Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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**Radical Halogenation: Stepwise Mechanism**

This section explains the complete mechanism (initiation, propagation, and termination) using arrow-pushing for the radical halogenation of an alkane.

**Chemical Reaction:**

Starting Materials:
- An alkane (depicted with a hydrogen atom attached to a carbon)
- Chlorine molecule (Cl₂)

Reaction Conditions:
- Under the influence of light (hν), which initiates the reaction.

Products:
- Alkane with chlorine substituted for hydrogen
- Hydrogen chloride (HCl)

**Mechanism Steps:**

1. **Initiation:**
   - Light (hν) causes the homolytic cleavage of the Cl₂ molecule, forming two chlorine radicals.

2. **Propagation:**
   - The chlorine radical abstracts a hydrogen from the alkane, forming HCl and a carbon radical on the alkane.
   - The carbon radical then reacts with another Cl₂ molecule, forming the chlorinated alkane and another Cl radical. This Cl radical can continue the chain process.

3. **Termination:**
   - Radicals combine with each other in various ways to terminate the chain reaction:
     - Two Cl radicals form Cl₂.
     - A Cl radical and an alkane radical form chloroalkane.
     - Two alkane radicals form a new C-C bond.

This mechanism highlights the free radical halogenation process, which is crucial for synthetic applications in organic chemistry.
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Transcribed Image Text:**Radical Halogenation: Stepwise Mechanism** This section explains the complete mechanism (initiation, propagation, and termination) using arrow-pushing for the radical halogenation of an alkane. **Chemical Reaction:** Starting Materials: - An alkane (depicted with a hydrogen atom attached to a carbon) - Chlorine molecule (Cl₂) Reaction Conditions: - Under the influence of light (hν), which initiates the reaction. Products: - Alkane with chlorine substituted for hydrogen - Hydrogen chloride (HCl) **Mechanism Steps:** 1. **Initiation:** - Light (hν) causes the homolytic cleavage of the Cl₂ molecule, forming two chlorine radicals. 2. **Propagation:** - The chlorine radical abstracts a hydrogen from the alkane, forming HCl and a carbon radical on the alkane. - The carbon radical then reacts with another Cl₂ molecule, forming the chlorinated alkane and another Cl radical. This Cl radical can continue the chain process. 3. **Termination:** - Radicals combine with each other in various ways to terminate the chain reaction: - Two Cl radicals form Cl₂. - A Cl radical and an alkane radical form chloroalkane. - Two alkane radicals form a new C-C bond. This mechanism highlights the free radical halogenation process, which is crucial for synthetic applications in organic chemistry.
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