Drill: Draw & Name Reactants & Products of: Oxidations of 1-butanol in 2 steps:

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 + HO-C-CH3

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

Succinic Acid O C H2C OH Heat

Succinic Anhydride O C H2C O + H2O

Phthalic Acid O C OH Heat

Phthalic Anhydride O C C + H2O O

The reverse of the anhydride formation reaction 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

The formation of esters Esterification The formation of esters

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

Ester O R1-C-O-R2 + H2O

Name R & P O CH3-C-OH + HO-CH3 Acid

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 OH + O O Salicylic Acid

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

Drill: Draw & name 5 esters that are isomers of C6H12O2

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 + HO-C-CH3 + Heat

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

Triglyceride O H2C-O-C-R1 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 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

A polymer made up of monomers connected by ester bonds 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

Acid & Thiol O R1-C-OH + HS-R2

Acid & Thiol O R1-C-OH + HS-R2

Thioesters O R1-C- S-R2 + H2O

Making a Common Thioester CH3-C-OH + HS-CoA

Making a Common Thioester CH3-C-OH + HS-CoA

Acyl Group O CH3-C-S-CoA Acetyl CoA

Phosphoric Acid O HO-P-OH OH

At pH 7 ish O O -O-P-OH & -O-P-O- OH OH

P A Anhydrides O + O HO-P-OH HO-P-OH OH OH Heat

P A Anhydrides O O + H2O HO-P-O-P-OH OH OH

Phospho Esters O HO-P-OH + HO-R OH Heat

Phosphoesters O HO-P-O-R OH + H2O

Phosphodiesters O HO-P-OH + HO-R OH + H-O-R

Phosphodiesters O HO-P-O-R O-R + 2 H2O

Transfer of this phosphoryl group through phosphoester bonds Phosphorylation Transfer of this phosphoryl group through phosphoester bonds

Inorganic Ester H2C-OH HO-NO2 HC-OH + HO-NO2

Nitroglycerin H2C-O-NO2 HC-O-NO2 + 3 H2O

Draw & Name 5 acid or acid derivative containing isomers of: C3H6O3

Drill: Draw the reactant, then predict, draw, & name the products for the hydrolysis of Propylthioacetate.

Acid Review

Be familiar with the common acids for matching

Be familiar with how to oxidize alcohols

Be familiar with DH rxns making acid derivatives

Be familiar with hydrolysis of acid derivatives

Be able to draw & name isomers with carboxyls

Name OH

Name OH