1 eq HI -78°C coldkinctb

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
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since the temperaure is colder, theless stable product is formed. How do I know which is the less stable product?

**Reaction Scheme Explanation**

This diagram outlines the kinetic reaction of a methylcyclohexene derivative with hydrogen iodide (HI) at low temperature (-78°C). The reaction is described as "cold - kinetic" to emphasize the temperature condition and kinetic control.

**Diagram Details:**

1. **Reactant:** The starting material is a methylcyclohexene derivative depicted on the left.

2. **Reagent:** It reacts with one equivalent of hydrogen iodide (HI).

3. **Temperature Condition:** The reaction occurs at -78°C, denoting it is under kinetic control, which typically favors the faster-forming product.

4. **Major Product Formation:** The middle section shows the addition of the iodine (I) atom to the least substituted carbon of the double bond, as indicated by the attack of iodine, forming the kinetic product.

5. **Mechanism Illustration:**
   - The left side of the mechanism shows the intermediate with the iodine attached and the double bond shifted.
   - An orange wavy line and arrow depict the reaction pathway leading to the kinetic product.

6. **Resonance Structures:**
   - Two possible carbocation intermediates are shown. 
   - The left one shows the iodine anion attacking the more stable secondary (2°) carbocation.
   - A green arrow indicates the attack of iodide (I-) on the carbocation. 

This reaction highlights how low temperature and kinetic control can direct the formation of products in electrophilic addition reactions.
Transcribed Image Text:**Reaction Scheme Explanation** This diagram outlines the kinetic reaction of a methylcyclohexene derivative with hydrogen iodide (HI) at low temperature (-78°C). The reaction is described as "cold - kinetic" to emphasize the temperature condition and kinetic control. **Diagram Details:** 1. **Reactant:** The starting material is a methylcyclohexene derivative depicted on the left. 2. **Reagent:** It reacts with one equivalent of hydrogen iodide (HI). 3. **Temperature Condition:** The reaction occurs at -78°C, denoting it is under kinetic control, which typically favors the faster-forming product. 4. **Major Product Formation:** The middle section shows the addition of the iodine (I) atom to the least substituted carbon of the double bond, as indicated by the attack of iodine, forming the kinetic product. 5. **Mechanism Illustration:** - The left side of the mechanism shows the intermediate with the iodine attached and the double bond shifted. - An orange wavy line and arrow depict the reaction pathway leading to the kinetic product. 6. **Resonance Structures:** - Two possible carbocation intermediates are shown. - The left one shows the iodine anion attacking the more stable secondary (2°) carbocation. - A green arrow indicates the attack of iodide (I-) on the carbocation. This reaction highlights how low temperature and kinetic control can direct the formation of products in electrophilic addition reactions.
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