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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![**Reaction Mechanism: Hydrolysis of Ethylene Oxide**
**Objective:**
Detail the mechanism for the hydrolysis of ethylene oxide using hydroxide ion (-OH) and water (H2O) to produce ethylene glycol.
**Reaction Overview:**
- **Reactants:** Ethylene oxide (C2H4O), Hydroxide ion (-OH), and Water (H2O)
- **Products:** Ethylene glycol (C2H6O2)
**Mechanism Steps:**
1. **Nucleophilic Attack:**
- The hydroxide ion (-OH) attacks the less hindered carbon atom in the three-membered ring of ethylene oxide. This is due to the ring strain and the electrophilic nature of the carbon atoms.
2. **Opening of the Ring:**
- The nucleophilic attack leads to the opening of the epoxide ring. The oxygen in the ring gains an additional electron pair, becoming a negatively charged alkoxide ion.
3. **Protonation:**
- The negatively charged oxygen (alkoxide ion) is protonated by a water molecule. This step regains the stability and results in the formation of ethylene glycol.
**Final Product:**
- **Ethylene Glycol (HO-CH2-CH2-OH):**
- A glycol with two hydroxyl (-OH) groups, signifying the transformation of the epoxide ring into a diol.
**Notes:**
- The reaction is a typical example of base-catalyzed ring opening of an epoxide.
- The reaction helps illustrate the concept of nucleophilic substitution and the stability gained by ring opening.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F7237bf46-4025-4c4f-b170-df7369a74fb6%2Ff71c3689-2643-4bf8-820e-a4b5861f7bd6%2Fjhom7r_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Reaction Mechanism: Hydrolysis of Ethylene Oxide**
**Objective:**
Detail the mechanism for the hydrolysis of ethylene oxide using hydroxide ion (-OH) and water (H2O) to produce ethylene glycol.
**Reaction Overview:**
- **Reactants:** Ethylene oxide (C2H4O), Hydroxide ion (-OH), and Water (H2O)
- **Products:** Ethylene glycol (C2H6O2)
**Mechanism Steps:**
1. **Nucleophilic Attack:**
- The hydroxide ion (-OH) attacks the less hindered carbon atom in the three-membered ring of ethylene oxide. This is due to the ring strain and the electrophilic nature of the carbon atoms.
2. **Opening of the Ring:**
- The nucleophilic attack leads to the opening of the epoxide ring. The oxygen in the ring gains an additional electron pair, becoming a negatively charged alkoxide ion.
3. **Protonation:**
- The negatively charged oxygen (alkoxide ion) is protonated by a water molecule. This step regains the stability and results in the formation of ethylene glycol.
**Final Product:**
- **Ethylene Glycol (HO-CH2-CH2-OH):**
- A glycol with two hydroxyl (-OH) groups, signifying the transformation of the epoxide ring into a diol.
**Notes:**
- The reaction is a typical example of base-catalyzed ring opening of an epoxide.
- The reaction helps illustrate the concept of nucleophilic substitution and the stability gained by ring opening.
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