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:**Title: Conversion of Cyclopentanone to Cyclopentenol using Acid Catalysis**
**Objective:**
To propose a mechanism for the conversion of cyclopentanone to cyclopentenol using hydronium ion (\( \text{H}_3\text{O}^+ \)).
**Chemical Reaction:**
The reaction involves the transformation of a ketone functional group (cyclopentanone) into an enol (cyclopentenol) through acid catalysis.
**Reactants and Products:**
- **Reactant:** Cyclopentanone (a five-membered ring with a ketone group)
- **Acid Catalyst:** \(\text{H}_3\text{O}^+\) (hydronium ion)
- **Product:** Cyclopentenol (a five-membered ring with an alcohol and an adjacent double bond)
**Mechanism Overview:**
1. **Protonation of the Carbonyl Oxygen:**
- The carbonyl oxygen in cyclopentanone is protonated by \(\text{H}_3\text{O}^+\), increasing the electrophilic character of the carbonyl carbon.
2. **Formation of a Carbocation:**
- The protonated carbonyl group can lead to the formation of a carbocation at the alpha carbon through the removal of a proton.
3. **Double Bond Formation:**
- The alpha carbocation undergoes rearrangement, forming a double bond through the loss of a proton from the adjacent carbon.
4. **Deprotonation and Enol Formation:**
- A water molecule deprotonates the intermediate to yield cyclopentenol, completing the conversion.
The process is facilitated by acid catalysis, which increases the reactivity of the carbonyl group, allowing for the formation of the enol product. This type of transformation is an example of keto-enol tautomerism, where a ketone is converted into its corresponding enol form.
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