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Identify the major product for the E2 reaction that occurs when the following substrates are treated with a strong base: a) Br af Br as b)

Identify the major product for the E2 reaction that occurs when the following substrates are treated with a strong base: a) Br af Br as b)

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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**E2 Reaction and Major Products:** For an E2 reaction, a strong base is used to deprotonate a substrate, leading to the formation of a double bond by elimination. In the given examples, substrates a) and b) both undergo elimination reactions to form alkenes. **a) Substrate Overview:** - Structure: The substrate contains a bromine (Br) atom bonded to a carbon, which is adjacent to a phenyl (benzene) ring. There is also a tertiary butyl group attached. - Key Features: The bromine atom is on a wedge, indicating its stereochemistry, and the molecule has a chiral center. **b) Substrate Overview:** - Structure: This substrate also includes a bromine (Br) atom bonded to a carbon adjacent to a phenyl ring, with a tertiary butyl group as well. - Key Features: In this structure, the bromine atom is on a dash, representing a different stereochemistry at the chiral center compared to substrate a). **E2 Major Product Explanation:** - In E2 reactions, the base removes a hydrogen from the carbon adjacent to the one bearing the leaving group (bromine in these examples), leading to the formation of a double bond. - For substrate a), when treated with a strong base, the likely major product will have the double bond formed between the carbon atoms adjacent to where the bromine was, favoring the formation of the more stable, highly substituted alkene. - Similarly, substrate b) will form a double bond, again favoring the more substituted alkene, with the configuration depending on the stereochemistry of the starting material. These reactions exemplify regioselectivity and stereoselectivity in E2 reactions, often leading to the most stable (Zaitsev) alkene when multiple products are possible.
Transcribed Image Text:**E2 Reaction and Major Products:** For an E2 reaction, a strong base is used to deprotonate a substrate, leading to the formation of a double bond by elimination. In the given examples, substrates a) and b) both undergo elimination reactions to form alkenes. **a) Substrate Overview:** - Structure: The substrate contains a bromine (Br) atom bonded to a carbon, which is adjacent to a phenyl (benzene) ring. There is also a tertiary butyl group attached. - Key Features: The bromine atom is on a wedge, indicating its stereochemistry, and the molecule has a chiral center. **b) Substrate Overview:** - Structure: This substrate also includes a bromine (Br) atom bonded to a carbon adjacent to a phenyl ring, with a tertiary butyl group as well. - Key Features: In this structure, the bromine atom is on a dash, representing a different stereochemistry at the chiral center compared to substrate a). **E2 Major Product Explanation:** - In E2 reactions, the base removes a hydrogen from the carbon adjacent to the one bearing the leaving group (bromine in these examples), leading to the formation of a double bond. - For substrate a), when treated with a strong base, the likely major product will have the double bond formed between the carbon atoms adjacent to where the bromine was, favoring the formation of the more stable, highly substituted alkene. - Similarly, substrate b) will form a double bond, again favoring the more substituted alkene, with the configuration depending on the stereochemistry of the starting material. These reactions exemplify regioselectivity and stereoselectivity in E2 reactions, often leading to the most stable (Zaitsev) alkene when multiple products are possible.
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