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Write the complete stepwise mechanism for the following reaction. Show all intermediate structures and all electron flow using arrows. H₂C CH3 HBr H₂C Br CH3

Write the complete stepwise mechanism for the following reaction. Show all intermediate structures and all electron flow using arrows. H₂C CH3 HBr H₂C Br CH3

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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**Stepwise Mechanism for Reaction with HBr** **Problem Statement:** 10. Write the complete stepwise mechanism for the following reaction. Show all intermediate structures and all electron flow using arrows. **Reaction Details:** - **Reactant**: The reactant is a five-membered cyclopentene ring with two methyl groups (CH₃) attached to the second carbon. - **Reagent**: HBr (hydrobromic acid) is used in the reaction. - **Product**: The resulting compound is a cyclopentane ring with a bromine (Br) atom and a methyl group attached to the second carbon, and an additional methyl group on the third carbon. **Reaction Mechanism Steps:** 1. **Protonation of the Alkene:** - The reaction begins with the protonation of the double bond in the cyclopentene ring by HBr. The π electrons of the double bond attack the hydrogen atom of HBr, forming a carbocation at the most stable position. - The formation of the carbocation results in the breaking of the H-Br bond. 2. **Formation of Carbocation Intermediate:** - A secondary carbocation intermediate is formed at the carbon where the double bond was present. The hydrogen is added to one of the carbons that previously formed the double bond. - This carbocation is stabilized by the adjacent methyl groups through hyperconjugation. 3. **Nucleophilic Attack:** - The bromide ion (Br⁻), which is released in the first step, attacks the carbocation. The nucleophilic attack occurs on the carbon with the positive charge. - This results in the formation of the final product, where the bromine is attached to the carbon. **Product Structure:** - The final product is a cyclopentane ring with one bromine (Br) and two methyl (CH₃) groups attached. This mechanism illustrates the electrophilic addition of HBr to an alkene, forming more stable carbocations, followed by nucleophilic attack by the bromide ion. **Note:** It is important to use curved arrows to show the movement of electrons during the reaction steps clearly.
Transcribed Image Text:**Stepwise Mechanism for Reaction with HBr** **Problem Statement:** 10. Write the complete stepwise mechanism for the following reaction. Show all intermediate structures and all electron flow using arrows. **Reaction Details:** - **Reactant**: The reactant is a five-membered cyclopentene ring with two methyl groups (CH₃) attached to the second carbon. - **Reagent**: HBr (hydrobromic acid) is used in the reaction. - **Product**: The resulting compound is a cyclopentane ring with a bromine (Br) atom and a methyl group attached to the second carbon, and an additional methyl group on the third carbon. **Reaction Mechanism Steps:** 1. **Protonation of the Alkene:** - The reaction begins with the protonation of the double bond in the cyclopentene ring by HBr. The π electrons of the double bond attack the hydrogen atom of HBr, forming a carbocation at the most stable position. - The formation of the carbocation results in the breaking of the H-Br bond. 2. **Formation of Carbocation Intermediate:** - A secondary carbocation intermediate is formed at the carbon where the double bond was present. The hydrogen is added to one of the carbons that previously formed the double bond. - This carbocation is stabilized by the adjacent methyl groups through hyperconjugation. 3. **Nucleophilic Attack:** - The bromide ion (Br⁻), which is released in the first step, attacks the carbocation. The nucleophilic attack occurs on the carbon with the positive charge. - This results in the formation of the final product, where the bromine is attached to the carbon. **Product Structure:** - The final product is a cyclopentane ring with one bromine (Br) and two methyl (CH₃) groups attached. This mechanism illustrates the electrophilic addition of HBr to an alkene, forming more stable carbocations, followed by nucleophilic attack by the bromide ion. **Note:** It is important to use curved arrows to show the movement of electrons during the reaction steps clearly.
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Alkene gives an electrophilic addition reaction with hydrogen halide to form an alkyl halide.

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