9 Aldol Reaction9羟醛缩合反应.PDF

? Professors Kathleen V. Kilway and Andrea Drew, Department of Chemistry, University of Missouri – Kansas City, 2007 – CHEM 322L 9. Aldol Reaction M. Jones: Condensation Reactions, Aldol reaction, Chapter 17, Section 3, pgs 840-850. This procedure has been adapted from the microscale procedure described in the third edition of Macroscale and Microscale Organic Experiments by Kenneth L. Williamson (Houghton Mifflin, Boston, 1999). Background Aldol Reaction. In the experiment, you will perform a base-catalyzed, condensation reaction using benzaldehyde and acetone (see Figure 1). A condensation reaction is one, which condenses two or more molecules to make one single compound. O CO H 2 + H3C CH3 NaOH M.W. 40.01 HOH CC CC HH Benzaldehyde bp 178-179 oC density 1.04 g/mL Acetone (2-propanone) bp 56 oC density 0.790 g/mL Dibenzalacetone (1,5-Diphenyl-1,4pentadien-3-one), mp 110-112 oC Figure 1. The overall reaction. First lets define some different types of compounds. An aldehyde is a molecule with an R-HC=O structure. There is a carbonyl group (C=O). The carbon of the carbonyl group is flanked by a hydrogen (H) and an R group (R does not equal H). A ketone is a molecule with an R2C=O. The R groups do not have to be the same. In this reaction, two molecules of benzaldehyde (aldehyde) are condensed with one molecule of acetone (ketone). Acetone acts as a nucleophile which adds to the carbonyl carbon of benzaldehyde). The first step in the reaction is to form the nucleophile, which is an enolate ion (Figure 2). This is a deprotonation step where a hydroxide ion pulls off a proton from the alpha carbon (carbon adjacent to the carbonyl carbon) to yield a resonance-stabilized enolate. The nucleophile adds to the carbonyl carbon of benzaldehyde in step 2. The resulting alkoxide CHEM 322L Experiment 9: Aldol Reaction 1 CHEM 322L ion is protonated in step 3 to form the true Aldol product which has both alcohol (OH) and carbonyl (C=O) functionalities. O OO H3C CH2 H3C CH2 H3C CH2 +