3. Predict the major product and a mechanism for the following reaction xs HCI

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
Question
**Question 3**

**Problem Statement:**

Predict the major product and a mechanism for the following reaction:

**Chemical Reaction:**

- Reactants: A cyclohexyl group attached to a propynyl group (alkyne).
- Reagents: Excess hydrochloric acid (HCl).

**Explanation:**

The given compound is an alkyne attached to a cyclohexyl ring. In the presence of excess HCl, hydrohalogenation occurs. This reaction typically proceeds via a Markovnikov addition, where the hydrogen atom adds to the carbon with the most hydrogen atoms (the terminal carbon of the alkyne), leading to the formation of a dichlorinated alkane.

**Mechanism:**

1. **First Addition of HCl:**
   - The alkyne reacts with HCl, where the hydrogen ion (H⁺) adds to the terminal carbon, and the chloride ion (Cl⁻) adds to the more substituted carbon. This forms a vinyl chloride.

2. **Second Addition of HCl:**
   - The formed vinyl chloride reacts with another equivalent of HCl.
   - The hydrogen adds to the carbon with the Cl from the first addition, and another chloride ion adds to the neighboring carbon, forming a geminal dichloride.

**Major Product:**

The major product is a geminal dichloride, where both chlorine atoms are added to the carbons of what was initially an alkyne.
Transcribed Image Text:**Question 3** **Problem Statement:** Predict the major product and a mechanism for the following reaction: **Chemical Reaction:** - Reactants: A cyclohexyl group attached to a propynyl group (alkyne). - Reagents: Excess hydrochloric acid (HCl). **Explanation:** The given compound is an alkyne attached to a cyclohexyl ring. In the presence of excess HCl, hydrohalogenation occurs. This reaction typically proceeds via a Markovnikov addition, where the hydrogen atom adds to the carbon with the most hydrogen atoms (the terminal carbon of the alkyne), leading to the formation of a dichlorinated alkane. **Mechanism:** 1. **First Addition of HCl:** - The alkyne reacts with HCl, where the hydrogen ion (H⁺) adds to the terminal carbon, and the chloride ion (Cl⁻) adds to the more substituted carbon. This forms a vinyl chloride. 2. **Second Addition of HCl:** - The formed vinyl chloride reacts with another equivalent of HCl. - The hydrogen adds to the carbon with the Cl from the first addition, and another chloride ion adds to the neighboring carbon, forming a geminal dichloride. **Major Product:** The major product is a geminal dichloride, where both chlorine atoms are added to the carbons of what was initially an alkyne.
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
Selection Rules for Pericyclic Reactions
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