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
Show the mechanism for the following reaction.
Transcribed Image Text:The image illustrates a chemical reaction involving two reactants in a two-step synthesis process, resulting in an 80% yield of the product.
### Reactants:
1. **First Reactant**:
- Structure: A carbon backbone with an amide group and a tertiary butyl group. The amide group includes a proline derivative ("Pro") with an N-H bond.
- Functional Group: Alcohol (OH) group attached to the tertiary carbon.
2. **Second Reactant**:
- Structure: A ring with four carbon atoms and one nitrogen atom (pyrrolidinium chloride).
- Substituents:
- An OH group
- A positively charged nitrogen atom
- A methoxycarbonyl group (CO2Me)
- A chloride ion (Cl^−)
### Product:
- The product retains the proline derivative and incorporates the pyrrolidine ring from the second reactant. The nitrogeneous ring is integrated with the carbon structure from the first reactant.
- Functional Groups:
- An OH group attached to the ring
- A methoxycarbonyl group (CO2Me)
- The product maintains the amide bond.
### Reaction Details:
- **Process**: The transformation occurs over two steps.
- **Yield**: The overall reaction yield is 80%.
This reaction is an example of skilled organic synthesis, where a complex molecule is built from simpler structures. The process showcases the use of typical organic chemistry techniques and considerations such as maintaining functional groups and careful yield management.
Expert Solution
Introduction
The given reaction occurs in presence of base.
Step 1: Production of amine from ammonium salt in presence of base.
Step 2: Attack of amine on carbonyl carbon of carboxylic acid group and formation of amide bond.
Mechanism: Step 1
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