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1. Give the type of reaction, mechanism with curved arrows, and products for the reaction below: Br `NH2 100 °C

1. Give the type of reaction, mechanism with curved arrows, and products for the reaction below: Br `NH2 100 °C

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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**Question**: Give the type of reaction, mechanism with curved arrows, and products for the reaction below: **Reaction**: - **Reactant**: A brominated alkane with a tertiary butyl group (a central carbon bonded to three methyl groups and a bromine atom). - **Reagent**: Ethylamine (CH₃CH₂NH₂) at 100°C. This reaction involves a nucleophilic substitution where the ethylamine acts as a nucleophile, replacing the bromine atom connected to the carbon. **Detailed Mechanism**: 1. **Nucleophilic Attack**: The lone pair on the nitrogen atom of ethylamine attacks the carbon atom bonded to the bromine, forming a new C-N bond while displacing the bromine atom. 2. **Leaving Group Departure**: The bromine leaves as a bromide ion (Br⁻), resulting in elimination from the carbon center. **Product**: The primary product is a tertiary amine where the bromine has been replaced by the ethylamine group attached to the tertiary carbon center. This type of reaction is typically an S_N2 mechanism since it involves a direct displacement of the leaving group by the nucleophile. However, due to the steric hindrance of the tertiary center, it may also exhibit S_N1 characteristics. A detailed analysis considering reaction conditions is necessary to confirm the exact mechanism pathway.
Transcribed Image Text:**Question**: Give the type of reaction, mechanism with curved arrows, and products for the reaction below: **Reaction**: - **Reactant**: A brominated alkane with a tertiary butyl group (a central carbon bonded to three methyl groups and a bromine atom). - **Reagent**: Ethylamine (CH₃CH₂NH₂) at 100°C. This reaction involves a nucleophilic substitution where the ethylamine acts as a nucleophile, replacing the bromine atom connected to the carbon. **Detailed Mechanism**: 1. **Nucleophilic Attack**: The lone pair on the nitrogen atom of ethylamine attacks the carbon atom bonded to the bromine, forming a new C-N bond while displacing the bromine atom. 2. **Leaving Group Departure**: The bromine leaves as a bromide ion (Br⁻), resulting in elimination from the carbon center. **Product**: The primary product is a tertiary amine where the bromine has been replaced by the ethylamine group attached to the tertiary carbon center. This type of reaction is typically an S_N2 mechanism since it involves a direct displacement of the leaving group by the nucleophile. However, due to the steric hindrance of the tertiary center, it may also exhibit S_N1 characteristics. A detailed analysis considering reaction conditions is necessary to confirm the exact mechanism pathway.
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