1-1Chemistry 121, Winter 2008, LA Chemistry 121, Winter 2008, LA TechTech
Introduction to Organic Chemistry and BiochemistryIntroduction to Organic Chemistry and Biochemistry Instructor Dr. Upali Siriwardane (Ph.D. Ohio State) E-mail: [email protected] Office: 311 Carson Taylor Hall ; Phone: 318-257-4941;Office Hours: MTW 9:00 am - 11:00 am; TR 9::00 - !0:00 am & 1:00-2:00 pm.December 19, Test 1 (Chapters 12-14)January 2 Test 1 (Chapters 15-16)February 6 (Chapters 17-19)February 27, (Chapters 20-22)March 2, 2009, Make Up Exam:Bring Scantron Sheet 882-E
Chemistry 121(01) Winter 2009
1-2Chemistry 121, Winter 2008, LA Chemistry 121, Winter 2008, LA TechTech
Chapter 16: Carboxylic Acids, Esters, and Chapter 16: Carboxylic Acids, Esters, and Other Acid DerivativesOther Acid Derivatives
SectionsSections
1-3Chemistry 121, Winter 2008, LA Chemistry 121, Winter 2008, LA TechTech
Chapter 16:Carboxylic Acids, Esters, and Other Chapter 16:Carboxylic Acids, Esters, and Other Acid DerivativesAcid Derivatives16.1 Structure of Carboxylic Acids and Their Derivatives16.1 Structure of Carboxylic Acids and Their Derivatives
16.2 IUPAC Nomenclature for Carboxylic Acids16.2 IUPAC Nomenclature for Carboxylic Acids
16.3 Common Names for Carboxylic Acids16.3 Common Names for Carboxylic Acids
16.4 Polyfunctional Carboxylic Acids16.4 Polyfunctional Carboxylic Acids
16.5 "Metabolic" Acids16.5 "Metabolic" Acids
16.6 Physical Properties of Carboxylic Acids16.6 Physical Properties of Carboxylic Acids
16.7 Preparation of Carboxylic Acids16.7 Preparation of Carboxylic Acids
16.8 Acidity of Carboxylic Acids16.8 Acidity of Carboxylic Acids
16.9 Carboxylic Acid Salts16.9 Carboxylic Acid Salts
16.11 Preparation of Esters16.11 Preparation of Esters
16.14 Isomerism for Carboxylic Acids and Esters16.14 Isomerism for Carboxylic Acids and Esters
16.16 Chemical Reactions of Esters16.16 Chemical Reactions of Esters
16.18 Polyesters16.18 Polyesters
16.19 Acid Chlorides and Acid Anhydrides16.19 Acid Chlorides and Acid Anhydrides
16.20 Esters and Anhydrides of Inorganic Acids16.20 Esters and Anhydrides of Inorganic Acids
1-4Chemistry 121, Winter 2008, LA Chemistry 121, Winter 2008, LA TechTech
Carboxylic Acids and Acid Derivatives
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Nomenclature of Carboxylic Acids
The IUPAC system deals with carboxylic acids similar to aldehydes.
Carboxyl group takes priority and it’s carbon assigned the number one.
Suffix: for -ane ending, drop -e and add -oic acid.
There are two ways to identify substituent carbons in carboxylic acid: numbers or Greek letters.
1-6Chemistry 121, Winter 2008, LA Chemistry 121, Winter 2008, LA TechTech
Carboxylic acid examples
• 2-bromopropanoic acid (or -bromopropanoic acid) • 2-methyl butenoic acid • 2,2-dibromopropanoic acid • or , -dibromopropanoic acid or 3-oxopentanoic
acid or 3-ketopentanoic acid - ketopentanoic acid • methanoic acid H-COOH (formic acid)• ethanoic acid CH3COOH (acetic acid)• benzoic acid Ar-COOH
1-7Chemistry 121, Winter 2008, LA Chemistry 121, Winter 2008, LA TechTech
Nomenclature of Esters
Alkyl(R') alkan(R)oate (a two-part name)
R’= Alkyl (R') group is attached to the O
methylethanolate
isopropylbenzoate
ethylbutanolate
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Nomenclature of acid halides
Alkanoyl halide (-oyl halide suffix)
or use common acyl name from acid
E.g. chloride of proponoic acid is named as proponoyl chloride
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Alkanoic anhydride (-oic anhydride suffix)
E.g. anhydride of proponoic acid is named as proponoic anhydride
Nomenclature of Acid Anhydrides
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Metal alkanoate (-oate suffix for anion)
E.g. sodium salt of proponoic acid is
named as sodium proponate
Nomenclature of Carboxylate salts
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Physical properties of carboxylic acidsCarboxyl groups exhibit very strong hydrogen bonding.
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Acidity
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Preparation of carboxylic acids Oxidation of primary alcohol to carboxylic acid.
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Tollen’s and Benedict’s
Oxidation of alkyl side chain substituted on a benzene ring
Oxidation of Aldehydes
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•Hydrolysis of acid chlorides
•Hydrolysis of acid anhydrides
Hydrolysis of esters.
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Carboxylic Acids
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Preparation of esters. Esterification
acid + alcohol ----> ester + H2O
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Esters as Flavors
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Fatty acids and GlyceridesFatty Acids
Glycerides
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Hydrolysis of Glycerides: Saponification
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Reactions of -keto acids.
-keto acids are readily decarboxylated.
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Oxidation of primary alcohols
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Oxidation of secondary and tertiary alcohols