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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
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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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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**Title:** Identifying Beta Hydrogens and Predicting Hofmann Elimination Products **Objective:** Learn to identify beta hydrogens and predict the major product in Hofmann elimination reactions. --- **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). --- 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.
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. --- **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). --- 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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