Lect 13 given Sp 09 - Lecture 13 Chemistry 310N Organic...

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Lecture 13 Chemistry 310N Organic Chemistry II for Prehealth Professionals Unique number: 53185 Tu,Th 12:30-2:00 pm, Welch 2.224 Professor: Jonathan Sessler, Ph.D. sessler@mail.utexas.edu Homework is due today!
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Chapter 17 Carboxylic Acids
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The functional group of a carboxylic acid is a carboxyl group. The general formula for an aliphatic carboxylic acid is RCO 2 H; that for an aromatic carboxylic acid is ArCO 2 H. Structure
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First: Re-Review of Oxidation Reactions Jones Reagent (H 2 CrO 4 in wet acetone) takes primary alcohols to acids and secondary alcohols to ketones--breathalizer test, as demonstrated last time. The Tollen’s Test Ag(NH 3 ) 2 OH…the silver mirror reaction is a qualitative test for aldehydes and an efficient but expensive way to make acids form aldehydes
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OH O H 2 CrO 4 , Acetone H 2 SO 4 O OH H 2 CrO 4 , Acetone H 2 SO 4 C H O H 3 C H 3 C C OH O H 2 CrO 4 , Acetone Ag(NH 3 ) 2 C H O H 3 C H 3 C C O +A g 0 Examples
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Review of Oxidation Reactions -- Cont. Cr(III) in the absence of H 2 O (e.g., pyridinium chlorochromate, PCC; pyridinium dichromate, PDC) allows primary alcohols to be take ONLY to the aldehyde stage (cf. section 10.8.1 in B, F &I) PCC
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Nomenclature - IUPAC IUPAC names: drop the -e from the parent alkane and add the suffix -oic acid . If the compound contains a carbon-carbon double bond, change the infix -an- to -en- .
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And, My “Favorite”, Butyric Acid
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Nomenclature - IUPAC The carboxyl group takes precedence over most other functional groups.
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Nomenclature - IUPAC Dicarboxylic acids: add the suffix -dioic acid to the name of the parent alkane containing both carboxyl groups.
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Nomenclature - IUPAC If the carboxyl group is bonded to a ring, name the ring compound and add the suffix -carboxylic acid . Benzoic acid is the simplest aromatic carboxylic acid. Use numbers to show the location of substituents.
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Nomenclature-Common When common names are used, the letters α, β, γ, δ, etc. are often used to locate substituents.
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Physical Properties In the liquid and solid states, carboxylic acids are associated by hydrogen bonding into dimeric structures.
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This note was uploaded on 06/15/2009 for the course CH 53185 taught by Professor Sessler during the Spring '09 term at University of Texas at Austin.

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Lect 13 given Sp 09 - Lecture 13 Chemistry 310N Organic...

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