Amines can be made by the reduction of nitriles, which in turn can be made from an alkyl halide. Draw the structures of a starting alkyl bromide and the intermediate nitrile that would be used in the synthesis of 3-methylbutylamine (also known as isoamylamine). Do not show free ions. alkyl bromide NC- nitrile Draw the alkyl bromide. Select Draw Templates More C H Br 1. LIAIH4 2. H₂O Erase isoamylamine NH₂ Draw the nitrile. Select Draw Templates More C H N Erase
Amines can be made by the reduction of nitriles, which in turn can be made from an alkyl halide. Draw the structures of a starting alkyl bromide and the intermediate nitrile that would be used in the synthesis of 3-methylbutylamine (also known as isoamylamine). Do not show free ions. alkyl bromide NC- nitrile Draw the alkyl bromide. Select Draw Templates More C H Br 1. LIAIH4 2. H₂O Erase isoamylamine NH₂ Draw the nitrile. Select Draw Templates More C H N Erase
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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
Transcribed Image Text:### Amines Synthesis from Nitriles
Amines can be synthesized by reducing nitriles, which are themselves derived from alkyl halides. In this example, we will explore how to prepare 3-methylbutylamine (also known as isoamylamine) via this method.
#### Reaction Pathway:
1. **Alkyl Bromide to Nitrile:**
- Start with an alkyl bromide which reacts with a cyanide ion (NC⁻) to form a nitrile.
2. **Nitrile to Amine:**
- The nitrile is then reduced using lithium aluminum hydride (LiAlH₄) followed by hydrolysis with water (H₂O) to yield the amine, 3-methylbutylamine.
The chemical structure of 3-methylbutylamine is shown with its chain and amino group (-NH₂).
#### Diagram Explanation:
- **Alkyl Bromide → Nitrile:**
- The substitution of the bromide ion with a cyanide ion results in the formation of a nitrile.
- **Nitrile Reduction:**
- The nitrile undergoes reduction with LiAlH₄ and subsequent hydrolysis with water, transforming into an amine.
#### Drawing Instructions:
- Use the provided drawing tools to sketch the structures.
- **Draw the Alkyl Bromide:**
- Utilize the drawing panel to sketch the alkyl bromide structure with options like "C" for carbon, "H" for hydrogen, and "Br" for bromine.
- **Draw the Nitrile:**
- Construct the nitrile structure using the same panel, replacing bromine with the nitrile group.
This mechanism outlines a critical pathway in organic synthesis, illustrating a method for producing amines from simpler organic compounds.
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