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What are the relevant transition states for this reaction?

What are the relevant transition states for this reaction?

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
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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What are the relevant transition states for this reaction?

The image depicts a chemical reaction involving the dehydrohalogenation of an alkyl chloride. **Reactant:** - The starting compound is a chlorinated cyclopentane derivative, specifically 1-chloro-1-methylcyclopentane. **Reagents and Conditions:** - The reaction involves the use of potassium tert-butoxide (t-BuOK) as a base. - The reaction is performed under heat (denoted by the delta symbol, Δ). - The solvent used is tert-butanol (t-BuOH). **Products:** - The reaction yields two alkenes: 1. The major product is methylenecyclopentane, where a double bond forms between the exocyclic carbon and one of the ring carbons. 2. The minor product is 1-methylcyclopentene, where the double bond forms within the cyclopentane ring at the position opposite the methyl group. This reaction exemplifies an elimination (E2) process where the base abstracts a proton, leading to the formation of a double bond while expelling the chloride as a leaving group. The stability of the resulting alkenes and steric factors influence the major and minor products.
Transcribed Image Text:The image depicts a chemical reaction involving the dehydrohalogenation of an alkyl chloride. **Reactant:** - The starting compound is a chlorinated cyclopentane derivative, specifically 1-chloro-1-methylcyclopentane. **Reagents and Conditions:** - The reaction involves the use of potassium tert-butoxide (t-BuOK) as a base. - The reaction is performed under heat (denoted by the delta symbol, Δ). - The solvent used is tert-butanol (t-BuOH). **Products:** - The reaction yields two alkenes: 1. The major product is methylenecyclopentane, where a double bond forms between the exocyclic carbon and one of the ring carbons. 2. The minor product is 1-methylcyclopentene, where the double bond forms within the cyclopentane ring at the position opposite the methyl group. This reaction exemplifies an elimination (E2) process where the base abstracts a proton, leading to the formation of a double bond while expelling the chloride as a leaving group. The stability of the resulting alkenes and steric factors influence the major and minor products.
Expert Solution
Step 1

This is an elimination reaction. Potassium tertiary butoxide (tBuOK) is a strong and very bulky base. Hence, it will preferably pick up streric repulsion free proton. Here, 3 primary C-H hydrogen and 4 secondary C-H hydrogens are present. As picking up of primary hydrogen involves less steric repulsion, it will give major product formation. 

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