Transcript CHEM 121: chapter 16

Chemistry 121(01) Winter 2009
Introduction 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
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Chapter 16: Carboxylic Acids, Esters, and
Other Acid Derivatives
Sections
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Chapter 16:Carboxylic Acids, Esters, and Other
Acid Derivatives
16.1 Structure of Carboxylic Acids and Their Derivatives
16.2 IUPAC Nomenclature for Carboxylic Acids
16.3 Common Names for Carboxylic Acids
16.4 Polyfunctional Carboxylic Acids
16.5 "Metabolic" Acids
16.6 Physical Properties of Carboxylic Acids
16.7 Preparation of Carboxylic Acids
16.8 Acidity of Carboxylic Acids
16.9 Carboxylic Acid Salts
16.11 Preparation of Esters
16.14 Isomerism for Carboxylic Acids and Esters
16.16 Chemical Reactions of Esters
16.18 Polyesters
16.19 Acid Chlorides and Acid Anhydrides
16.20 Esters and Anhydrides of Inorganic Acids
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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.
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Carboxylic acid examples
2-bromopropanoic acid (or a-bromopropanoic acid)
2-methyl butenoic acid
2,2-dibromopropanoic acid
or a, a-dibromopropanoic acid or 3-oxopentanoic
acid or 3-ketopentanoic acid b- ketopentanoic acid
• methanoic acid H-COOH (formic acid)
• ethanoic acid CH3COOH (acetic acid)
• benzoic acid Ar-COOH
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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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Nomenclature of Acid Anhydrides
Alkanoic anhydride (-oic anhydride suffix)
E.g. anhydride of proponoic acid is named
as proponoic anhydride
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Nomenclature of Carboxylate salts
Metal alkanoate (-oate suffix for anion)
E.g. sodium salt of proponoic acid is
named as sodium proponate
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Physical properties of carboxylic acids
Carboxyl groups exhibit very strong hydrogen bondin
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Acidity
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Preparation of carboxylic acids
Oxidation of primary alcohol to carboxylic acid.
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Oxidation of Aldehydes
Tollen’s and Benedict’s
Oxidation of alkyl side chain
substituted on a benzene ring
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Hydrolysis of esters.
•Hydrolysis of acid chlorides
•Hydrolysis of acid anhydrides
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Carboxylic Acids
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Preparation of esters. Esterification
acid +
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alcohol ---->
ester
+
H 2O
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Esters as Flavors
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Fatty acids and Glycerides
Fatty Acids
Glycerides
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Hydrolysis of Glycerides: Saponification
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Reactions of b-keto acids.
b-keto acids are readily decarboxylated.
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Oxidation of primary alcohols
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Oxidation of secondary and tertiary alcohols
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