Bromination of Saturated and Unsaturated Hydrocarbons
Esterification Using a Dean-Stark Trap
Electrophilic Aromatic Substitution Reaction/ EAS Reaction
Reactivity of Alkanes vs. Aromatic Compounds
Organic Synthesis With Familiar Materials
Extraction of Copper Ions From Solution With Orform®
Reaction Intermediates in Organic Chemistry
Hydrolysis of T-Butyl Chloride: A Lab and Lecture Experiment
Electrophilic Aromatic Substitution Reaction
Description: A set of four Petri dishes is filled with a mixture of TCNQ in Diglyme and placed on an overhead projector table and warmed with the lamp. Portions of Morpholine in Diglyme are added to the four petri dishes. The color of the solution in the dishes is dependent on the species in the liquid. The dye itself is a pale yellows, the first product, the TCNQ anion radical is green, and the first substitution product is dark blue. The third species the second Substitution product, is generated- by step addition of morpholine to the final petri dish, yielding a bright golden color.
Source: Novak, L.P, Brotero, P.P. El Seoud, O.A., Journal of Chemical Education
Year: 1989 Vol: 66 No.12 Page: 1040 – 1041
Keywords: EAS, Intermediate, Substitution, Organic Chemistry, Aromaticity, Conjugation, Delocalization
Rating: 
Hazards: Some
- Flammable liquids
- Reproductive capacity
- Acute toxicity- oral, dermal, inhalation
- Skin corrosion hazard
- Acute aquatic toxicity
- Severe eye damage
- Electric shock hazard
Effectiveness: Good
- Results are observable with guidance
- Good connection from demo to course material
- Mild effects are seen by audience
- Contrast between behavior of systems is notable
- Time to results is medium
- Moderate failure rate
Difficulty: High
- Use of sensitive reagents
- Multi-step procedures
- Demos that require training or extended practice to perform correctly
Safety Precautions:
- Eye protection required
- Nitrite gloves required
- Avoid exposure to dust, vapors, or mists
- Face shield recommended
- Lab coat recommended
- Perform in a well-ventilated
- Absorbent materials on hand
- ABC fire extinguisher required
- Sodium hydroxide or sodium hypochlorite on hand
- Use UL approved three-prong plug and outlet
Class: Types of Organic Reactions
Division: Organic, General
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