TECH 707.

Separating a Mixture by Thin-Layer Chromatography (TLC) CHEM 3760 Read and be familiar with the entire procedure (p. 29-38). Consult the handout for Lab Notebook Format. Experimental Notes: Omit Step 1 (p. 35). You will not need to prepare micropipets from capillary tubes, they will be provided. Check your TLC plates before spotting them to ensure that they have a slightly green color under the UV lamp. You will be visualizing your eluted TLC plates by UV lamp. If you dont initially see the three compounds on your TLC plate, check again, sometimes one of the spots takes a while to be visible. We will not use the iodine developing chamber as it generally does not visualize these compounds very well. We will combine steps 2 and 5 (see NOTE 7, p. 38), so that you prepare 5-identical TLC plates (as below, TLC plates #1-5) to be eluted in each of the five different solvents. After you have completed this section and have determined the best solvent for separation, obtain an unknown solution and prepare one last TLC plate (Step 6, as below, TLC plate #6).

TLC plates 1-5

TLC plate 6

biphenyl

benzophenone

unknown, 2 spots

biphenyl

unknown, 1 spot

benzophenone

mixture, 1 spot

benzhydrol

(75 pts) Lab Write-up: (Your lab write-up should be complete down to the ***** line before coming to lab, but will not be collected.) (2 pts) Date and Title of Experiment (2 pts) Objective (2 pts) Structure of the three compoundsbiphenyl, benzophenone, and benzhydrol to be separated by TLC. (2 pts) Table of physical constants for each reactant and product (7 pts) Bulleted outlinetwo-column format (see handout). ************************************************************************************************** (25 pts) Observations and calculations (data recorded during the lab) 1. (5 pts) Note any observations you make about the experiment in the data/observations portion of your bulleted procedure outline. 2. (10 pts) Draw a sketch of each of the 6 TLC plates after UV visualization in your notebook. 3. (10 pts) Calculate the Rf for each compound (biphenyl, benzophenone, and benzydrol) using the TLC plate that gives the best separation (and the same solvent that you used for your unknown). (25 pts) Results and Discussion 1. (5 pts) Which solvent gave the best separation of the mixture of biphenyl, benzophenone, and benzhydrol? What made it the best solvent? Discuss briefly.

mixture, 2 spots

benzophenone

benzhydrol

benzhydrol

biphenyl

OH

2. (10 pts) Draw the three compounds separated in this experiment. Circle the polar functional groups (if any) in each of the compounds. a) What is the order of increasing polarity of these compounds? b) Based on this, which compound would you expect to move furthest up the TLC plate? c) Which compound would you expect to remain closest to the origin? d) What did you observe to be the order of elution of the three compounds examined in this experiment? Was this as you would expect? 3. (5 pts) What is the order of increasing polarity of the different eluting solvents used in this experiment? (Table 1, p. 32) Did the Rf of biphenyl, benzophenone, and benzhydrol change with the different solvents? Why? 4. (5 pts) What was your unknown? How do you knowbriefly explain. (10 pts) Conclusions