318-14 - Organic Lecture Series Organic Lecture Series...

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Unformatted text preview: Organic Lecture Series Organic Lecture Series Organic Lecture Series Organic Lecture Series 1 CH 318 N LECTURE 14 Textbook Assignment: Chapter 17 Homework (for credit): POW 6 posted Today’s Topics: Carboxylic Acids-intro, structure Notice & Announcements: Organic Lecture Series Organic Lecture Series Organic Lecture Series Organic Lecture Series 2 Carboxylic Acids Carboxylic Acids Organic Lecture Series Organic Lecture Series Organic Lecture Series Organic Lecture Series 3 • The functional group of a carboxylic acid is a carboxyl group – the general formula for an aliphatic carboxylic acid is RCOOH; that for an aromatic carboxylic acid is ArCOOH COOH CO 2 H O O H C O O H Alternative representations for a carboxyl group Structure Structure Organic Lecture Series Organic Lecture Series Organic Lecture Series Organic Lecture Series 4 • IUPAC names: drop the - e from the parent alkane and add the suffix - oic acid oic acid – if the compound contains a carbon-carbon double bond, change the infix - an an- to - en en- HCOOH CH 3 COOH 3-Methylbutanoic acid (Isovaleric acid) Ethanoic acid (Acetic acid) Methanoic acid (Formic acid) OH O Propenoic acid (Acrylic acid) trans- 3-Phenylpropenoic acid (Cinnamic acid) trans- 2-Butenoic acid (Crotonic acid) OH O OH O OH O Nomenclature Nomenclature Organic Lecture Series Organic Lecture Series Organic Lecture Series Organic Lecture Series 5 • The carboxyl group takes precedence over most other functional groups 5-Oxohexanoic acid 4-Aminobutanoic acid ( R )-5-Hydroxyhexanoic acid OH O OH O OH O H 2 N OH O OH O OH γ-hydroxybutyric Acid GHB 4 3 2 5 OH O α β γ δ 1 Organic Lecture Series Organic Lecture Series Organic Lecture Series Organic Lecture Series 6 – dicarboxylic acids: add the suffix - dioic acid dioic acid to the name of the parent alkane containing both carboxyl groups HO OH O Propanedioic acid (Malonic acid) Ethanedioic acid (Oxalic acid) O HO OH O O Hexanedioic acid (Adipic acid) Pentanedioic acid (Glutaric acid) Butanedioic acid (Succinic acid) O OH O HO OH O HO O HO OH O O Nomenclature Nomenclature Organic Lecture Series Organic Lecture Series Organic Lecture Series Organic Lecture Series 7 – if the carboxyl group is bonded to a ring, name the ring compound and add the suffix - carboxylic acid carboxylic acid – benzoic acid is the simplest aromatic carboxylic acid – use numbers to show the location of substituents COOH COOH HOOC 3 2 1 2-Cyclohexenecarboxylic acid trans- 1,3-Cyclopentanedicarboxylic acid COOH COOH OH COOH COOH COOH COOH Benzoic acid 2-Hydroxybenzoic acid (Salicylic acid) 1,2-Benzenedicarboxylic acid (Phthalic acid) 1,4-Benzenedicarboxylic acid (Terephthalic acid) Organic Lecture Series Organic Lecture Series Organic Lecture Series Organic Lecture Series 8 –when common names are used, the letters α, β, γ, δ, α, β, γ, δ, α, β, γ, δ, α, β, γ, δ, etc. are often used to locate substituents L-alanine] [( S )- α-Aminopropionic acid; ( γ-Aminobutyric acid, GABA)...
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This note was uploaded on 03/23/2010 for the course CH 310n taught by Professor Iverson during the Spring '08 term at University of Texas.

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318-14 - Organic Lecture Series Organic Lecture Series...

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