Laboratory Videos

Unit 1 - Substitution and Elimination

1. Cyclohexene from Cyclohexanol (Lab #1)

2. Alcohol Bromination Using PBr₃

3. Dehydration of 2-Methyl-2-Butanol

4. Dehydration of Glycerol to Acrolein

5. Dehydration of 2-Methylcyclohexanol

6. Phenol to Anisole via Williamson Ether Synthesis

Unit 2 - Radical Reactions

1. Benzylic Bromination using NBS (Lab #2)

2. Photobromination of Alkylbenzenes

3. Benzylic Chlorination using TCCA

Unit 3 - Simple Aromatic Reactions

1. Friedel-Crafts Acylation of Ferrocene (Lab #3)

2. Bromination of Benzene

3. Nitration of Benzene

4. Reduction of Nitrobenzene to Aniline Using Sn + HCl

5. Sulfonation of Toluene

6. Friedel-Crafts Acylation of Toluene

Unit 4 - Complex Aromatic Reactions

1. Synthesis of Azo Violet Dye (Lab #4)

2. Nitration of Phthalic Anhydride

3. Iodination of Salicylamide

4. Friedel-Crafts Acylation of Anisole

5. Synthesis of Para Red Dye

6. Chlorobenzene from Aniline via Sandmeyer Reaction

Unit 5 - Acyl Substitutions

1. Synthesis of Aspirin from Salicylic Acid (Lab #5)

2. Chemiluminescence via Acyl Substitution

3. Esterification Using Acid Chloride

4. Making Bar Soap via Acyl Substitution

5. Making Phthalic Anhydride from Vinyl Gloves

6. Preparation of Banana Flavoring from 1-Pentanol

7. Preparation of Wintergreen from Salicylic Acid

8. Preparation of Grape Flavoring from Anthranilic Acid

9. Synthesis of a Pain Reliever from Aniline

10. Synthesis of Benzocain from PABA

Unit 6 - Carbonyl Additions, Organometallics

1. Almond Oil to Cinnamon Oil via Wittig Reaction (Lab #6)

2. Preparation of Benzyl Alcohol from Benzaldehyde

3. Preparation of Chlorobutanol via Carbonyl Addition

4. Synthesis of Phenolphthalein (Acid-Base Indicator)

5. Grignard Reaction of Benzoin and Methylmagensium Iodide

6. Preparation of Benzoic Acid via Grignard Reaction

Unit 7 - Oxidations and Reductions

1. Reduction of Vanillin Using NaBH₄ (Lab #7)

2. Wolff-Kishner Reduction of Isatin Using a Microwave

3. Reductive Amination Using Sodium Triacetoxyborohydride

4. Oxidation of 1-Butanol Using KMnO₄

5. Oxidation of 1-Propanol Using Potassium Dichromate

6. Ketone from Alcohol via Swern Oxidation

7. Ozonolysis of Styrene

Unit 8 - Reactions at the Carbonyl α Carbon

1. Synthesis of Sunscreen via Aldol Condensation (Lab #8)

2. Aldol Condensation of Vanillin and Acetone

3. Synthesis of Indigo Dye via Aldol Condensation

4. Decarboxylation of Salicylic Acid

5. Preparation of Chloroform via Haloform Reaction

Field Trip - 1D + 2D Spectroscopic Analysis

1. Pre-Lab Videos

2. IR Spectroscopy

3. NMR Spectroscopy

4. COSY and HSQC Analysis