5. Sketch your TLC plate(s), clearly labeled with the location and identihy of s

Question

5. Sketch your TLC plate(s), clearly labeled with the location and identihy of substances run, the eluent employed, and Rr values. -2.25in product Discussion and conclusion Provide responses to each of the following "questions." 1. What is the identity of each spot in the "product lane of your TLC? Provide chemical names or structures as labels on your TLC sketch above. The toppot is acety l ferrocene '? How pure was your final product? Describe the evidence you have for the purity of the compound. 2. 3. Suppose you found that your final product was contaminated with unreacted ferrocene. Propose at least one method you could use for purifying your acetylferrocene, assuming ferrocene was the only contaminant. Provide as much detail as you can about the procedure you propose to use (e.g. solvents you would use for recrystallization, temperatures you would look for in distillation, etc.). 4. Predict the product of the following reaction 0 AlCls, then H2O

Explanation / Answer

1. The first spot on TLC correspond to the reactant, ferrocenne. The second spot correspond to the reaction mixture consisting of the reactant (ferrocene) and the product (acetylferrocene). THe third spot correspond to the product, acetylferrocene.

2. The final product, acetylferrocene is pure. The compound melts at 81-83oC. IR spectra helps to identify the C=O group of acetyl. It has a CO carbonyl stretching at 1680 cm-1.

3. When the final product, acetylferrocene is contaminated with unreacted ferrocene, it can be purified by column chromatography. Separation is based on the distribution of individual components of the mixture between stationary and mobile phases. Non-polar compounds elute first followed by next level of polar compounds when using column chromatography. During the purification of acetyl ferrocene by column chromatography, hexanes are used to elute the unreacted ferrocene first as a yellow orange band. Upon subsequent elution with (1:1) hexane/CH2Cl2, the acetyl ferrocene (red-orange) starts to move down the column.

4. Normally, the ethyl group in ethylbenzene directs new groups into the 2- and 4- positions (assuming the ethyl group is in the 1- position). But, mostly substitution occurs in the 4- position to give p-ethyl acetophenone.

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