Draw the major organic product(s) in the sketch pad below.

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

Draw the major organic product(s) in the sketch pad below.

 
**Reaction Description:**

In this chemical reaction, a racemic mixture is presented, composed of two enantiomers of 2-bromo-3-methylbutane. The structures of the enantiomers are shown as follows:

1. The first enantiomer has the bromine (Br) atom in a wedge (indicating it is coming out of the plane) at the second carbon, and the hydrogen (H) atom in a dashed line (indicating it is going into the plane).
2. The second enantiomer has the bromine (Br) atom in a dashed line at the second carbon and the hydrogen (H) atom in a wedge.

Both structures have a methyl (CH₃) group and an ethyl chain, making these compounds structural isomers with stereochemistry at the chiral carbon (second carbon in the chain).

The racemic mixture is treated with sodium hydrosulfide (Na⁺ -SH) in dimethylformamide (DMF) as the solvent. This setup is indicative of a nucleophilic substitution reaction, where the bromine atoms are likely to be replaced by thiolate (-SH) groups, resulting in the formation of new compounds through the reaction pathway. The presence of a racemate indicates that both enantiomers will react, potentially leading to a formation of products that may include a mix of stereoisomers depending on the reaction conditions and mechanism pathway such as SN1 or SN2.
Transcribed Image Text:**Reaction Description:** In this chemical reaction, a racemic mixture is presented, composed of two enantiomers of 2-bromo-3-methylbutane. The structures of the enantiomers are shown as follows: 1. The first enantiomer has the bromine (Br) atom in a wedge (indicating it is coming out of the plane) at the second carbon, and the hydrogen (H) atom in a dashed line (indicating it is going into the plane). 2. The second enantiomer has the bromine (Br) atom in a dashed line at the second carbon and the hydrogen (H) atom in a wedge. Both structures have a methyl (CH₃) group and an ethyl chain, making these compounds structural isomers with stereochemistry at the chiral carbon (second carbon in the chain). The racemic mixture is treated with sodium hydrosulfide (Na⁺ -SH) in dimethylformamide (DMF) as the solvent. This setup is indicative of a nucleophilic substitution reaction, where the bromine atoms are likely to be replaced by thiolate (-SH) groups, resulting in the formation of new compounds through the reaction pathway. The presence of a racemate indicates that both enantiomers will react, potentially leading to a formation of products that may include a mix of stereoisomers depending on the reaction conditions and mechanism pathway such as SN1 or SN2.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 1 images

Blurred answer
Knowledge Booster
Basics in Organic Reaction Mechanisms
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