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:**Nucleophilic Substitution Reactions Analysis**
This exercise involves analyzing and drawing the products of nucleophilic substitution reactions. The reactions presented involve the substitution of bromine (Br) with a cyanide ion (CN⁻) in different organic compounds.
1. **Reaction Details**
a. **Reaction a:**
- **Starting Material:** A six-membered cyclohexane ring substituted with a tert-butyl group ((CH₃)₃C) and a bromine atom at the 1-position.
- **Reagent Used:** Cyanide ion (CN⁻) in acetone.
- **Mechanism:** The cyanide ion acts as a nucleophile, attacking the carbon atom bonded to the bromine, resulting in the removal of the bromine as bromide ion (Br⁻) and the formation of a nitrile group (C≡N) attached to the cyclohexane ring.
b. **Reaction b:**
- **Starting Material:** A six-membered cyclohexane ring with a tert-butyl group ((CH₃)₃C) and a bromine atom at the 2-position.
- **Reagent Used:** Cyanide ion (CN⁻) in acetone.
- **Mechanism:** Similar to reaction a, the cyanide ion acts as a nucleophile, displacing the bromine atom, and forming a new bond between the carbon of the cyclohexane ring and the nitrogen of the cyanide.
Both reactions involve the conversion of a bromoalkane to a nitrile through nucleophilic substitution. The solvent, acetone, is aprotic and facilitates the substitution process by solvating the ions without forming hydrogen bonds.
These reactions demonstrate fundamental principles in organic chemistry, showcasing how nucleophiles interact with alkyl halides to form new functional groups.
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