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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Transcribed Image Text:**Title: Analyzing the Reaction of 2-Methyl-2-butene with HBr**
**Objective:**
To understand and predict the product(s) formed when 2-methyl-2-butene reacts with HBr.
**Reaction Details:**
- **Starting Material:**
- Structure: 2-Methyl-2-butene
- Description: This is an unsaturated hydrocarbon (alkene) featuring a double bond between the second and third carbon atoms.
- **Reagent:**
- Hydrogen Bromide (HBr)
**Expected Reaction:**
When 2-methyl-2-butene is treated with HBr, a hydrohalogenation reaction occurs. This type of reaction involves the addition of hydrogen (H) and a halogen (Br) across the double bond.
**Mechanism Overview:**
1. **Protonation of the Double Bond:**
- The double bond is protonated by HBr, leading to the formation of a carbocation intermediate. Due to Markovnikov's rule, the proton attaches to the less substituted carbon, resulting in a more stable carbocation.
2. **Carbocation Stability:**
- In this reaction, the most stable carbocation is the tertiary carbocation resulting from the protonation at the less substituted end of the double bond.
3. **Nucleophilic Attack:**
- The bromide ion (Br-) then attacks the carbocation, leading to the formation of the final product.
**Final Product:**
- The major product of this reaction is 2-bromo-2-methylbutane, where the bromine atom is added to the carbon atom that was part of the original double bond, in accordance with Markovnikov's rule.
**Conclusion:**
This reaction is a classic example of electrophilic addition involving alkenes and illustrates the application of Markovnikov's rule, which predicts the regiochemistry of the addition of hydrogen halides to unsymmetrical alkenes.
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