Br NaSCH3. THE

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 product of an SN2 reaction shown below. Use wedge and dash bonds to indicate stereochemistry where appropriate. Indicate inorganic byproducts.

### SN2 Reaction Example

**Starting Material:**
- **Structure:** The starting material is a linear alkane with a terminal bromine (Br) atom attached.
- **Reagents:** Sodium thiomethoxide (NaSCH₃) and tetrahydrofuran (THF).

**Reaction Type:**
- The reaction depicted is an SN2 nucleophilic substitution. 

**Mechanism Overview:**
- In this SN2 reaction, the nucleophile (NaSCH₃) attacks the electrophilic carbon atom that has the bromine (Br) attached.
- This attack results in the inversion of configuration at the carbon atom.
- The bromine is displaced, leaving the carbon chain and the thiomethoxide group bonded.

**Expected Outcome:**
- The product of this reaction will be an alkane with the SCH₃ group replacing the bromine atom.

**Instruction:**
- Draw the SN2 product where the Br atom is substituted with the SCH₃ group on the original carbon structure.

This exercise illustrates the fundamental nature of SN2 reactions, specifically the direct replacement of one substituent with another in a concerted mechanism, leading to inversion of stereochemistry at the reaction site.
Transcribed Image Text:### SN2 Reaction Example **Starting Material:** - **Structure:** The starting material is a linear alkane with a terminal bromine (Br) atom attached. - **Reagents:** Sodium thiomethoxide (NaSCH₃) and tetrahydrofuran (THF). **Reaction Type:** - The reaction depicted is an SN2 nucleophilic substitution. **Mechanism Overview:** - In this SN2 reaction, the nucleophile (NaSCH₃) attacks the electrophilic carbon atom that has the bromine (Br) attached. - This attack results in the inversion of configuration at the carbon atom. - The bromine is displaced, leaving the carbon chain and the thiomethoxide group bonded. **Expected Outcome:** - The product of this reaction will be an alkane with the SCH₃ group replacing the bromine atom. **Instruction:** - Draw the SN2 product where the Br atom is substituted with the SCH₃ group on the original carbon structure. This exercise illustrates the fundamental nature of SN2 reactions, specifically the direct replacement of one substituent with another in a concerted mechanism, leading to inversion of stereochemistry at the reaction site.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Nomenclature of Organic 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.
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