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
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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![**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.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F5bd92255-a2a0-4a94-bea6-1b6bd4843a22%2Fe173fc1c-51a8-4069-a8f4-6691bb61355c%2Ftdfm6q_processed.png&w=3840&q=75)
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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