Carboxylic Acid and Derivatives

preparation of carboxylic acids

-can be prepared from primary alcohols or aldehydes

-can be produced from oxidation of primary alcohols to aldehydes and then to carboxylic acids

Reagents: a) RCH2Br + (1) NaCN (2)H3O+, heat

b) RBr + (1) Mg (2) CO2 (3) H3O+

Carboxylic Acid Reactions

1. Reduction (LiALH4/ NH4Cl) = 1° alcohol

2. Heat = acid anhydride

3. ROH (alcohol & acidic condition) = ester

4. SoCl2 = acid halide (Cl-carbonyl-R)

Preparation of Acid Chloride

COOH + SOCl2

Reaction of Acid Chloride (ROH Pyridine)

Reaction of Acid Chloride (xs NH3)

Reaction of Acid Chloride (xs RNH2)

Reaction of Acid Chloride (xs R2NH)

Reaction of Acid Chloride (xs (1)LAH (2)H3O+)

Reaction of Acid Chloride (LA(OR)H, H3O+)

Reaction of Acid Chloride (xs RMgBr, H3O+)

Reaction of Acid Chloride (R2CuLi)

Preparation of Acid Anhydrides

COOH + (NaOH, CH3COCl) or (Heat)

Reaction of Acid Anhydride (ROH)

Reaction of Acid Anhydride (xs NH3)

Reaction of Acid Anhydride (xs RNH2)

Reaction of Acid Anhydride (xs R2NH)

Reaction of Acid Anhydride (xs (1)LAH (2)H3O+)

Reaction of Acid Anhydride (LA(OR)H, H3O+)

Reaction of Acid Anhydride (R2CuLi)

Reaction of Acid Anhydride (xs RMgBr, H3O+)

Preparation of Ester

a) NaOH, RI

b) H+, ROH

c) ROH, Pyridine

Reactions of Esters (NH3)

Reactions of Esters (xs (1)LAH (2)H3O+)

Reactions of Esters (DIBAH, H3O+)

Reactions of Esters (xs RMgBr, H3O+)

Reactions of Esters (H3O+ or with NaOH/heat)

Preparation of Amides

COCl + 2 NH3

Reactions of Amides (H3O+/heat or with NaOH)

Reactions of Amides (xs LAH, H2O)

Preparation of Nitriles

a) RCH2Br + NaCN

b) RCOCl + SOCL2 (-SO2, 2HCL)

Reactions of Nitriles (H3O+/heat or with NaOH)

Reaction of Nitriles (RMgBr, H3O+)

Reaction of Nitriles (xs LAH, H2O)