Embed Size (px)
Citation preview
Reactions of Reactions of Carboxylic Acids, Carboxylic Acids, Carboxylate Salts,Carboxylate Salts,
andandCarboxylate EstersCarboxylate Esters
Susan F. Hornbuckle
Associate Professor of Chemistry
Clayton State University
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
C
O
OCH2
CH3
Na + H-Cl
Example 1
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
C
O
OCH2
CH3
Na + H-Cl
Example 1
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
C
O
OCH2
CH3
Na + H-Cl
Example 1
C
O
OCH2
CH3
Na
H-Cl
C
O
OCH2
CH3 H + NaCl
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
Example 1
C
O
OCH2
CH3
Na + H-ClC
O
OCH2
CH3 H + NaCl
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
Example 2
C
O
OCH2
CH3
+ NaOHH
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
Example 2
C
O
OCH2
CH3
+ NaOHH
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
Example 2
C
O
OCH2
CH3
+ NaOHH
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
Example 2
C
O
OCH2
CH3
+ NaOHH
C
O
OCH2
CH3 H
H
ONa
C
O
OCH2
CH3
Na + H2O
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
Example 2
C
O
OCH2
CH3 HC
O
OCH2
CH3
Na + H2O+ NaOH
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
Example 3
C
O
OCH2
CH3 CH3 + H2O H2SO4
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
Example 3
C
O
OCH2
CH3 CH3 + H2O H2SO4
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
Example 3
C
O
OCH2
CH3 CH3 + H2O H2SO4
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
Example 3
C
O
OCH2
CH3 CH3 + H2O H2SO4
C
O
OCH2
CH3 CH3
H2SO4 C
O
OCH2
CH3 H+ CH3-O-H
H
OH
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
Example 3
C
O
OCH2
CH3 CH3 + H2O H2SO4 C
O
OCH2
CH3 H+ CH3-O-H
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
Example 4
H2SO4C
O
OCH2
CH3 H+ CH3-O-H
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
Example 4
H2SO4C
O
OCH2
CH3 H+ CH3-O-H
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
Example 4
H2SO4C
O
OCH2
CH3 H+ CH3-O-H
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
Example 4
H2SO4C
O
OCH2
CH3 H+ CH3-O-H
C
O
OCH2
CH3 CH3 + H2O H2SO4
C
O
OCH2
CH3 H
CH3
OH
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
Example 4
C
O
OCH2
CH3 CH3 + H2O H2SO4C
O
OCH2
CH3 H+ CH3-O-H
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
Example 5
C
O
OCH2
CH3 CH3 + H2O NaOH
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
Example 5
C
O
OCH2
CH3 CH3 + H2O NaOH
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
Example 5
C
O
OCH2
CH3 CH3 + H2O NaOH
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
Example 5
C
O
OCH2
CH3 CH3 + H2O NaOH
C
O
OCH2
CH3 CH3
+ CH3-O-H
H
OH
NaOH
C
O
OCH2
CH3 H
H
ONa
C
O
OCH2
CH3
Na + CH3-O-H
Reactions Flow ChartClassify the
reactant.
Carboxylic Acid
Reaction Conditions?
Carboxylate Saltwith an acid
Carboxylate Ester
Reaction Conditions?
Carboxylic Acid + base
“Acid-Base Reaction”
Carboxylic Acid + Alcohol + H2SO4
“Esterification”
Break the bond betweenthe H and the acid and
bond H to the carboxylategroup to form a carboxylic acid.
Carboxylate Ester+ H2O + NaOH
“Saponification”
Carboxylate Ester+ H2O + acid
“Acid Catalyzed Hydrolysis”
Remove the hydrogenfrom the carboxyl groupand bond it to the “O” or the “N” of the base
to form water or anammonium ion,
respectively. Pair thecation with the carboxylate ion.
Remove the OHfrom the carboxyl groupand the H from the O of the alcohol to form H2O.
Form a bond between the O of the alcohol and
the C of the carboxylgroup to form an ester.
Break the C-O of thecarboxylate 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 thecarboxylate 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.
Then remove the hydrogenfrom the carboxyl groupand bond it to the “O” of t he base to form water.
Pair the cation with the carboxylate ion.
Example 5
C
O
OCH2
CH3 CH3 + H2O + CH3-O-HNaOH C
O
OCH2
CH3
Na
![Lability and Basicity of Bipyridine-Carboxylate ...sabrash/seminar/Outside Speaker... · ] (bpH 2 cH = 6′-phosphono-[2,2′-bipyridine]-6-carboxylic acid, L = 4-picoline or isoquinoline)](https://img.pdfslide.net/doc/110x75/61062003ba91955d9f7906a7/lability-and-basicity-of-bipyridine-carboxylate-sabrashseminaroutside-speaker.jpg)
![Very Important Paper | ] “Structural Analogues” of Well ... · Full Paper the presence of a carboxylic acid that provides carboxylate li-gandsandanacidicenvironmenttoavoidprecipitationofMn](https://img.pdfslide.net/doc/110x75/5dd078f006d5421854454fa1/very-important-paper-aoestructural-analoguesa-of-well-full-paper-the-presence.jpg)