1-1 Chemistry 121, Winter 2008, LA Tech Introduction to Organic Chemistry and Biochemistry Instructor Dr. Upali Siriwardane (Ph.D. Ohio State) Office: 311 Carson Taylor Hall ; Phone: ; 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

1-2 Chemistry 121, Winter 2008, LA Tech Chapter 16: Carboxylic Acids, Esters, and Other Acid Derivatives Sections

1-3 Chemistry 121, Winter 2008, LA Tech 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 Preparation of Esters Isomerism for Carboxylic Acids and Esters Chemical Reactions of Esters Polyesters Acid Chlorides and Acid Anhydrides Esters and Anhydrides of Inorganic Acids

1-4 Chemistry 121, Winter 2008, LA Tech Carboxylic Acids and Acid Derivatives

1-5 Chemistry 121, Winter 2008, LA Tech 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.

1-6 Chemistry 121, Winter 2008, LA Tech 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 CH 3 COOH (acetic acid) benzoic acid Ar-COOH

1-7 Chemistry 121, Winter 2008, LA Tech Nomenclature of Esters Alkyl(R') alkan(R)oate (a two-part name) R’= Alkyl (R') group is attached to the O methylethanolate isopropylbenzoate ethylbutanolate

1-8 Chemistry 121, Winter 2008, LA Tech 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

1-9 Chemistry 121, Winter 2008, LA Tech Alkanoic anhydride (-oic anhydride suffix) E.g. anhydride of proponoic acid is named as proponoic anhydride Nomenclature of Acid Anhydrides

1-10 Chemistry 121, Winter 2008, LA Tech Metal alkanoate (-oate suffix for anion) E.g. sodium salt of proponoic acid is named as sodium proponate Nomenclature of Carboxylate salts

1-11 Chemistry 121, Winter 2008, LA Tech Physical properties of carboxylic acids Carboxyl groups exhibit very strong hydrogen bonding.

1-12 Chemistry 121, Winter 2008, LA Tech Acidity

1-13 Chemistry 121, Winter 2008, LA Tech Preparation of carboxylic acids Oxidation of primary alcohol to carboxylic acid.

1-14 Chemistry 121, Winter 2008, LA Tech Tollen’s and Benedict’s Oxidation of alkyl side chain substituted on a benzene ring Oxidation of Aldehydes

1-15 Chemistry 121, Winter 2008, LA Tech Hydrolysis of acid chlorides Hydrolysis of acid anhydrides Hydrolysis of esters.

1-16 Chemistry 121, Winter 2008, LA Tech Carboxylic Acids

1-17 Chemistry 121, Winter 2008, LA Tech Preparation of esters. Esterification acid + alcohol ----> ester + H 2 O

1-18 Chemistry 121, Winter 2008, LA Tech Esters as Flavors

1-19 Chemistry 121, Winter 2008, LA Tech Fatty acids and Glycerides Fatty Acids Glycerides

1-20 Chemistry 121, Winter 2008, LA Tech Hydrolysis of Glycerides: Saponification

1-21 Chemistry 121, Winter 2008, LA Tech Reactions of  -keto acids.  -keto acids are readily decarboxylated.

1-22 Chemistry 121, Winter 2008, LA Tech Oxidation of primary alcohols

1-23 Chemistry 121, Winter 2008, LA Tech Oxidation of secondary and tertiary alcohols