Introductory Chemistry: A Foundation
9th Edition
ISBN:9781337399425
Author:Steven S. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Donald J. DeCoste
Chapter20: Organic Chemistry
Section: Chapter Questions
Problem 4ALQ: How many different possible “tetramethylbenzenes” exist? Provide structural formulas and names for...
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
Transcribed Image Text:### Question 2: Reaction Mechanisms
Draw the mechanism for each of the following transformations:
#### a) Cyclohexene Reaction
- **Reactants and Reagents:** Cyclohexene reacts with HBr.
- **Product:** Bromo-cyclohexane, where a bromine atom is added across the double bond, resulting in a bromo-substituent on the cyclohexane ring.
**Diagram Explanation:**
- The transformation involves the addition of hydrobromic acid (HBr) to cyclohexene.
- The double bond undergoes an electrophilic addition reaction, where the hydrogen from HBr adds to one carbon of the double bond, and the bromide ion adds to the adjacent carbon, forming a bromo-substituted cyclohexane.
#### b) 2-Methyl-2-butene Reaction
- **Reactants and Reagents:** 2-Methyl-2-butene reacts with HCl.
- **Product:** 2-Chloro-2-methylbutane, where a chlorine atom is added to the more substituted carbon of the former double bond.
**Diagram Explanation:**
- This is a classic Markovnikov addition reaction where HCl adds across the double bond.
- The hydrogen atom bonds to the less substituted carbon, while the chlorine atom bonds to the more substituted carbon, generating a tertiary alkyl chloride.
#### c) 2-Methyl-1-butene Reaction
- **Reactants and Reagents:** 2-Methyl-1-butene reacts with HCl.
- **Product:** 2-Chloro-2-methylbutane, where a chlorine atom adds to the more substituted carbon of the double bond.
**Diagram Explanation:**
- Similar to the previous reaction, HCl adds across the double bond in a Markovnikov fashion.
- The chlorine atom attaches to the carbon with more alkyl groups, leading to a chlorinated alkane with enhanced stability at the more substituted site.
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