Chemistry 121 01 winter 2009
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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.

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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.

Chemistry 121(01) Winter 2009

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


Chapter 16 carboxylic acids esters and other acid derivatives

Chapter 16: Carboxylic Acids, Esters, and Other Acid Derivatives

Sections


Chapter 16 carboxylic acids esters and other acid derivatives1
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



Nomenclature of carboxylic acids
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.


Carboxylic acid examples
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


Nomenclature of esters
Nomenclature of Esters

  • Alkyl(R') alkan(R)oate (a two-part name)

  • R’= Alkyl (R') group is attached to the O

  • methylethanolate

  • isopropylbenzoate

  • ethylbutanolate


Nomenclature of acid halides
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


Nomenclature of acid anhydrides
Nomenclature of Acid Anhydrides

  • Alkanoic anhydride (-oic anhydride suffix)

  • E.g. anhydride of proponoic acid is named as proponoic anhydride


Nomenclature of carboxylate salts
Nomenclature of Carboxylate salts

  • Metal alkanoate (-oate suffix for anion)

  • E.g. sodium salt of proponoic acid is

  • named as sodium proponate


Physical properties of carboxylic acids
Physical properties of carboxylic acids

  • Carboxyl groups exhibit very strong hydrogen bonding.



Preparation of carboxylic acids
Preparation of carboxylic acids

  • Oxidation of primary alcohol to carboxylic acid.


Oxidation of aldehydes
Oxidation of Aldehydes

  • Tollen’s and Benedict’s

  • Oxidation of alkyl side chain substituted on a benzene ring


Hydrolysis of esters
Hydrolysis of esters.

  • Hydrolysis of acid chlorides

  • Hydrolysis of acid anhydrides



Preparation of esters esterification
Preparation of esters. Esterification

  • acid + alcohol ----> ester + H2O



Fatty acids and glycerides
Fatty acids and Glycerides

  • Fatty Acids

  • Glycerides



Reactions of b keto acids
Reactions of b-keto acids.

  • b-keto acids are readily decarboxylated.




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