Organic Chemistry- Hydrolysis of T-Butyl Chloride: A Lecture and Lab Experiment

Bromination of Saturated and Unsaturated Hydrocarbons

Blue Bottle

Dehydration of Sugar by Sulfuric Acid

Disappearing Coffee Cup

Formation of a Silver Mirror

Models 360

Nylon 6 – 10

Organic Synthesis With Familiar Materials

Oxidation of Primary, Secondary, Tertiary Alcohols

Oxidation of Luminol

Polyurethane Foam

Slime

Underwater Fireworks: Chlorination of Acetylene

Carbide Lamp

Differences in Miscibility of Organic Alcohols With Increasing Chain Length

Combustion of Cellulose Nitrate (Guncotton)

Different Smells of Carvone Isomers

Distinguishing Between HD and LD Polyethylene

Enviro-bond: Cleaning Oil Spills

Esterification Using a Dean-Stark Trap

Ethanol Cannon

Happy/Sad Balls

IR Demonstration I – Atomic Coupling

IR Demonstrations II – Molecular Vibrations

IR Demonstration III – Molecular Vibrations

Making a Rubber Ball from Latex

Plastic Samples

Reaction Intermediates in Organic Chemistry

Reducing Sugars and Fehling’s Solution

Rod Climbing by a Polymer Solution

Rotating Rainbows

Silly Putty

Soap Emulsifies Hydrocarbons

Superabsorbent Polyacrylate Gel

Tubeless Siphon

Alkimers

Aniline Hydrochloride-Formaldehyde Polymer

Phenol-Formaldehyde Polymer

Saponification

Relative Reactivity of Reducing Agents

Inductive Effect

Optical Activity of Racemic Mixtures With Limonene

Electrophilic Aromatic Substitution Reaction/EAS Reaction

Reactivity of Alkanes vs. Aromatic Compounds

Relationship of Absorbed Light to Observed Color

Density and Miscibility of Liquids

Extraction of Copper Ions from Solution with Orform®

Gel Formation with Sodium Alginate and Calcium Chloride

Ozonolysis

Hydrolysis of T-Butyl Chloride: A Lecture and Lab Experiment

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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