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Content-Location: file:///C:/116BA2B3/CHEM1152ReactionsofCarboxylicacids,saltsandesters_files/master03.xml
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Slide 1
Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters
Susan F. Hornbuckle
Associate Professor of Chemistry
Clayton State University
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Slide 1
Reaction=
s Flow
Chart
=
Classify the reactant. <=
/span>
Carboxylic Acid&#=
13;
=
;
Reaction Condition=
s?
Carboxylate Salt&=
#13;
with an acid
Carboxylate Ester Reaction Condition=
s?
Carboxylic Acid +
base
=
“Acid-Base
Reaction”
Carbo=
xylic
Acid + Alcohol + H2<=
/span>SO 4
=
;
“Esterifica=
tion”
Break the bond
between
the H and the aci=
d and
bond H to the
carboxylate
group to form a &=
#13;
carboxylic acid. =
Carbox=
ylate
Ester + H 2<=
/span>O + NaOH
=
“Saponificat=
ion”
Carbo=
xylate
Ester + H2O + acid
=
=
;
“Acid Catal=
yzed
Hydrolysis”
Remove the
hydrogen
from the carboxyl
group
and bond it to the
“O”
or the “N&#=
8221;
of the base
to form
water or an ammonium ion, respectively. Pair the cation with the <=
br>
carboxylate ion.
Remove the OH
=
;
from =
the
carboxyl group and the H from th=
e O of
the alcohol to fo=
rm H 2<=
/span>O. &=
#13;
Form a bond betwe=
en
the O of the alco=
hol
and
the C of the
carboxyl
group to form an =
ester.
Break the C-O of
the
carboxylate group.
Break
the H=
-O of
the water. Bond the H to the=
O-R
to form an
alcohol. Bond the OH from =
the
water to the C of=
the
carboxylate group=
.
Break the C-O of
the
carboxylate group.
Break
the H=
-O of
the water. Bond the H to the=
O-R
to form an
alcohol. Bond the OH from the
water to the C of=
the
carbo=
xylate
group. Then remove the
hydrogen
from the carboxyl
group
and bond it to the
“O” of
t he base to form
water.
Pair =
the
cation with the carboxylate i=
on.
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Slide 1
Reaction=
s Flow
Chart
<=
v:shapetype
id=3D"_x0000_t202" coordsize=3D"21600,21600" o:spt=3D"202" path=3D"m,l,2=
1600r21600,l21600,xe">
Classify the reactant. <=
/span>
Carboxylic Acid&#=
13;
=
;
Reaction Condition=
s?
Carboxylate Salt&=
#13;
with an acid
Carboxylate Ester Reaction Condition=
s?
Carboxylic Acid +
base
=
“Acid-Base
Reaction”
Carbo=
xylic
Acid + Alcohol + H2<=
/span>SO 4
=
;
“Esterifica=
tion”
Break the bond
between
the H and the aci=
d and
bond H to the
carboxylate
group to form a &=
#13;
carboxylic acid. =
Carbox=
ylate
Ester + H 2<=
/span>O + NaOH
=
“Saponificat=
ion”
Carbo=
xylate
Ester + H2O + acid
=
=
;
“Acid Catal=
yzed
Hydrolysis”
Remove the hydrogen
from the carboxyl
group
and bond it to the
“O”
or the “N&#=
8221;
of the base
to form
water or an ammonium ion, respectively. Pair the cation with the <=
br>
carboxylate ion.
Remove the OH
=
;
from =
the
carboxyl group and the H from th=
e O of
the alcohol to fo=
rm H 2<=
/span>O. &=
#13;
Form a bond betwe=
en
the O of the alco=
hol
and
the C of the
carboxyl
group to form an =
ester.
Break the C-O of
the
carboxylate group.
Break
the H=
-O of
the water. Bond the H to the=
O-R
to form an
alcohol. Bond the OH from =
the
water to the C of=
the
carboxylate group=
.
Break the C-O of
the
carboxylate group.
Break
the H=
-O of
the water. Bond the H to the=
O-R
to form an
alcohol. Bond the OH from the
water to the C of=
the
carbo=
xylate
group. Then remove the
hydrogen
from the carboxyl
group
and bond it to the
“O” of
t he base to form
water.
Pair =
the
cation with the carboxylate i=
on.
Exam=
ple 1
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Content-Location: file:///C:/116BA2B3/CHEM1152ReactionsofCarboxylicacids,saltsandesters_files/slide0005.htm
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Slide 1
Reaction=
s Flow
Chart
<=
v:shapetype
id=3D"_x0000_t202" coordsize=3D"21600,21600" o:spt=3D"202" path=3D"m,l,2=
1600r21600,l21600,xe">
Classify the reactant. <=
/span>
Carboxylic Acid&#=
13;
=
;
Reaction Condition=
s?
Carboxylate Salt&=
#13;
with an acid
Carboxylate Ester Reaction Condition=
s?
Carboxylic Acid +
base
=
“Acid-Base
Reaction”
Carbo=
xylic
Acid + Alcohol + H2<=
/span>SO 4
=
;
“Esterifica=
tion”
Break the bond
between
the H and the aci=
d and
bond H to the
carboxylate
group to form a &=
#13;
carboxylic acid. =
Carbox=
ylate
Ester + H 2<=
/span>O + NaOH
=
“Saponificat=
ion”
Carbo=
xylate
Ester + H2O + acid
=
=
;
“Acid Catal=
yzed
Hydrolysis”
Remove the hydrogen
from the carboxyl
group
and bond it to the
“O”
or the “N&#=
8221;
of the base
to form
water or an ammonium ion, respectively. Pair the cation with the <=
br>
carboxylate ion.
Remove the OH
=
;
from =
the
carboxyl group and the H from th=
e O of
the alcohol to fo=
rm H 2<=
/span>O. &=
#13;
Form a bond betwe=
en
the O of the alco=
hol
and
the C of the
carboxyl
group to form an =
ester.
Break the C-O of
the
carboxylate group.
Break
the H=
-O of
the water. Bond the H to the=
O-R
to form an
alcohol. Bond the OH from =
the
water to the C of=
the
carboxylate group=
.
Break the C-O of
the
carboxylate group.
Break
the H=
-O of
the water. Bond the H to the=
O-R
to form an
alcohol. Bond the OH from the
water to the C of=
the
carbo=
xylate
group. Then remove the
hydrogen
from the carboxyl
group
and bond it to the
“O” of
t he base to form
water.
Pair =
the
cation with the carboxylate i=
on.
Exam=
ple 1
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Slide 1
Reaction=
s Flow
Chart
<=
v:shapetype
id=3D"_x0000_t202" coordsize=3D"21600,21600" o:spt=3D"202" path=3D"m,l,2=
1600r21600,l21600,xe">
Classify the reactant. <=
/span>
Carboxylic Acid&#=
13;
=
;
Reaction Condition=
s?
Carboxylate Salt&=
#13;
with an acid
Carboxylate Ester Reaction Condition=
s?
Carboxylic Acid +
base
=
“Acid-Base
Reaction”
Carbo=
xylic
Acid + Alcohol + H2<=
/span>SO 4
=
;
“Esterifica=
tion”
Break the bond
between
the H and the aci=
d and
bond H to the
carboxylate
group to form a &=
#13;
carboxylic acid. =
Carbox=
ylate
Ester + H 2<=
/span>O + NaOH
=
“Saponificat=
ion”
Carbo=
xylate
Ester + H2O + acid
=
=
;
“Acid Catal=
yzed
Hydrolysis”
Remove the hydrogen
from the carboxyl
group
and bond it to the
“O”
or the “N&#=
8221;
of the base
to form
water or an ammonium ion, respectively. Pair the cation with the <=
br>
carboxylate ion.
Remove the OH
=
;
from =
the
carboxyl group and the H from th=
e O of
the alcohol to fo=
rm H 2<=
/span>O. &=
#13;
Form a bond betwe=
en
the O of the alco=
hol
and
the C of the
carboxyl
group to form an =
ester.
Break the C-O of
the
carboxylate group.
Break
the H=
-O of
the water. Bond the H to the=
O-R
to form an
alcohol. Bond the OH from =
the
water to the C of=
the
carboxylate group=
.
Break the C-O of
the
carboxylate group.
Break
the H=
-O of
the water. Bond the H to the=
O-R
to form an
alcohol. Bond the OH from the
water to the C of=
the
carbo=
xylate
group. Then remove the
hydrogen
from the carboxyl
group
and bond it to the
“O” of
t he base to form
water.
Pair =
the
cation with the carboxylate i=
on.
Exam=
ple 1
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Slide 1
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Slide 1
Reaction=
s Flow
Chart
<=
p:placeholder
type=3D"object" position=3D"1" size=3D"half"/>
Classify the reactant. <=
/span>
Carboxylic Acid&#=
13;
=
;
Reaction Condition=
s?
Carboxylate Salt&=
#13;
with an acid
Carboxylate Ester Reaction Condition=
s?
Carboxylic Acid +
base
=
“Acid-Base
Reaction”
Carbo=
xylic
Acid + Alcohol + H2<=
/span>SO 4
=
;
“Esterifica=
tion”
Break the bond
between
the H and the aci=
d and
bond H to the
carboxylate
group to form a &=
#13;
carboxylic acid. =
Carbox=
ylate
Ester + H 2<=
/span>O + NaOH
=
“Saponificat=
ion”
Carbo=
xylate
Ester + H2O + acid
=
=
;
“Acid Catal=
yzed
Hydrolysis”
Remove the hydrogen
from the carboxyl
group
and bond it to the
“O”
or the “N&#=
8221;
of the base
to form
water or an ammonium ion, respectively. Pair the cation with the <=
br>
carboxylate ion.
Remove the OH
=
;
from =
the
carboxyl group and the H from th=
e O of
the alcohol to fo=
rm H 2<=
/span>O. &=
#13;
Form a bond betwe=
en
the O of the alco=
hol
and
the C of the
carboxyl
group to form an =
ester.
Break the C-O of
the
carboxylate group.
Break
the H=
-O of
the water. Bond the H to the=
O-R
to form an
alcohol. Bond the OH from =
the
water to the C of=
the
carboxylate group=
.
Break the C-O of
the
carboxylate group.
Break
the H=
-O of
the water. Bond the H to the=
O-R
to form an
alcohol. Bond the OH from the
water to the C of=
the
carbo=
xylate
group. Then remove the
hydrogen
from the carboxyl
group
and bond it to the
“O” of
t he base to form
water.
Pair =
the
cation with the carboxylate i=
on.
Exam=
ple 1
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Slide 1
Reaction=
s Flow
Chart
<=
p:placeholder
type=3D"object" position=3D"1" size=3D"half"/>
Classify the reactant. <=
/span>
Carboxylic Acid&#=
13;
=
;
Reaction Condition=
s?
Carboxylate Salt&=
#13;
with an acid
Carboxylate Ester Reaction Condition=
s?
Carboxylic Acid +
base
=
“Acid-Base
Reaction”
Carbo=
xylic
Acid + Alcohol + H2<=
/span>SO 4
=
;
“Esterifica=
tion”
Break the bond
between
the H and the aci=
d and
bond H to the
carboxylate
group to form a &=
#13;
carboxylic acid. =
Carbox=
ylate
Ester + H 2<=
/span>O + NaOH
=
“Saponificat=
ion”
Carbo=
xylate
Ester + H2O + acid
=
=
;
“Acid Catal=
yzed
Hydrolysis”
Remove the hydrogen
from the carboxyl
group
and bond it to the
“O”
or the “N&#=
8221;
of the base
to form
water or an ammonium ion, respectively. Pair the cation with the <=
br>
carboxylate ion.
Remove the OH
=
;
from =
the
carboxyl group and the H from th=
e O of
the alcohol to fo=
rm H 2<=
/span>O. &=
#13;
Form a bond betwe=
en
the O of the alco=
hol
and
the C of the
carboxyl
group to form an =
ester.
Break the C-O of
the
carboxylate group.
Break
the H=
-O of
the water. Bond the H to the=
O-R
to form an
alcohol. Bond the OH from =
the
water to the C of=
the
carboxylate group=
.
Break the C-O of
the
carboxylate group.
Break
the H=
-O of
the water. Bond the H to the=
O-R
to form an
alcohol. Bond the OH from the
water to the C of=
the
carbo=
xylate
group. Then remove the
hydrogen
from the carboxyl
group
and bond it to the
“O” of
t he base to form
water.
Pair =
the
cation with the carboxylate i=
on.
Exam=
ple 2
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Slide 1
Reaction=
s Flow
Chart
<=
p:placeholder
type=3D"object" position=3D"1" size=3D"half"/>
Classify the reactant. <=
/span>
Carboxylic Acid&#=
13;
=
;
Reaction Condition=
s?
Carboxylate Salt&=
#13;
with an acid
Carboxylate Ester Reaction Condition=
s?
Carboxylic Acid +
base
=
“Acid-Base
Reaction”
Carbo=
xylic
Acid + Alcohol + H2<=
/span>SO 4
=
;
“Esterifica=
tion”
Break the bond
between
the H and the aci=
d and
bond H to the
carboxylate
group to form a &=
#13;
carboxylic acid. =
Carbox=
ylate
Ester + H 2<=
/span>O + NaOH
=
“Saponificat=
ion”
Carbo=
xylate
Ester + H2O + acid
=
=
;
“Acid Catal=
yzed
Hydrolysis”
Remove the hydrogen
from the carboxyl
group
and bond it to the
“O”
or the “N&#=
8221;
of the base
to form
water or an ammonium ion, respectively. Pair the cation with the <=
br>
carboxylate ion.
Remove the OH
=
;
from =
the
carboxyl group and the H from th=
e O of
the alcohol to fo=
rm H 2<=
/span>O. &=
#13;
Form a bond betwe=
en
the O of the alco=
hol
and
the C of the
carboxyl
group to form an =
ester.
Break the C-O of
the
carboxylate group.
Break
the H=
-O of
the water. Bond the H to the=
O-R
to form an
alcohol. Bond the OH from =
the
water to the C of=
the
carboxylate group=
.
Break the C-O of
the
carboxylate group.
Break
the H=
-O of
the water. Bond the H to the=
O-R
to form an
alcohol. Bond the OH from the
water to the C of=
the
carbo=
xylate
group. Then remove the
hydrogen
from the carboxyl
group
and bond it to the
“O” of
t he base to form
water.
Pair =
the
cation with the carboxylate i=
on.
Exam=
ple 2
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Slide 1
Reaction=
s Flow
Chart
<=
p:placeholder
type=3D"object" position=3D"1" size=3D"half"/>
Classify the reactant. <=
/span>
Carboxylic Acid&#=
13;
=
;
Reaction Condition=
s?
Carboxylate Salt&=
#13;
with an acid
Carboxylate Ester Reaction Condition=
s?
Carboxylic Acid +
base
=
“Acid-Base
Reaction”
Carbo=
xylic
Acid + Alcohol + H2<=
/span>SO 4
=
;
“Esterifica=
tion”
Break the bond
between
the H and the aci=
d and
bond H to the
carboxylate
group to form a &=
#13;
carboxylic acid. =
Carbox=
ylate
Ester + H 2<=
/span>O + NaOH
=
“Saponificat=
ion”
Carbo=
xylate
Ester + H2O + acid
=
=
;
“Acid Catal=
yzed
Hydrolysis”
Remove the hydrogen
from the carboxyl
group
and bond it to the
“O”
or the “N&#=
8221;
of the base
to form
water or an ammonium ion, respectively. Pair the cation with the <=
br>
carboxylate ion.
Remove the OH
=
;
from =
the
carboxyl group and the H from th=
e O of
the alcohol to fo=
rm H 2<=
/span>O. &=
#13;
Form a bond betwe=
en
the O of the alco=
hol
and
the C of the
carboxyl
group to form an =
ester.
Break the C-O of
the
carboxylate group.
Break
the H=
-O of
the water. Bond the H to the=
O-R
to form an
alcohol. Bond the OH from =
the
water to the C of=
the
carboxylate group=
.
Break the C-O of
the
carboxylate group.
Break
the H=
-O of
the water. Bond the H to the=
O-R
to form an
alcohol. Bond the OH from the
water to the C of=
the
carbo=
xylate
group. Then remove the
hydrogen
from the carboxyl
group
and bond it to the
“O” of
t he base to form
water.
Pair =
the
cation with the carboxylate i=
on.
Exam=
ple 2
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Content-Location: file:///C:/116BA2B3/CHEM1152ReactionsofCarboxylicacids,saltsandesters_files/slide0012.htm
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Slide 1
Reaction=
s Flow
Chart
<=
p:placeholder
type=3D"object" position=3D"1" size=3D"half"/>
Classify the reactant. <=
/span>
Carboxylic Acid&#=
13;
=
;
Reaction Condition=
s?
Carboxylate Salt&=
#13;
with an acid
Carboxylate Ester Reaction Condition=
s?
Carboxylic Acid +
base
=
“Acid-Base
Reaction”
Carbo=
xylic
Acid + Alcohol + H2<=
/span>SO 4
=
;
“Esterifica=
tion”
Break the bond
between
the H and the aci=
d and
bond H to the
carboxylate
group to form a &=
#13;
carboxylic acid. =
Carbox=
ylate
Ester + H 2<=
/span>O + NaOH
=
“Saponificat=
ion”
Carbo=
xylate
Ester + H2O + acid
=
=
;
“Acid Catal=
yzed
Hydrolysis”
Remove the hydrogen
from the carboxyl
group
and bond it to the
“O”
or the “N&#=
8221;
of the base
to form
water or an ammonium ion, respectively. Pair the cation with the <=
br>
carboxylate ion.
Remove the OH
=
;
from =
the
carboxyl group and the H from th=
e O of
the alcohol to fo=
rm H 2<=
/span>O. &=
#13;
Form a bond betwe=
en
the O of the alco=
hol
and
the C of the
carboxyl
group to form an =
ester.
Break the C-O of
the
carboxylate group.
Break
the H=
-O of
the water. Bond the H to the=
O-R
to form an
alcohol. Bond the OH from =
the
water to the C of=
the
carboxylate group=
.
Break the C-O of
the
carboxylate group.
Break
the H=
-O of
the water. Bond the H to the=
O-R
to form an
alcohol. Bond the OH from the
water to the C of=
the
carbo=
xylate
group. Then remove the
hydrogen
from the carboxyl
group
and bond it to the
“O” of
t he base to form
water.
Pair =
the
cation with the carboxylate i=
on.
Exam=
ple 2
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Slide 1
Reaction=
s Flow
Chart
<=
p:placeholder
type=3D"object" position=3D"1" size=3D"half"/>
Classify the reactant. <=
/span>
Carboxylic Acid&#=
13;
=
;
Reaction Condition=
s?
Carboxylate Salt&=
#13;
with an acid
Carboxylate Ester Reaction Condition=
s?
Carboxylic Acid +
base
=
“Acid-Base
Reaction”
Carbo=
xylic
Acid + Alcohol + H2<=
/span>SO 4
=
;
“Esterifica=
tion”
Break the bond
between
the H and the aci=
d and
bond H to the
carboxylate
group to form a &=
#13;
carboxylic acid. =
Carbox=
ylate
Ester + H 2<=
/span>O + NaOH
=
“Saponificat=
ion”
Carbo=
xylate
Ester + H2O + acid
=
=
;
“Acid Catal=
yzed
Hydrolysis”
Remove the hydrogen
from the carboxyl
group
and bond it to the
“O”
or the “N&#=
8221;
of the base
to form
water or an ammonium ion, respectively. Pair the cation with the <=
br>
carboxylate ion.
Remove the OH
=
;
from =
the
carboxyl group and the H from th=
e O of
the alcohol to fo=
rm H 2<=
/span>O. &=
#13;
Form a bond betwe=
en
the O of the alco=
hol
and
the C of the
carboxyl
group to form an =
ester.
Break the C-O of
the
carboxylate group.
Break
the H=
-O of
the water. Bond the H to the=
O-R
to form an
alcohol. Bond the OH from =
the
water to the C of=
the
carboxylate group=
.
Break the C-O of
the
carboxylate group.
Break
the H=
-O of
the water. Bond the H to the=
O-R
to form an
alcohol. Bond the OH from the
water to the C of=
the
carbo=
xylate
group. Then remove the
hydrogen
from the carboxyl
group
and bond it to the
“O” of
t he base to form
water.
Pair =
the
cation with the carboxylate i=
on.
Exam=
ple 2
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Content-Location: file:///C:/116BA2B3/CHEM1152ReactionsofCarboxylicacids,saltsandesters_files/slide0015.htm
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Slide 1
Reaction=
s Flow
Chart
Classify the reactant. <=
/span>
Carboxylic Acid&#=
13;
=
;
Reaction Condition=
s?
Carboxylate Salt&=
#13;
with an acid
Carboxylate Ester Reaction Condition=
s?
Carboxylic Acid +
base
=
“Acid-Base
Reaction”
Carbo=
xylic
Acid + Alcohol + H2<=
/span>SO 4
=
;
“Esterifica=
tion”
Break the bond
between
the H and the aci=
d and
bond H to the
carboxylate
![3D"Organization](3D"slide0003_image003.gif")
![3D"Organization](3D"slide0004_image005.gif")
![3D"Organization](3D"slide0005_image006.gif")
![3D"Organization](3D"slide0006_image007.gif")
![](3D"slide0013_image018.gif")
![3D"Organization](3D"slide0015_image021.gif")