleophilicity and Electrophilicity:** Examine the reactivity of the participants based on their nucleophilic or electrophilic nature. 2. **Solvent Effects:** Consider the role of dimethyl sulfoxide (DMSO) as the solvent, which can influence the reaction pathway. 3. **Stereochemistry:** Pay attention to configuration changes resulting from the reaction and the formation of any stereoisomers. 4. **Product Mixture:** Identify and distinguish between major and minor products where applicable. **Reaction Details:** - **Substrate:** 2-bromo-2,3-dimethylbutane - **Reagent:** Sodium acetate (NaOAc) in DMSO **Diagram Explanation:** The starting material is 2-bromo-2,3-dimethylbutane, a tertiary alkyl bromide. It reacts with sodium acetate (NaOAc), which serves as a nucleophile, in the presence of DMSO, a polar aprotic solvent. Your task is to deduce the likely pathway (S_N1, S_N2, E1, or E2) and predict the product(s), considering the mechanisms and stability factors involved. Analyze and discuss the potential pathways, addressing the likelihood of substitution versus elimination, and predict the stereochemistry and configuration of the product(s). Consider both kinetics and thermodynamics to determine which products are major or minor. **Objective:** Your goal is to accurately determine the products and justify your conclusions based on these criteria.
**The Four Criteria** 1. **Leaving Group** - A. Meant to be a check for poor LGs, like OH, C, H, and F = NO RXN - B. Recall that LG-ability tracks with conjugate pKa where poor Brønsted-Lowry bases are the best LGs 2. **Nucleophile- Choosing between Sn and E** - A. Better Lewis than Brønsted-Lowry = Sn - B. Better Brønsted-Lowry than Lewis = E - C. Good/poor at both = does both either quickly or slowly 3. **Electrophile- Choosing between bimolecular and unimolecular molecularity** - A. Sterically unhindered E+ make unstable carbocations = bimolecular - B. Sterically hindered E+ make stable carbocations = unimolecular 4. **Solvent- Most often used to decide secondary E+ and/or kinetics** - A. Nonpolar (LDF) - no effect on anything - B. Polar aprotic (d/d) - encourages bimolecular pathways - C. Polar protic (H-bonds) - encourages unimolecular pathways
Transcribed Image Text:**The Four Criteria** 1. **Leaving Group** - A. Meant to be a check for poor LGs, like OH, C, H, and F = NO RXN - B. Recall that LG-ability tracks with conjugate pKa where poor Brønsted-Lowry bases are the best LGs 2. **Nucleophile- Choosing between Sn and E** - A. Better Lewis than Brønsted-Lowry = Sn - B. Better Brønsted-Lowry than Lewis = E - C. Good/poor at both = does both either quickly or slowly 3. **Electrophile- Choosing between bimolecular and unimolecular molecularity** - A. Sterically unhindered E+ make unstable carbocations = bimolecular - B. Sterically hindered E+ make stable carbocations = unimolecular 4. **Solvent- Most often used to decide secondary E+ and/or kinetics** - A. Nonpolar (LDF) - no effect on anything - B. Polar aprotic (d/d) - encourages bimolecular pathways - C. Polar protic (H-bonds) - encourages unimolecular pathways
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 2 images

SEE SOLUTIONCheck out a sample Q&A here
Blurred answer
Follow-up Questions
Read through expert solutions to related follow-up questions below.
Follow-up Question

-OAc can be used for Sn2 as well 

How would this be incorporated into the answer

 

Solution
Bartleby Expert
SEE SOLUTION
Knowledge Booster
Organopalladium Compounds
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.
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