Carbonyl Condensation Reactions羰基缩合反应.ppt

Aldol condensations Carbonyl Condensation Reactions Very General Reaction. What is needed? A Ketone or aldehyde ONE reactant must have a-Hydrogens Base (NaOH) Very General Reaction. Aldol Condensation Reaction Predict the Products Aldol reactions Possible Crossed Aldols One carbonyl has no a-hydrogens Practice making mixed products Aldol reactions with Intramolecular Aldol What would happen? What would happen? Consider carefully Recognizing Aldol Products Product is a b-hydroxy aldehyde or ketone Removing the bond between the Cα – Cβ reveals the carbon units that were joined in the aldol condensation Recognizing Aldol Products The hydroxy becomes a carbonyl How would you make these Compounds by an Aldol Condensation reaction? a b-hydroxy More * NO α-HYDROGENS α α α α α α 1. An α-carbon is the carbon directly attached to the C=O 2. Hydrogens attached to these C are called α-hydrogens C H 3 C O H A c e t a l d e h y d e H O - C H 3 C O H C H 3 C O - H C H 2 C O H H 2 O C H 3 C O H H C H 2 C O H H 2 O C H 3 C O - H C H 2 C O H H O - A l d o l α α α a β-hydroxy aldehyde β C O H H O - S l o w l y a d d O H C a n n o t f o r m e n o l a t e C O H C O H H O H O H C H 3 C H 2 C O H d i l u . H O - C H 2 C O H d i l u . H O - O + + C H 3 C H 2 C O H There are two products for each reaction O O H H H O - O - O H O - O O H O A beta hydroxy ketone or or Remember, five and six membered rings are most stable O H O H β β a β-hydroxy These are: aldehyde and ketone Change the C-OH β β α α Identify the bond between the α- and b-carbon atoms Delete the bond between the α- and b-carbon atoms into a C=O