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Unformatted text preview: weekend, and will be discussed in lecture on Monday… Both reactions we have just discussed are equilibrium reactions. Which side of the reaction is favored at equilibrium??? Consider the data below for the following general reaction: R C R' O + H 2 O OH C OH R' R K eq 2.8 x 10 4 Cl 3 CCH=O too large to measure (CF 3 ) 2 C=O 37 ClCH 2 CH=O 10 (ClCH 2 ) 2 C=O 8.3 x 10 –3 PhCH=O 1.2 x 10 –7 Ph 2 C=O 0.5–1.0 (CH 3 ) 2 CHCH=O 6.6 x 10 –6 1.0 CH 3 CH=O 1.4 x 10 –3 (CH 3 ) 2 C=O 2.2 x 10 3 CH 2 =O K eq Ketone K eq Aldehyde Ph C C H 3 O Some observations : • Aldehydes undergo nucleophilic addition more readily than ketones • Nearby electronegative groups make carbonyl addition more favorable • Aromatic substituents make carbonyl addition less favorable...
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- Spring '08
- Iverson
- Carbonyl, ketone, Nucleophilic addition, Aldehyde
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