1. Reactions of Alcohols Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University

2. Reactions Flow Chart What are the reaction conditions? K2Cr2O 7 / H2SO4 “Oxidation Conditions” Is the starting alcohol 1 o, 2 o, or 3 o ? 1 o Remove the alpha- hydrogen and the hydroxyl-hydrogen to form an ALDEHYDE. Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. 2 o Remove the alpha- hydrogen and the hydroxyl-hydrogen to form a KETONE. 3 o NO RXN.

3. What are the reaction conditions? K2Cr2O 7 / H2SO4 “Oxidation Conditions” Is the starting alcohol 1 o, 2 o, or 3 o ? 1 o Remove the alpha- hydrogen and the hydroxyl-hydrogen to form an ALDEHYDE. Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. 2 o Remove the alpha- hydrogen and the hydroxyl-hydrogen to form a KETONE. 3 o NO RXN. Example 1

7. What are the reaction conditions? K2Cr2O 7 / H2SO4 “Oxidation Conditions” Is the starting alcohol 1 o, 2 o, or 3 o ? 1 o Remove the alpha- hydrogen and the hydroxyl-hydrogen to form an ALDEHYDE. Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. 2 o Remove the alpha- hydrogen and the hydroxyl-hydrogen to form a KETONE. 3 o NO RXN. Example 2

8. What are the reaction conditions? K2Cr2O 7 / H2SO4 “Oxidation Conditions” Is the starting alcohol 1 o, 2 o, or 3 o ? 1 o Remove the alpha- hydrogen and the hydroxyl-hydrogen to form an ALDEHYDE. Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. 2 o Remove the alpha- hydrogen and the hydroxyl-hydrogen to form a KETONE. 3 o NO RXN.

9. Example 2 What are the reaction conditions? K2Cr2O 7 / H2SO4 “Oxidation Conditions” Is the starting alcohol 1 o, 2 o, or 3 o ? 1 o Remove the alpha- hydrogen and the hydroxyl-hydrogen to form an ALDEHYDE. Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. 2 o Remove the alpha- hydrogen and the hydroxyl-hydrogen to form a KETONE. 3 o NO RXN.

10. Example 2 What are the reaction conditions? K2Cr2O 7 / H2SO4 “Oxidation Conditions” Is the starting alcohol 1 o, 2 o, or 3 o ? 1 o Remove the alpha- hydrogen and the hydroxyl-hydrogen to form an ALDEHYDE. Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. 2 o Remove the alpha- hydrogen and the hydroxyl-hydrogen to form a KETONE. 3 o NO RXN.

11. Example 3 What are the reaction conditions? K2Cr2O 7 / H2SO4 “Oxidation Conditions” Is the starting alcohol 1 o, 2 o, or 3 o ? 1 o Remove the alpha- hydrogen and the hydroxyl-hydrogen to form an ALDEHYDE. Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. 2 o Remove the alpha- hydrogen and the hydroxyl-hydrogen to form a KETONE. 3 o NO RXN.

12. Example 3 What are the reaction conditions? K2Cr2O 7 / H2SO4 “Oxidation Conditions” Is the starting alcohol 1 o, 2 o, or 3 o ? 1 o Remove the alpha- hydrogen and the hydroxyl-hydrogen to form an ALDEHYDE. Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. 2 o Remove the alpha- hydrogen and the hydroxyl-hydrogen to form a KETONE. 3 o NO RXN.

13. Example 3 What are the reaction conditions? K2Cr2O 7 / H2SO4 “Oxidation Conditions” Is the starting alcohol 1 o, 2 o, or 3 o ? 1 o Remove the alpha- hydrogen and the hydroxyl-hydrogen to form an ALDEHYDE. Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. 2 o Remove the alpha- hydrogen and the hydroxyl-hydrogen to form a KETONE. 3 o NO RXN.

14. Example 3 What are the reaction conditions? K2Cr2O 7 / H2SO4 “Oxidation Conditions” Is the starting alcohol 1 o, 2 o, or 3 o ? 1 o Remove the alpha- hydrogen and the hydroxyl-hydrogen to form an ALDEHYDE. Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. 2 o Remove the alpha- hydrogen and the hydroxyl-hydrogen to form a KETONE. 3 o NO RXN.

15. Example 3 What are the reaction conditions? K2Cr2O 7 / H2SO4 “Oxidation Conditions” Is the starting alcohol 1 o, 2 o, or 3 o ? 1 o Remove the alpha- hydrogen and the hydroxyl-hydrogen to form an ALDEHYDE. Insert an oxygen atom in the C-H bond of the carbonyl to form a CARBOXYLIC ACID. 2 o Remove the alpha- hydrogen and the hydroxyl-hydrogen to form a KETONE. 3 o NO RXN.