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:### Reaction Mechanism Prediction
**Task:** Predict the most likely mechanism for the reaction shown below.
**Reaction Overview:**
A cyclohexane ring with a chlorine substituent (Cl) and two methyl groups (CH₃) in a 1,3-dimethyl arrangement undergoes reaction in the presence of water (H₂O) and heat (Δ).
**Diagram:**
- The starting molecule is a 1-chloro-3,3-dimethyl-cyclohexane.
- The chlorine atom is positioned at the first carbon of the cyclohexane ring.
- Adjacent to the chlorine, there are two methyl groups attached to the third carbon of the ring.
- The reaction conditions are represented by H₂O and the symbol Δ (which represents heat).
**Explanation:**
Given the presence of the chlorine substituent and the reaction conditions (H₂O and heat), the most likely mechanism for this reaction is the nucleophilic substitution reaction, specifically an Sₙ1 mechanism due to the stabilization of the carbocation by the inductive and hyperconjugative effects of the methyl groups.
### Expected Sₙ1 Reaction Steps:
1. **Formation of a Carbocation:** The chlorine leaving group departs, forming a tertiary carbocation (3°), which is stabilized by the adjacent methyl groups.
2. **Nucleophilic Attack:** Water (H₂O) acts as a nucleophile, attacking the carbocation, leading to the formation of a protonated alcohol.
3. **Deprotonation:** The protonated alcohol loses a proton (H⁺), forming the final alcohol product.
**Key Points:**
- **Sₙ1 Mechanism** involves a two-step process: ionization to form a carbocation followed by nucleophilic attack.
- **Stabilization of the Carbocation**: The two methyl groups donate electron density via hyperconjugation, stabilizing the positive charge.
- **Heat** (Δ) provides the necessary energy to overcome the activation barrier for the leaving group to depart.
This Sₙ1 mechanism is favored in the presence of a strong polar solvent like water and the ability to stabilize the intermediate carbocation.
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