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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where does water come from

Transcribed Image Text:### Mechanism of Cyclohexene Reaction with Chlorine in Water
This diagram illustrates the reaction of cyclohexene with chlorine in the presence of water, leading to the formation of a halohydrin.
**Step-by-Step Explanation:**
1. **Initial Reaction:**
- Cyclohexene reacts with chlorine (\( Cl_2 \)).
- A cyclic chloronium ion is formed, represented by a three-membered ring with a positive charge (\( Cl^+ \)) on one carbon.
2. **Nucleophilic Attack:**
- A chloride ion (\( Cl^- \)) and water (\( H_2O \)) are produced after the formation of the chloronium ion.
- Water acts as a nucleophile, attacking the more substituted carbon in the chloronium ion.
3. **Opening of the Chloronium Ion:**
- The attack by water opens the three-membered ring, leading to the formation of a haloalcohol intermediate.
- This intermediate features a chloride and a water molecule attached to adjacent carbons.
4. **Proton Transfer:**
- A proton (\( H^+ \)) is transferred, resulting in the formation of the final halohydrin product, where the hydroxyl group (OH) and chloride (Cl) are on adjacent carbons.
- Additionally, hydronium ion (\( H_3O^+ \)) is formed as a byproduct.
### Key Features:
- **Chlorination Mechanism:** Involves the formation of a positively charged chloronium ion.
- **Water as Nucleophile:** Water participates in the reaction by opening the chloronium ion.
- **Halohydrin Formation:** The reaction concludes with the formation of a halohydrin, a molecule containing an alcohol and halogen on adjacent carbons.
This reaction is an example of an addition reaction in organic chemistry, specifically involving alkenes and halogens with water, demonstrating how addition of polar molecules can proceed through cyclic intermediates.
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