1. Explain why 4-hydroxy-4-methyl-2-pentanone is not a major side- product in th

Question

1. Explain why 4-hydroxy-4-methyl-2-pentanone is not a major side- product in the aldol reaction you performed. 2. Why is the crude product in this experiment washed with sodium bicar- bonate? (Refer to Table 4.1.) 3. Draw all possible geometric isomers of your product. 4. Based on the stoichiometry shown, draw all possible products, including geometric isomers, for the reaction shown below. EtOH NaOH Cl 5. Starting with any aldehyde(s) and acetone, outline a strategy for selec- tively synthesizing the molecule shown below. Explain each step that you would use, including the stoichiometry of the reactants and any reagents and workup conditions. What type of spectral data would you acquire to ensure that you had obtained the desired product? Cl Br

Explanation / Answer

1. In the aldol reaction, after the aldol condensation we get a beta-hydroxyketone product which readily undergoes dehydration reaction to give a more stable conjugated product. Thus the reaction does not produce 4-hydroxy-4-methyl-2-pentanone as the major product.

2. The crude product is washed with NaHCO3 to make the reaction go to completion. The aldol product formed as beta-hydroxyketone is dehydrated in presence of NaHCO3 and gives the conjugated product as the sole product of this reaction by the NaHCO3 wash.

3. Shown below are all geometric isomers of final product formed in 1.

4. Drawn below are all the possible products and the geometric isomers of each in the given aldol reaction

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