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aldol - Experiment 22 THE SOLVENTLESS ALDOL-TYPE...

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Experiment 22: THE SOLVENTLESS ALDOL-TYPE CONDENSATION H 3 CO H 3 CO H O O + NaOH H 3 CO H 3 CO O + H 2 O
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Objectives: To synthesize an α , β unsaturated ketone from an aldehyde and a ketone using solvent-free conditions. To purify the product through a recrystallization. To identify and analyze purity through TLC and melting point analysis. To analyze the product using IR and NMR spectra.
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Before coming to lab… Review these techniques: Recrystallization TLC Analysis Melting Point Analysis
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ALDOL CONDENSATIONS Aldol condensations are nucleophilic additions of an enolate ion, which are strong nucleophiles, to another C=O group under basic conditions. Protonation gives the aldol product. Once formed, the aldol product undergoes dehydration in base. Abstraction of an a proton gives an enolate that can expel an –OH ion to give a conjugated product. Dehydration is usually exothermic because it leads to a very stable conjugated product. C C H O C H H CH 3 α β
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CHEMICAL EQUATION H 3 CO H 3 CO H O O + NaOH H 3 CO H 3 CO O + H 2 O 3,4-dimethoxy  benzaldehyde 1-indanone Aldol Product
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MECHANISM O H H - H 2 O O H +  NaO H O H r e s onanc e OH H + O O H O +  H 2 O O H C H O O O H O H -OH O H C H OH O O -OH - H 2 O O O + NaO H  + H 2 O O Base removes  α
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