Question

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6 Florene Report E2. QUESTIONS, 9 points 1. In a different oxidation reaction isobomool is converted to camphor with a solution of bleach (NaOCI) and acetic acid. The reaction is worked up using liquid-liquid extraction of compounds and analyzed by TLC. Identify which solvent layer in a separatory funnel each compound will be the most soluble by putting (A) Aqueous or (O) Organic under each compound below. 3 pts isoborneol bornylene camphor bleach sodium cetate - NaOCI NaCH.CO) CH,C1, 2. Describe how you assigned compounds to the aqueous and organic layers above. 2pts 3. After separating and drying your reaction mixture in week 1. you rinsed the drying agent with about 3 mL of additional toluene. What is the purpose of rising the drying agent? 2 pts 4. How did increasing solvent polarity change the Rs of fluorene and fluorenone? Cite your data from TLC solvent tests in week I and offer an explanation for your observation. 2 pts Report Total

Answer 1

1) soborneol bomylenc camphor bleach NaOCI sodium acetate Na(CH,00) CH,C1 Organic Organic Aqueous Aqueous (A) Organic (0) (0) (A) Organic (0) (0)

2) "Like dissolves like", this means non-polar substances are most likely to be soluble in non-polar solvents such as organic solvents, whereas, polar (and ionic) substances are most likely to be soluble in the aqueous layer.
Isoborneol is an organic compound with a hydroxyl group, hence it will be more soluble in the organic layer. Similarly, bornylene and camphor are also soluble in the organic layer as they are comparatively less polar. Whereas, NaOCl and NaOAc being ionic in nature are more soluble in water.

3) The drying agent is used to remove traces amount of water from the organic layer. Hence particles of drying agents are surrounded by a majority of the organic layer. There is a good chance of organic substances are also present along with the organic layer around the drying agent. Hence to remove any traces of organic substances that may have trapped in drying layer particles need to be extracted. If not then it will be a loss and your yield may decrease. Hence to ensure this removal of the organic substance you need to rinse the drying agent.

4) To answer this question the TLC data is needed.