classes-fall07-30BID19-Chem30b-Homework-Chapter17and18

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Manashi Chatterjee Ph.D. Fall 2007 Chem 30B – Fall 2007 Homework: Week 10 Chapter 17 17.1, 17.2, 17.3, 17.4, 17.5, 17.6, 17.7, 17.8, 17.12, 17.15, 17.16, 17.17, 17.18, 17.19, 17.20, 17.21, 17.22, 17.24, 17.25, 17.26, 17.27, 17.28, 17.32,17.33, 17.34, 17.35 – 17.43 Key points: Presence of electron withdrawing group near the carboxyl group decreases the p K a and increases the acidity. chloroacetic acid is more acidic than acetic acid. O-H in Phenols and carboxylic acids are acidic; however O-H of alcohol is neutral. Phenols are weaker acids than carboxylic acids. Carboxylic acids react with NaOH, NH 3 , NaHCO 3 to form salts (R-COO - ; water-soluble) Phenols react with NaOH but not with NaHCO 3 (H 2 CO 3 formed is stronger acid than phenol and equilibrium favors starting material). Alcohols do not react with NaOH or NaHCO 3 to form salts . These acid base reactions can be used to separate alcohols, acids and phenols from a mixture. (pg 666, fig.17.1). What do you use to make RO - (alkoxides) from alcohols? Na or K metal or NaH Preparation of Carboxylic acids: Primary alcohols are easily oxidized to aldehyde which can be further oxidized to acids using Chromic acid.
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