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 synthesis of two carboxylic acids

Making Anhydrides O O

R1-C-OH + HO-C-R2

General Anhydride O O

R1-C-O-C-R2

+ H2O

Determine All O

CH3-C-OH +

O

HO-C-CH3

O

CH3-C-OH +

HO-C-CH3

O

Diacetic Anhydride O O

CH3-C-O-C-CH3

+ H2O

H2C OH H2C OH

OC

CO

SuccinicAcid

Heat

H2C O H HH2C O

OC

CO

SuccinicAcid

Heat

H2C O + H2OH2C

OC

CO

SuccinicAnhydride

OH

OH

OC

CO

PhthalicAcid

Heat

O

OC

C + H2OO

PhthalicAnhydride

Drill: Draw the reactants, then predict, draw, &

name the organic product in the dehydration of

propanoic acid & butanoic acids.

Anhydride Hydrolysis

•The reverse of the anhydride

formation reaction

Anhydride Hydrolysis

•The hydrolysis of an anhydride forms 2 acids

Anhydride Hydrolysis

O O

R1-C-O-C-R2

+ H2O

Anhydride Hydrolysis

O O

R1-C-O-C-R2

+ H-O H

Two Acids O O

R1-C-OH + HO-C-R2

Drill:• Draw the reactants, then

draw, & name the product of the dehydration synthesis of butanoic acid & propanoic acid.

Esters

Esters O

R1-C-O-R2

Esterification•The formation

of esters

Ester Formation•Dehydration synthesis of

alcohols & acids

Esterification O

R1-C-OH + HO-R2Acid

Ester O

R1-C-O-R2

+ H2O

Name R & P CH3-C-OH +

HO-CH3Acid

O

Name R & P CH3-C-OH +

HO-CH3Acid

O

CH3-C + H2O

O-CH3

O

O

OH + HO-CH3

OH DHA

Methanol

Salicylic Acid

Blah Blah Blah 15.5 days left

O

OH + HO-CH3

OH DHA

Methanol

Salicylic Acid

O

O-CH3

OH + H2O

Methyl Salicate

Oil of Wintergreen

EsterificationO

OH O

OH + O

AceticAnhydride

Salicylic Acid

C-CH3

C-CH3 O

Acetyl salicylic AO

OH O

O

Acetic acid

Aspirin

C-CH3

OC-CH3

HO+

Drill: Draw & name 5 esters

that are isomers of C6H12O2

Organic HW• Draw & Name reactants &

products in the dehydration synthesis between the following:

• Phenol & acetic acid

• Cyclohexanol & formic acid

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

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

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 EsterH2C-OH + HO-PO3

-2

O

HC-OH + HO-C-R2

O

H2C-OH + HO-C-R3

Phosphoglyceride H2C-O-PO3

-2

HC-O-C-R2

+ 3 H2O

H2C-O-C-R3

O

O

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-R2base + H2O

Ester Hydrolysis O

R1-C-O-R2O-H

H

Acid & Alcohol O

R1-C-OH + HO-R2

Drill: Draw the reactants, then predict, draw, & name

the products when acetic acid & phenol go through a

dehydration synthesis reaction.

Polyester•A polymer made up

of monomers connected by ester

bonds

Making Polyesters O O

HO-C-R-C-OH

+

HO-R2-OH

Acyl Group

O

R-C-

Acyl Group

O

CH3-C-

Acetyl Group

Thioesters O

R1-C- S-R2

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

Making Thioesters Dehydration synthesis 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

O

CH3-C-OH + HS-CoA

Making a Common Thioester

O

CH3-C-OH + HS-CoA

Acyl Group

O

CH3-C-S-CoA

Acetyl CoA

Schedule•Tomorrow: Lab

•Next Day: Review

•Next Day: Test

Organic HW• Draw reactants, then name & draw

products of the hydrolysis of:

• Ethylpropanoate

• Phenylthiobutanoate

• Aceticformic anhydride

Phosphoric Acid O

HO-P-OH

OH

Phosphate O

-O-P-O-

O-

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 OHHeat

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

Phosphorylation•Transfer of this phosphoryl group

through phosphoester bonds

Inorganic Ester H2C-OH HO-NO2

HC-OH + HO-NO2

H2C-OH HO-NO2

Nitroglycerin H2C-O-NO2

HC-O-NO2 + 3 H2O

H2C-O-NO2

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.

Carboxylic Acid Review for

Tomorrow’s Test

Be familiar with the

common acids for matching

Be familiar with how to

oxidize alcohols

Strong oxidation of 1-decanol

Be familiar with DH Syn rxns making

acid derivatives

Acetic acid + formic acid +

DHA

Propanoic acid + methanol +

DHA

Butanoic acid + ethanthiol

+ DHA

Be familiar with hydrolysis

of acid derivatives

Hydrolysis ofCyclopentyl

benzoate

Hydrolysis ofButanoic hexanoic anhydride

Hydrolysis ofPhenyl

thioacetate

Draw & Name 10 isomers of:

C5H10O2

Each isomer must have a carboxyl or derivative:

Name

OH

Name

OH

OH