Template for Electronic Submission of Organic Letters
chem 1321 Stereochemical Analysis of the Reduction of Benzyl lab
1. You are given a mixture containing two compounds, A and B. Both compounds have a solubility of 1 g/ 100 mL of solvent at 20 °C and 16 g/ 100 mL of solvent at 100 °C. The sample is composed of 3.5 g of A and 10 g of B. At 100 °C the entire sample just dissolves in a minimum amount of solvent. The solution is cooled to 20 °C and crystals are collected. Calculate the composition of the crystals and the yield of the process. What is the composition of the mother liquor?
2. If the crystals obtained in question (1) are recrystallized from 100 mL of solvent, what will be the yield and composition of the crystals obtained?
3. A student dissolves 80 mg of a crude product in 4.5 mL (the minimum required) of methanol at 25 °C. She cools the solution in an ice bath and obtains crystals. The crystals are recovered by filtration and rinsed with 0.5 mL of ice-cold methanol. After drying, the weight of the crystals is 5 mg. Why was the recovery so poor? What could she do to improve the process?
4. When butanoic acid reacts with sodium borohydride, 1-butanol is not obtained. However, bubbling is still observed and heat is produced.
a. Why is 1-butanol not obtained?
b. What is the product of this reaction?
5. Predict the configurations of each stereocentre in the product of the following and provide a justification
for your choice.