University of Texas

CH 53185

Chapter 17 Carboxylic Acids • The functional group of a carboxylic acid is a carboxyl group. – The general formula for an aliphatic carboxylic acid is RCO2H; that for an aromatic carboxylic acid is ArCO2H. Structure First: Re-Review of Oxidation Reactions • Jones Reagent (H 2CrO 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 ) 2OH…the silver mirror reaction is a qualitative test for aldehydes and an efficient but expensive way to make acids form aldehydes OH O H2CrO4, Acetone H2SO4 OH O OH H2CrO4, Acetone H2SO4 C H O H3C H3C C OH O H2CrO4, Acetone Ag(NH3)2 OH C H O H3C H3C C OH O + Ag0 Examples 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 Nomenclature - IU