Drill: Draw & Name Reactants & Products of:

Drill: Draw & Name Reactants & Products of: • Two oxidations of 1-butanol:

Drill: Draw & Name Reactants & Products of: Oxidation of 2-butanol:

Drill: Draw & Name 3 isomers containing carboxyl groups of: C5H10O2

Drill: Draw & Name 4 isomers containing carboxyl groups of: C6H12O2

Acid Derivatives

Acid Anhydrides

Acid Anhydrides • O O • R1-C-O-C-R2

Acid Anhydrides • Formed through the dehydration of two carboxylic acids

Making Anhydrides • O O • R1-C-OH + HO-C-R2

General Anhydride • O O • R1-C-O-C-R2 • + H2O

Making Anhydrides • O • CH3-C-OH + • O • HO-C-CH3

Diacetic Anhydride • O O • CH3-C-O-C-CH3 • + H2O

Succinic Acid O C C O H2C OH H2C OH Heat

Succinic Anhydride O C C O H2C O + H2O H2C

Phthalic Acid O C C O OH OH Heat

Phthalic Anhydride O C C + H2O O O

Anhydride Hydrolysis • The reverse of the anhydride formation reaction

Acyl Group • O • R-C-

Acyl Group • O • CH3-C- • Acetyl Group

Drill: • Draw the reactants, then predict, draw, & name the product of the dehydration of the combination butanoic acid & propanoic acid.

Esters

Esters • O • R1-C-O-R2

Esterification • The formation of esters

Esterification • O • R1-C-OH + HO-R2 Acid

Ester • O • R1-C-O-R2 • + H2O

O Methanol OH + HO-CH3 OH HCl Salicylic Acid

Methyl Salicate O O-CH3 OH + H2O Oil of Wintergreen

Esterification Acetic Anhydride O OH O C-CH3 C-CH3 OH + O O Salicylic Acid

Acetyl salicylic A O Acetic acid OH O + C-CH3 HO O C-CH3 O Aspirin

Common Esters

Ethyl Formate • O • H-C-O-CH2-CH3 • Rum

Octyl acetate • O • H3C-C-O-(CH2)7-CH3 • Oranges

Pentyl acetate • O • H3C-C-O-(CH2)4-CH3 • Bananas

Ethyl butyrate • O • H2C-C-O-CH2-CH3 • CH2-CH3 • Pineapples

Pentyl butyrate • O • H2C-C-O-(CH2)4-CH3 • CH2-CH3 • Apricots

Methyl butyrate • O • H2C-C-O-CH3 • CH2-CH3 • Apples

Predict Product • O CH3-CH2-CH2-C-OH O + HO-C-CH3 + Heat

Common Biological Ester • O • H2C-OH + HO-C-R1 • O • HC-OH + HO-C-R2 • O • H2C-OH + HO-C-R3

Triglyceride • O • H2C-O-C-R1 • O • HC-O-C-R2 • O + 3 H2O • H2C-O-C-R3

Common Biological Ester • H2C-OH + HO-PO3-2 • O • HC-OH + HO-C-R2 • O • H2C-OH + HO-C-R3

Phosphoglyceride • H2C-O-PO3-2 • O • HC-O-C-R2 • O + 3 H2O • H2C-O-C-R3

Drill: • Draw the reactants, then predict & draw the products of dehydration synthesis when phenol is added to formic acid.

Ester Hydrolysis • Adding water to an ester in acid or base to break it down into an acid & an alcohol

Ester Hydrolysis • O • R1-C-O-R2 base + H2O

Acid & Alcohol • O • R1-C-OH + HO-R2

Polyester • A polymer made up of monomers connected by ester bonds

Making Polyesters • O O • HO-C-R-C-OH • + • HO-R2-OH

Thioesters • O • R1-C- S-R2

Thioesters • In thioesters, the single bonded oxygen is replaced with sulfur

Making Thioesters • Addition of a thiol to an acid or an anhydride

Drill: Draw & Name Reactants & Products of: