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: C 5 H 10 O 2

Drill: Draw & Name 4 isomers containing carboxyl groups of: C 6 H 12 O 2

Acid Derivatives

Acid Anhydrides

O O R 1 -C-O-C-R 2

Acid Anhydrides Formed through the dehydration synthesis of two carboxylic acids

Making Anhydrides O O R 1 -C-OH + HO-C-R 2

General Anhydride O O R 1 -C-O-C-R 2 + H 2 O

Determine All O CH 3 -C-OH + O HO-C-CH 3

O CH 3 -C-OH + HO-C-CH 3 O

Diacetic Anhydride O O CH 3 -C-O-C-CH 3 + H 2 O

H 2 C OH H 2 C OH OCCOOCCO Succinic Acid Heat

H 2 C O H H H 2 C O OCCOOCCO Succinic Acid Heat

H 2 C O + H 2 O H 2 C OCCOOCCO Succinic Anhydride

OH OCCOOCCO Phthalic Acid Heat

O O C C + H 2 O O Phthalic Anhydride

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 R 1 -C-O-C-R 2 + H 2 O

Anhydride Hydrolysis O O R 1 -C-O-C-R 2 + H-O H

Two Acids O O R 1 -C-OH + HO-C-R 2

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

Esters

O R 1 -C-O-R 2

Esterification The formation of esters

Ester Formation Dehydration synthesis of alcohols & acids

Esterification O R 1 -C-OH + HO-R 2 Acid

Ester O R 1 -C-O-R 2 + H 2 O

Name R & P CH 3 -C-OH + HO-CH 3 Acid O

Name R & P CH 3 -C-OH + HO-CH 3 Acid O

CH 3 -C + H 2 O O-CH 3 O

O OH + HO-CH 3 OH DHA Methanol Salicylic Acid Blah Blah Blah 15.5 days left

O OH + HO-CH 3 OH DHA Methanol Salicylic Acid

O O-CH 3 OH + H 2 O Methyl Salicate Oil of Wintergreen

Esterification O OH O OH + O Acetic Anhydride Salicylic Acid C-CH 3 O

Acetyl salicylic A O OH O O Acetic acid Aspirin C-CH 3 O HO +

Drill: Draw & name 5 esters that are isomers of C 6 H 12 O 2

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-CH 2 -CH 3 Rum

Octyl acetate O H 3 C-C-O-(CH 2 ) 7 -CH 3 Oranges

Pentyl acetate O H 3 C-C-O-(CH 2 ) 4 -CH 3 Bananas

Ethyl butyrate O H 2 C-C-O-CH 2 -CH 3 CH 2 -CH 3 Pineapples

Pentyl butyrate O H 2 C-C-O-(CH 2 ) 4 -CH 3 CH 2 -CH 3 Apricots

Methyl butyrate O H 2 C-C-O-CH 3 CH 2 -CH 3 Apples

Predict Product O CH 3 -CH 2 -CH 2 -C-OH O + HO-C-CH 3 + Heat

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

Common Biological Ester O H 2 C-OH + HO-C-R 1 O HC-OH + HO-C-R 2 O H 2 C-OH + HO-C-R 3

Triglyceride O H 2 C-O-C-R 1 O HC-O-C-R 2 O + 3 H 2 O H 2 C-O-C-R 3

Common Biological Ester H 2 C-OH + HO-PO 3 -2 O HC-OH + HO-C-R 2 O H 2 C-OH + HO-C-R 3

Phosphoglyceride H 2 C-O-PO 3 -2 HC-O-C-R H 2 O H 2 C-O-C-R 3 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 R 1 -C-O-R 2 base + H 2 O

Ester Hydrolysis O R 1 -C-O-R 2 O-H H

Acid & Alcohol O R 1 -C-OH + HO-R 2

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-R 2 -OH

Acyl Group O R-C-

Acyl Group O CH 3 -C- Acetyl Group

Thioesters O R 1 -C- S-R 2

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 R 1 -C-OH + HS-R 2

Acid & Thiol O R 1 -C-OH + HS-R 2

Thioesters O R 1 -C- S-R 2 + H 2 O

Making a Common Thioester O CH 3 -C-OH + HS-CoA

Making a Common Thioester O CH 3 -C-OH + HS-CoA

Acyl Group O CH 3 -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 OH Heat

P A Anhydrides O O + H 2 O HO-P-O-P-OH OH OH

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

Phosphoesters O HO-P-O-R OH + H 2 O

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

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

Phosphorylation Transfer of this phosphoryl group through phosphoester bonds

Inorganic Ester H 2 C-OH HO-NO 2 HC-OH + HO-NO 2 H 2 C-OH HO-NO 2

Nitroglycerin H 2 C-O-NO 2 HC-O-NO H 2 O H 2 C-O-NO 2

Draw & Name 5 acid or acid derivative containing isomers of: C3H6O3C3H6O3

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 of Cyclopentyl benzoate

Hydrolysis of Butanoic hexanoic anhydride

Hydrolysis of Phenyl thioacetate

Draw & Name 10 isomers of: C 5 H 10 O 2 Each isomer must have a carboxyl or derivative:

Name OH

Name OH