Chapter 17-2

Chapter 17-2 - CHEM 262 Wei You Chapter 17. Carboxylic...

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1 CHEM 262 Wei You Chapter 17. Carboxylic Acids (2)
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2 Carbonation of Grignard reagents treatment of a Grignard reagent with carbon dioxide followed by acidification gives a carboxylic acid MgBr C O O C-O  -   [MgBr] + O HCl H 2 O C-O H O Mg 2 + A magnesium carboxylate Cyclopentane- carboxylic acid + Carbon dioxide + Preparation
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3 Acetic acid is synthesized by carbonylation of methanol the carbonylation is exothermic the Monsanto process uses a soluble rhodium(III) salt and HI to catalyze the reaction + O CO CH 3 COH CH 3 OH H° = -138 kJ(33 kcal)/mol Methanol to Acetic Acid
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4 Steps 1 and 2: preparation of the catalyst: Steps 3 and 4: the catalytic cycle [ CH 3 - Rh( CO) I 3 ] - CO [ CH 3 C- Rh( CO) I 3 ] - An acyl-rhodium carbonyl complex CH 3 OH CH 3 COH O O catalytic cycle (3) (4) CH 3 OH HI CH 3 I + H 2 O + CH 3 I Rh( CO) I 2 [CH 3 -Rh(CO)I 3 ] - + A methyl-rhodium carbonyl complex Methanol to Acetic Acid
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5 The carboxyl group is very resistant to reduction it is not affected by catalytic hydrogenation under conditions that easily reduce aldehydes and ketones to alcohols or that reduce alkenes and alkynes to alkanes; it is not reduced by NaBH 4 Lithium aluminum hydride reduces a carboxyl group to a 1° alcohol reduction is carried out in diethyl ether, THF, or other nonreactive, aprotic solvent COH O 1. LiAlH 4 2. H 2 O CH 2 OH LiOH Al(OH) 3 + + 4-Hydroxymethyl-     cyclopentene Reduction
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Chapter 17-2 - CHEM 262 Wei You Chapter 17. Carboxylic...

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