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...
Related questions
Question

Transcribed Image Text:**Question 5:**
**Provide a mechanism for the following transformation:**
- The reactant is a tertiary alcohol, 2-methylpropan-2-ol.
- It undergoes a transformation in the presence of sulfuric acid (\( \text{H}_2\text{SO}_4 \)).
**Reaction Details:**
- **Reactant:** The molecule has a hydroxyl group (\( -\text{OH} \)) attached to the central carbon of a three-carbon chain with a methyl group attached to the second carbon.
- **Reagent:** \( \text{H}_2\text{SO}_4 \), which acts as a strong acid, indicating that the mechanism likely involves protonation.
- **Product:** The product is an alkene, specifically 2-methylpropene, formed by the elimination of water.
**Mechanism Explanation:**
1. **Protonation Step:** The hydroxyl group in the alcohol is protonated by the sulfuric acid. This step converts the \( -\text{OH} \) group into water (\( \text{H}_2\text{O} \)), a better leaving group.
2. **Formation of Carbocation:** Once the \( \text{H}_2\text{O} \) group leaves, a carbocation is formed at the tertiary carbon center.
3. **Deprotonation and Alkene Formation:** A hydrogen ion is abstracted from one of the neighboring carbon atoms, leading to the formation of a double bond between the carbons, resulting in the alkene.
This is an example of an acid-catalyzed dehydration reaction, which proceeds via an E1 mechanism typical in such transformations involving secondary or tertiary alcohols.
Expert Solution

This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
This is a popular solution!
Trending now
This is a popular solution!
Step by step
Solved in 2 steps with 1 images

Knowledge Booster
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
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning

Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education

Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning

Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning

Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education

Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning

Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education

Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning

Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY