one potential issue with the work up is the solubility of the product in water. The solubility of adipic acid in water is 1.4g/100ml. if you started with 150mg of cyclohexanone, how much adipic acid would be produced (100% yield)? How much adipic acid would remain (not washed away) if you washed your product with 1 ml of water?
The reaction suggests 1 mole of cyclohexanone gives rise to 1 mole of adipic acid and is shown below
Molecular weight of Cyclohexanone= 98
moles of cyclohexanone= mass/Molecular weight= 150*10-3/98=0.001531 moles
molecular weight of adipic acid =146 mass of adipic acid formed= 0.001531*146=0.2235gm
solubility of adipic acid = 1.4g/100ml
100ml water dissolves 1.4 gm
1ml water dissolves 1.4/100=0.014gm
when washed with 1ml water, adipic acid remaining= 0.2235-0.014=0.2095gm
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