SH HS cat. H₂SO4) S. S

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

Write a mechanism for the reaction below 

The image depicts a chemical reaction involving the formation of a thioacetal from a ketone. Here is the transcription and explanation:

**Chemical Reaction:**

Starting Material:
- The starting material is acetophenone, characterized by a benzene ring attached to a carbonyl group (C=O).

Reagents:
- The reaction involves ethanedithiol (HS-CH2-CH2-SH) as the reagent.
- The reaction is catalyzed by sulfuric acid (H2SO4), as indicated by the notation "cat. H2SO4".

Product:
- The product is a thioacetal, where the carbonyl group is transformed into a cyclic sulfide linkage (a dithiolane ring) with two sulfur atoms.

**Reaction Description:**
- The reaction involves the conversion of the carbonyl group in acetophenone into a cyclic thioacetal utilizing ethanedithiol.
- This transformation is catalyzed by an acid, facilitating the removal of water and formation of the cyclic structure with the sulfur atoms.
  
**Diagram/Reaction Scheme:**
- The diagram shows acetophenone on the left side, the reagent and catalyst details above the arrow, and the resulting thioacetal on the right side.
  
This type of reaction is commonly used in organic chemistry to protect carbonyl groups during multi-step synthesis processes.
Transcribed Image Text:The image depicts a chemical reaction involving the formation of a thioacetal from a ketone. Here is the transcription and explanation: **Chemical Reaction:** Starting Material: - The starting material is acetophenone, characterized by a benzene ring attached to a carbonyl group (C=O). Reagents: - The reaction involves ethanedithiol (HS-CH2-CH2-SH) as the reagent. - The reaction is catalyzed by sulfuric acid (H2SO4), as indicated by the notation "cat. H2SO4". Product: - The product is a thioacetal, where the carbonyl group is transformed into a cyclic sulfide linkage (a dithiolane ring) with two sulfur atoms. **Reaction Description:** - The reaction involves the conversion of the carbonyl group in acetophenone into a cyclic thioacetal utilizing ethanedithiol. - This transformation is catalyzed by an acid, facilitating the removal of water and formation of the cyclic structure with the sulfur atoms. **Diagram/Reaction Scheme:** - The diagram shows acetophenone on the left side, the reagent and catalyst details above the arrow, and the resulting thioacetal on the right side. This type of reaction is commonly used in organic chemistry to protect carbonyl groups during multi-step synthesis processes.
Expert Solution
steps

Step by step

Solved in 3 steps with 1 images

Blurred answer
Knowledge Booster
Types of Bonds
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