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...
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![**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.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F2e409500-00e3-48e9-ac9f-d003a0ee1067%2F32d64ad7-dce5-401f-8ab1-0006da8787f6%2Fineijzp_processed.jpeg&w=3840&q=75)
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.
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