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12. For each of the following reactions, identify whether you would use hydroxide of tert-butoxide to accomplish the desired transformation: (a) (Ь) Br

12. For each of the following reactions, identify whether you would use hydroxide of tert-butoxide to accomplish the desired transformation: (a) (Ь) Br

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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**12. For each of the following reactions, identify whether you would use hydroxide or tert-butoxide to accomplish the desired transformation:** **(a)** The starting molecule is a chlorinated compound with the structure: - A tertiary carbon bonded to a chlorine atom, two methyl groups, and another alkyl group. The reaction results in the formation of an alkene, indicating an elimination reaction. **(b)** The starting molecule is a brominated compound with the structure: - A tertiary carbon bonded to a bromine atom, two methyl groups, and another alkyl group. The reaction also results in the formation of an alkene, indicating an elimination reaction. **Reaction Explanation:** - The reaction involves the elimination of a halogen atom (chlorine or bromine) from a tertiary carbon, resulting in the formation of a double bond (alkene). **Reagent Consideration:** - **Hydroxide (OH-):** A strong base often used in elimination reactions, usually resulting in E2 mechanisms, especially with secondary and less hindered substrates. - **Tert-butoxide [(CH₃)₃CO-]:** A bulky base which favors elimination over substitution, particularly useful for E2 reactions on hindered substrates, such as tertiary halides, to form less substituted alkenes (Hofmann elimination). In these transformations, tert-butoxide would be an appropriate choice due to the tertiary nature of the substrate, encouraging elimination.
Transcribed Image Text:**12. For each of the following reactions, identify whether you would use hydroxide or tert-butoxide to accomplish the desired transformation:** **(a)** The starting molecule is a chlorinated compound with the structure: - A tertiary carbon bonded to a chlorine atom, two methyl groups, and another alkyl group. The reaction results in the formation of an alkene, indicating an elimination reaction. **(b)** The starting molecule is a brominated compound with the structure: - A tertiary carbon bonded to a bromine atom, two methyl groups, and another alkyl group. The reaction also results in the formation of an alkene, indicating an elimination reaction. **Reaction Explanation:** - The reaction involves the elimination of a halogen atom (chlorine or bromine) from a tertiary carbon, resulting in the formation of a double bond (alkene). **Reagent Consideration:** - **Hydroxide (OH-):** A strong base often used in elimination reactions, usually resulting in E2 mechanisms, especially with secondary and less hindered substrates. - **Tert-butoxide [(CH₃)₃CO-]:** A bulky base which favors elimination over substitution, particularly useful for E2 reactions on hindered substrates, such as tertiary halides, to form less substituted alkenes (Hofmann elimination). In these transformations, tert-butoxide would be an appropriate choice due to the tertiary nature of the substrate, encouraging elimination.
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