Designate the absolute configuration of major product of this reaction?

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...
icon
Related questions
icon
Concept explainers
Question
### Designation of Absolute Configuration in a Chemical Reaction

**Problem 13:**
Designate the absolute configuration of the major product of this reaction:

**Reaction Details:**
- The starting material is represented with the chiral center having an (R) absolute configuration.
- The structure of the starting material includes a hydrogen (H) atom, a bromine (Br) atom, and an ethyl group, with the configuration around the chiral center depicted using wedge-and-dash bonds.
- The chemical reagent used in the reaction is sodium methoxide (CH₃ONa).

**Diagram Explanation:**
The starting material has a chiral center marked (R), with the following groups attached:
- Bromine (Br) on a wedge bond (indicating it is coming out of the plane towards the observer).
- Hydrogen (H) on a dash bond (indicating it is going behind the plane away from the observer).
- An ethyl group is also attached but not specifically depicted in terms of spatial orientation in the image.

The reaction arrow indicates that the compound is treated with sodium methoxide (CH₃ONa), a common nucleophile in organic chemistry.

**Task:**
Determine the absolute configuration of the major product after the reaction.

### Analysis and Solution:

When sodium methoxide reacts with the given compound, a nucleophilic substitution reaction occurs. Sodium methoxide will typically attack the carbon atom bonded to bromine, leading to the departure of the bromine atom and the formation of a new bond with the methoxide ion (CH₃O⁻).

**Steps to determine the configuration:**
1. Recognize the type of reaction (likely SN2) which involves inversion of configuration at the chiral center.
2. Apply the Cahn-Ingold-Prelog priority rules to assign the configuration of the product.

By recognizing that the configuration at the chiral center inverts during an SN2 reaction, the absolute configuration of the product will switch from (R) to (S).

### Conclusion:
The absolute configuration of the major product of the given reaction, where a chiral center with initial (R) configuration undergoes nucleophilic substitution with sodium methoxide, is (S).

These details and step-by-step analysis provide a clear understanding of how to designate the absolute configuration of the reaction's major product.
Transcribed Image Text:### Designation of Absolute Configuration in a Chemical Reaction **Problem 13:** Designate the absolute configuration of the major product of this reaction: **Reaction Details:** - The starting material is represented with the chiral center having an (R) absolute configuration. - The structure of the starting material includes a hydrogen (H) atom, a bromine (Br) atom, and an ethyl group, with the configuration around the chiral center depicted using wedge-and-dash bonds. - The chemical reagent used in the reaction is sodium methoxide (CH₃ONa). **Diagram Explanation:** The starting material has a chiral center marked (R), with the following groups attached: - Bromine (Br) on a wedge bond (indicating it is coming out of the plane towards the observer). - Hydrogen (H) on a dash bond (indicating it is going behind the plane away from the observer). - An ethyl group is also attached but not specifically depicted in terms of spatial orientation in the image. The reaction arrow indicates that the compound is treated with sodium methoxide (CH₃ONa), a common nucleophile in organic chemistry. **Task:** Determine the absolute configuration of the major product after the reaction. ### Analysis and Solution: When sodium methoxide reacts with the given compound, a nucleophilic substitution reaction occurs. Sodium methoxide will typically attack the carbon atom bonded to bromine, leading to the departure of the bromine atom and the formation of a new bond with the methoxide ion (CH₃O⁻). **Steps to determine the configuration:** 1. Recognize the type of reaction (likely SN2) which involves inversion of configuration at the chiral center. 2. Apply the Cahn-Ingold-Prelog priority rules to assign the configuration of the product. By recognizing that the configuration at the chiral center inverts during an SN2 reaction, the absolute configuration of the product will switch from (R) to (S). ### Conclusion: The absolute configuration of the major product of the given reaction, where a chiral center with initial (R) configuration undergoes nucleophilic substitution with sodium methoxide, is (S). These details and step-by-step analysis provide a clear understanding of how to designate the absolute configuration of the reaction's major product.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 3 steps with 1 images

Blurred answer
Knowledge Booster
Reactive Intermediates
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