For the compounds shown below, identify the two beta hydrogens and give the major Hofmann elimination product. а) CH2CH3 CH3 ОН `CH3 H3C b) O N(CH3)3 OH ¯
For the compounds shown below, identify the two beta hydrogens and give the major Hofmann elimination product. а) CH2CH3 CH3 ОН `CH3 H3C b) O N(CH3)3 OH ¯
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:** Identifying Beta Hydrogens and Predicting Hofmann Elimination Products
**Objective:** Learn to identify beta hydrogens and predict the major product in Hofmann elimination reactions.
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**Instructions:**
For the compounds shown below, identify the two beta hydrogens and give the major Hofmann elimination product.
**Compound a:**
- Structure: Cyclohexane ring with an ethyl group (CH₂CH₃) attached. It also contains a quaternary ammonium group where nitrogen (N⁺) is bonded to three methyl groups (CH₃) and the ammonium ion is paired with a hydroxide ion (OH⁻).
- Reaction: The compound undergoes a Hofmann elimination reaction when heated (indicated by the delta symbol, Δ).
**Compound b:**
- Structure: A carbon chain with branching:
1. A straight chain with several carbons.
2. A quaternary ammonium group (N⁺) is bonded to three methyl groups (CH₃), paired with a hydroxide ion (OH⁻).
- Reaction: The compound undergoes a Hofmann elimination reaction when heated (indicated by the delta symbol, Δ).
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In Hofmann elimination, the least substituted alkene is typically favored, which means the focus would be on identifying the less hindered beta hydrogens.
**Important Concepts:**
1. **Beta Hydrogen:** In an organic molecule, beta hydrogens are the hydrogens on the carbon adjacent to the carbon bonded to the leaving group (here, the nitrogen atom).
2. **Hofmann Elimination:** A type of elimination reaction where the major product is the least substituted alkene, typically using a strong base at high temperatures.
By analyzing the structures given, determine which beta hydrogens will participate in the reaction and predict the major alkene formed in each case.
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