Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Williamson Ether Synthesis
An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction…
Question

The hydrobrominationof 2-methyl-1-butene could theoretically lead to 2 different alkyl bromides; in practice only one product is formed. Draw the structure of both theoretical products, circle the one that is actually produced, and briefly explain whyonly one product forms.

### Electrophilic Addition of HBr to an Alkene #### Reaction Overview: The image depicts a chemical reaction in which an alkene undergoes an electrophilic addition reaction with hydrogen bromide (HBr) to form a bromoalkane. **Reactants:** - The alkene reagent shown on the left is propene, with the chemical structure CH₃-CH=CH₂. **Reagent:** - The reagent used in the reaction is hydrogen bromide (HBr). **Reaction Arrow:** - An arrow points from the reactants towards the right, indicating the direction of the chemical reaction. #### Reaction Description: In this reaction, hydrogen bromide adds to the double bond of the propene molecule. This process involves the following steps: 1. **Electrophilic Attack:** - The π electrons of the double bond in propene attack the hydrogen atom of HBr, creating a carbocation intermediate and bromide anion (Br⁻). 2. **Formation of Carbocation:** - The more stable carbocation, a secondary carbocation (CH₃-CH⁺-CH₃), is formed as an intermediate. 3. **Nucleophilic Attack:** - The bromide anion (Br⁻) then attacks the carbocation, producing the final product. **Product:** - The final product is 2-bromopropane (CH₃-CHBr-CH₃). The reaction follows Markovnikov's rule, where the hydrogen atom from HBr attaches to the carbon of the double bond that has more hydrogen atoms, resulting in the formation of the more stable carbocation intermediate. #### Application: Understanding this reaction is essential in organic synthesis and helps in grasping the fundamental concepts of electrophilic addition mechanisms and regiospecificity in organic chemistry. This reaction is commonly studied in undergraduate organic chemistry courses.
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Transcribed Image Text:### Electrophilic Addition of HBr to an Alkene #### Reaction Overview: The image depicts a chemical reaction in which an alkene undergoes an electrophilic addition reaction with hydrogen bromide (HBr) to form a bromoalkane. **Reactants:** - The alkene reagent shown on the left is propene, with the chemical structure CH₃-CH=CH₂. **Reagent:** - The reagent used in the reaction is hydrogen bromide (HBr). **Reaction Arrow:** - An arrow points from the reactants towards the right, indicating the direction of the chemical reaction. #### Reaction Description: In this reaction, hydrogen bromide adds to the double bond of the propene molecule. This process involves the following steps: 1. **Electrophilic Attack:** - The π electrons of the double bond in propene attack the hydrogen atom of HBr, creating a carbocation intermediate and bromide anion (Br⁻). 2. **Formation of Carbocation:** - The more stable carbocation, a secondary carbocation (CH₃-CH⁺-CH₃), is formed as an intermediate. 3. **Nucleophilic Attack:** - The bromide anion (Br⁻) then attacks the carbocation, producing the final product. **Product:** - The final product is 2-bromopropane (CH₃-CHBr-CH₃). The reaction follows Markovnikov's rule, where the hydrogen atom from HBr attaches to the carbon of the double bond that has more hydrogen atoms, resulting in the formation of the more stable carbocation intermediate. #### Application: Understanding this reaction is essential in organic synthesis and helps in grasping the fundamental concepts of electrophilic addition mechanisms and regiospecificity in organic chemistry. This reaction is commonly studied in undergraduate organic chemistry courses.
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