6-137. The mixed aldol reaction between propionaldehyde (propanal) and acetone gives an 85% yield of 4-hydroxy-2- hexanone when run in THF at -78 °C with lithium diisopropylamide (LDA, a powerful base). The reaction is carried out by first adding the ketone to the base, cooling the solution, and then adding the aldehyde. (a) Why does this mixed system give essentially a single product? (b) Why is there no self-condensation of the acetone? (c) Why does the system not rapidly go on to dehydrate? (d) Why is the ketone added to the base rather than vice versa? ليك debudes for ketones) has no α-hydrogen atoms. This is

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6-137. The mixed aldol reaction between propionaldehyde (propanal) and acetone gives an 85% yield of 4-hydroxy-2-
hexanone when run in THF at -78 °C with lithium diisopropylamide (LDA, a powerful base). The reaction is carried
out by first adding the ketone to the base, cooling the solution, and then adding the aldehyde.
(a) Why does this mixed system give essentially a single product?
(b) Why is there no self-condensation of the acetone?
(c) Why does the system not rapidly go on to dehydrate?
(d) Why is the ketone added to the base rather than vice versa?
ليك
debudes for ketones) has no α-hydrogen atoms. This is
Transcribed Image Text:6-137. The mixed aldol reaction between propionaldehyde (propanal) and acetone gives an 85% yield of 4-hydroxy-2- hexanone when run in THF at -78 °C with lithium diisopropylamide (LDA, a powerful base). The reaction is carried out by first adding the ketone to the base, cooling the solution, and then adding the aldehyde. (a) Why does this mixed system give essentially a single product? (b) Why is there no self-condensation of the acetone? (c) Why does the system not rapidly go on to dehydrate? (d) Why is the ketone added to the base rather than vice versa? ليك debudes for ketones) has no α-hydrogen atoms. This is
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