Lecture 33 - α-halo carbonyl compounds(23.7C •...

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1 Reading for Wednesday Chapter 24: 24.1-24.3 ARIS Quiz #7 Available Wednesday Due Sunday April 24 at 11:59 PM Mon. 6:00-7:30 pm MAL 3092 Tues. 2:30-4:00 PM MAL 2007 Wed. 5:00-6:30 PM MAL 2001 Thurs. 9:30-10:50 AM MAL 1003 Sat. 11:30 AM-1:00 PM MAL 2007 PLUS Sessions THIS WEEK Chapter 23 Substitution Reactions of Carbonyl Compounds at the α Carbon Halogenation at the α -Carbon (23.7) α -H can be replaced by Cl, Br or I using Cl 2 , Br 2 or I 2 as reagent Acid-catalyzed reaction allows monohalogenation Base-catalyzed reaction difficult to stop after one halogenation Rxns of
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Unformatted text preview: α-halo carbonyl compounds (23.7C) • β-Elimination to give α , β-unsaturated carbonyl compounds • Typical reagents: Li 2 CO 3 and LiBr in DMF • S N 2 with various nucleophiles, including amines Malonic Ester Synthesis (23.9) • A way to synthesize carboxylic acids starting from the β-diester diethyl malonate, CH 2 (CO 2 Et) 2 • Sequence of reactions: • 1) Deprotonation • 2) Alkylation of enolate (two alkyl groups can be added sequentially) • 3) Hydrolysis of the ester groups and decarboxylation...
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