Hydrolysis of T-Butyl Chloride: A Lecture and Lab Experiment
Demonstration: A sample of tert-butyl chloride is added to a mixture of water, isopropanol sodium hydroxide, and universal indicator. The t-butyl chloride undergoes a SN1 reaction hydrolysis, forms HCl and lowers the pH of the mixture causing a change in the color of the indicator. This experiment may use acetone in place of isopropanol.
CH3CCl(CH3)CH3(aq) ↔ CH3C(CH3)CH3+(aq) + Cl−(aq) + H2O(l) ↔ CH3C(CH3)OH2CH3+(aq) + Cl−(aq)↔ CH3COH(CH3)CH3(aq) + HCl(aq)h
Source: UW Card Catalog, North Carolina State Demonstration Paper
Year: 2012 Vol: N/A Page: N/A
Keywords: Hydrolysis, SN1, Acidity, pH, Indicators, Tert-butyl chloride
Rating: 
Hazard: Medium
- Flammable Liquids
- Eye irritation
- Specific target organ toxicity- single exposure – central nervous system
- Corrosive to metals
- Skin corrosive hazard
- Serious eye damage
- Acute aquatic toxicity
- Germ cell mutagenicity
- Carcinogenicity
- Reproductive toxicity
- Electric shock hazard
Effectiveness: Average
- Some connection from demo to course material
- Moderate failure rate
- Time to results is low
- Mild effects are observed by audience
- Secondary effects are observed
- Results are observable with guidance
Difficulty: Medium
- Some intermediate steps to results
- Manipulations are simple form most to perform
- Use of mildly reactive substances
Safety Precautions:
- Eye protection required
- Gloves required
- Avoid exposure to dusts, mists, and vapors
- Perform in a well-ventilated area
- Use UL approved three-prong plug and outlet
- Avoid exposures to open flames or high heat
- Prevent release of reagents to the environment
Class: Types of Organic Reactions, Indicators
Division: Organic Chemistry
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