Download Acid Derivatives

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
O
C
Succinic
Acid
H2 C
OH
H2 C
OH
C
O
Heat
O
C
H2 C
Succinic
Acid
O
H H
O
H2 C
C
O
Heat
Succinic
Anhydride
O
C
H2 C
O
H2 C
C
O
+ H2 O
O
C
Phthalic
Acid
OH
Heat
OH
C
O
Phthalic
O
Anhydride
C
O
C
O
+ H2O
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-R2
Acid
Ester
O
R1-C-O-R2
+ H 2O
Name R & P
O
CH3-C-OH +
HO-CH3
Acid
Name R & P
O
CH3-C-OH +
HO-CH3
Acid
O
CH3-C
+ H2O
O-CH3
Blah Blah Blah 15.5 days left
O
Methanol
OH + HO-CH3
OH
Salicylic Acid
DHA
O
Methanol
OH + HO-CH3
OH
Salicylic Acid
DHA
O
Methyl Salicate
O-CH3
OH + H2O
Oil of Wintergreen
Esterification
Acetic
Anhydride
O
OH
O
C-CH3
OH + O
Salicylic Acid
O
C-CH3
Acetyl salicylic A
O
Acetic acid
Aspirin
OH O
+
C-CH3
O HO
C-CH3
O
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 H 2O
H2C-O-C-R3
Common Biological Ester
H2C-OH +
-2
HO-PO3
O
HC-OH + HO-C-R2
O
H2C-OH + HO-C-R3
Phosphoglyceride
H2C-O-PO3
-2
O
HC-O-C-R2
+ 3 H2 O
O
H2C-O-C-R3
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
Ester Hydrolysis
O
R1-C-O-R2
O-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-CAcetyl 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-OO
At pH 7 ish
O
O
-O-P-OH & -O-P-OOH
OH
P A Anhydrides
O +
O
HO-P-OH HO-P-OH
OH Heat OH
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 of
Cyclopentyl
benzoate
Hydrolysis of
Butanoic
hexanoic
anhydride
Hydrolysis of
Phenyl
thioacetate
Draw & Name 10
isomers of:
C5H10O2
Each isomer must have a
carboxyl or derivative:
Name
OH
Name
OH
OH