Lecture 23. The Aldol Condensation. an Aldol! April 12, 2018 O H O H - Chemistry 328N
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1 Lecture 23 The Aldol Condensation - b a an Aldol! April 12, 2018
2 Exam III - Wed April 18 WEL PM Covers thru today omework ydrolysis Reactions Synthesis Get an A!!!
3 Lithium diisopropylamide (LDA) LDA converts simple esters quantitatively to the corresponding enolate. C 3 C 2 C 2 CC 3 + pk a ~ 22 I Li + C 3 C 2 CCC 3 + N[C(C 3 ) 2 ] 2 pk a ~ 36 Li + C 3 C 3 C N C C 3 C 3
4 Lithium diisopropylamide (LDA) Enolates generated from esters and LDA can be alkylated. C 3 C 2 CCC 3 C 3 C 2 I C 3 C 2 CCC 3 C 2 C 3 (92%)
5 Classical Claisen Condensation An excellent path to b-keto esters 2C 3 CC 2 C 3 1. NaC 2 C C 3 CC 2 CC 2 C 3 Two moles of ethyl acetate condense to give ethyl 3-oxobutanoate or ethyl acetoacetate aka acetoacetic ester
6 A versatile synthesis of b-ketoesters and symmetrically substituted acetones A C 2 C C 2 C 3 A C 2 C C C C 2 C 3 A 3 + eat A C 2 C C 2 A A C 2 C C 2 + C 2 + C 2 C 3 Acetone A
7 Alkylation of Acetoacetic Ester gives unsymmetrically substituted acetone
8 Acetoacetic Ester Synthesis C 3 C R 1 C R 2??
9 Ketone Synthesis Let s work another example together C 3 C 3 C 3
10 Intramolecular Claisen Condensation: The Dieckmann Reaction Walter Dieckmann
11 Example C 3 C 2 CC 2 C 2 C 2 C 2 CC 2 C 3 1. NaC 2 C CC 2 C 3
12 via C 3 C 2 CC 2 C 2 C 2 C 2 CC 2 C 3 NaC 2 C 3 C 3 C 2 CC 2 C 2 C 2 CCC 2 C 3
13 via C 3 C 2 CC 2 C 2 C 2 CCC 2 C 3
14 via C 3 C 2 2 C 2 C C C 2 CCC 2 C 3 C 3 C 2 CC 2 C 2 C 2 CCC 2 C 3
15 via C 3 C 2 2 C 2 C C C 2 CCC 2 C 3
16 via C 3 C 2 2 C C CCC 2 C 3 This works well for 5 and 6 membered rings C 3 C 2 2 C + C 2 2 C C CCC 2 C 3 2 C C 2
17 via C 3 C 2 2 C 2 C C C 2 CCC 2 C 3 The product is the stable carbanion prior to acidification C 3 C C C C CC 2 C 3 2 C C 2
18 The Malonic Ester Synthesis Versatile Synthesis of Carboxylic acids R C C R '
19 Malonic Ester C 3 C 2 C C C C2 C 3 Malonic ester is another name for diethyl malonate. The "malonic ester synthesis" uses diethyl malonate as a reactant for the preparation of carboxylic acids.
20 Dialkylation C 3 C 2 CC 2 CC 2 C 3 1. NaC 2 C 3 2. C 3 Br C 3 C 2 CCCC 2 C 3 C 3
21 C 3 C 2 CCCC 2 C 3 C 3 1. NaC 2 C 3 2. C 3 (C 2 ) 8 C 2 Br C 3 C 2 CCCC 2 C 3 C 3 (C 2 ) 8 C 2 C 3
22 C 3 C 2 CCCC 2 C 3 C 3 (C 2 ) 8 C 2 C 3 C 3 (C 2 ) 8 C 2 CC 1. Na, heat, -C 2 C 3
23 Malonic Ester Synthesis??
24 The Aldol Condensation The product of an aldol condensation is a b-hydroxyaldehyde nucleophilic acyl substitution is not possibe here.why?? - b a an Aldol! {Aldehyde / Alcohol}
25 Loss of water! Aldol products are easily dehydrated so the major product is an a,b-unsaturated aldehyde or ketone D - b a
26 E 2 like Elimination 2 The reaction actually proceeds via the resonance stabilized enolate anion and unlike the E2, it proceeds in a stepwise fashion!
27 A Note about Aldol Reactions aldol reactions are reversible and, particularly for ketones, there is often little aldol present at equilibrium. K eq for dehydration is generally large and, if reaction conditions bring about dehydration, good yields of product can be obtained It takes special efforts to isolate an Aldol the product is generally the a,b -unsaturated aldehyde or ketone
28 Aldol condensation - D - D - Ph Ph D Ph Ph
29 Ph Ph
30 Crossed Aldol Reactions In a crossed aldol reaction, one kind of molecule provides the enolate anion and another kind provides the carbonyl group C 3 C 2 C + C 3 CC 2 C - Mess!! C 3 In most cases, this makes a big fat mess!!
31 The Crossed Aldol Reaction
32 Crossed Aldol Reactions Crossed aldol reactions only work if: one of the reactants has no a-hydrogen and, therefore, cannot form an enolate anion and the other reactant has a very reactive carbonyl group, namely an aldehyde C Formaldehyde C Benzaldehyde C Furfural (C 3 ) 3 CC 2,2-Dimethylpropanal Look no a-hydrogens. so no enolate anions!!
33 Let s discuss a plan for actually running a crossed aldol reaction Does the addition sequence matter?? What goes into the pot first, second and third?
34 The Signature Page Claisen Condensation: b-ketoesters Dieckmann: Cyclic b-ketoesters Acetoacetic ester synthesis: decorated acetones Malonic ester synthesis: decorated acetic acids Aldol: a, b-unsaturated aldehydes and ketones Grignard Reaction: Alcohols, etc.
35 From what?? 3 C 3 C
36 Aldol reactions of ketones 2C 3 CC 3 2% 98% C 3 CC 2 CC 3 C 3 the equilibrium constant for aldol addition reactions of ketones is usually unfavorable but can be driven by dehydration C 3 CC 2 CC 3 C 3 - C 3 C=C CC 3 C 3
37 Aldol Reactions Intramolecular aldol reactions (when the enolate anion and the carbonyl acceptor are in the same molecule) are most a successful a C 3 for formation C 3 of fiveand six-membered K - 2 rings C 3 2,7-ctanedione C 3 C 3 C 3
38 Intramolecular Aldol Condensation Na 2 C 3, 2 heat (96%) ketones give very good yields of aldol condensation products when the reaction is intramolecular and driven by dehydration
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