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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Transcribed Image Text:The image displays a chemical reaction that involves the formation of two different products from a common reactant. The instructions state:
"The following reactions give two different products. Show the mechanisms leading to their formation."
### Reaction Details:
1. **First Reaction:**
- Reactant: A cyclohexanone derivative (five-membered ring with a ketone group).
- Reagents: Methanol (CH₃OH) and a proton source (H⁺).
- Product: An acetal of the starting material with methanol, indicated by the addition of methoxy (-OCH₃) and hydroxyl groups (OH).
2. **Second Reaction:**
- Reactant: Same cyclohexanone derivative.
- Reagents: Methoxide ion (CH₃O⁻) and methanol (CH₃OH).
- Product: An ether formation is shown, where methoxy groups are added to the original structure.
### Reaction Mechanisms:
- **Mechanism for First Reaction:**
- The acidic conditions suggest a standard acetal formation mechanism where the ketone undergoes protonation leading to a more reactive electrophilic center. Methanol then attacks, forming a hemiketal, followed by further reaction to form the acetal with the release of water.
- **Mechanism for Second Reaction:**
- The use of methoxide as a nucleophile under basic conditions indicates a nucleophilic attack on the carbonyl carbon. This often proceeds through a single step in basic conditions to quickly form ether linkages by direct displacement of the leaving group.
These reactions illustrate the different pathways a single reactant can undergo based on the nature of the catalytic environment—acidic or basic catalyst—leading to bifurcation in the reaction pathway and formation of structurally different products.
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