Chemistry 130 course documents archive

Derivatives guidelines

Carboxylic Acids (Pasto 2nd ed. pp. 341–345)

1. Amides
   
2. Esters
   

Alcohols and Phenols (Pasto 2nd ed. pp. 307–308)

1. Urethanes
   
2. Esters
   

Aldehydes and Ketones (Pasto 2nd ed. pp. 328–333)

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Primary and Secondary Amines (Pasto 2nd ed. pp. 358–360)

1. Sulfonamides
   
2. Amides
   
   
3. Thioureas
   
4. HCl Salts

Tertiary Amines (Pasto 2nd ed. pp. 360–363) — form salts

1. Methiodides
   
2. HCl Salts
3. Picrates*
   

Amides (Pasto 2nd ed. pp. 370–371)

1. Hydrolysis

Aryl Halides

1. Nitration (Pasto 2nd ed. pp. 287, 300)
2. Sulfonation → Sulfonamide (Pasto 2nd ed. pp. 300, 319)
3. Side Chain Oxidation (Pasto 2nd ed. pp. 288, 300)
4. Picrates*

Aromatic Hydrocarbons

1. Nitration (Pasto 2nd ed. pp. 286–287)
2. Oxidation (Pasto 2nd ed. p. 288)
3. Picrates*

Aromatic Nitro Compunds

1. Reduction (Pasto 2nd ed. p. 376)
2. Nitration (Pasto 2nd ed. pp. 287, 377)
3. Bromination (Pasto 2nd ed. pp. 319, 377)
4. Alkyl Side Chain Oxidation (Pasto 2nd ed. pp. 288, 377)

Esters (Pasto 2nd ed. pp. 349–351)

1. Hydrolysis

Aromatic Ethers

1. Bromination (Pasto 2nd ed. p. 319)
2. Sulfonation (Pasto 2nd ed. p. 319)
3. Nitration (Pasto 2nd ed. p. 287)
4. Picrates *

Nitriles (Pasto 2nd ed. p. 373)

1. Hydrolysis

* Pasto no longer recommends the preparation of picrate derivatives because picric acid and its complexes are explosive. If you have to make a picrate derivative, talk to your TA first about safety, and see Pasto and Johnson, Organic Structure Determination, on Reserve in Swain library for a general procedure. Picrates have been made successfully in the past.