Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle...
-
Upload
christine-parsons -
Category
Documents
-
view
222 -
download
1
Transcript of Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle...
![Page 1: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/1.jpg)
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
![Page 2: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/2.jpg)
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.
![Page 3: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/3.jpg)
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
![Page 4: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/4.jpg)
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
![Page 5: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/5.jpg)
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
![Page 6: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/6.jpg)
C
O
OCH2
CH3
Na
H-Cl
C
O
OCH2
CH3 H + NaCl
![Page 7: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/7.jpg)
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
![Page 8: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/8.jpg)
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
![Page 9: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/9.jpg)
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
![Page 10: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/10.jpg)
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
![Page 11: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/11.jpg)
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
![Page 12: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/12.jpg)
C
O
OCH2
CH3 H
H
ONa
C
O
OCH2
CH3
Na + H2O
![Page 13: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/13.jpg)
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
![Page 14: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/14.jpg)
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
![Page 15: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/15.jpg)
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
![Page 16: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/16.jpg)
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
![Page 17: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/17.jpg)
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
![Page 18: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/18.jpg)
C
O
OCH2
CH3 CH3
H2SO4 C
O
OCH2
CH3 H+ CH3-O-H
H
OH
![Page 19: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/19.jpg)
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
![Page 20: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/20.jpg)
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
![Page 21: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/21.jpg)
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
![Page 22: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/22.jpg)
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
![Page 23: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/23.jpg)
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
![Page 24: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/24.jpg)
C
O
OCH2
CH3 CH3 + H2O H2SO4
C
O
OCH2
CH3 H
CH3
OH
![Page 25: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/25.jpg)
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
![Page 26: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/26.jpg)
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
![Page 27: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/27.jpg)
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
![Page 28: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/28.jpg)
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
![Page 29: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/29.jpg)
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
![Page 30: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/30.jpg)
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
![Page 31: Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.](https://reader036.fdocuments.us/reader036/viewer/2022062309/56649f2a5503460f94c43cab/html5/thumbnails/31.jpg)
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