Question

Procedure Part A:

Oxone reaction: Dissolve 0.40 g Oxone ® in 2.0 mL of water by

shaking vigorously, but carefully, in a sealed vial. (SAFETY: Be sure that the flask is

sealed well. Oxone ® solution is strongly oxidizing and should not come into contact

with skin.) Dissolve 50 ?L of cyclohexene in 2.0 mL of acetone in a small Erlenmeyer

flask. Cool the cyclohexene solution in an icebath, then add the oxone solution dropwise

over 5 minutes with swirling in the icebath. Remove the Erlenmeyer flask from the

icebath and allow the reaction to sit for at least 15 minutes. (This is a good point to begin

the permanganate reaction.) After 15-30 minutes, add about 0.1 mL of conc. HCl to the

reaction dropwise with swirling. Allow the reaction to sit for about 10 minutes, swirling

occasionally.

Procedure Part B:

Potassium permanganate reaction: Dissolve 100 mg of KMnO4 in

4.0 mL of 0.1 M NaOH solution in a small Erlenmeyer flask. Cool the KMnO4 solution

in an icebath. Dissolve 50 ?L of cyclohexene in 2.0 mL of t-butanol in a separate

container. Quickly add the cyclohexene solution into the potassium permanganate. Swirl

the flask in the icebath for 3-5 minutes. Remove the Erlenmeyer flask from the icebath

and allow to sit for 10 minutes.

Procedure Part C:

Thin Layer Chromatography: Obtain a TLC plate. Mark the plate

with four marks, two for each reaction mixture. Spot the crude reaction mixtures lightly.

It may be hard to spot the KMnO4 slurry, but keep trying, you may find it easier if you

use a slightly wider capillary for this one. Allow the plate to dry for a couple of minutes,

or use a heat gun to gently dry the aqueous spots. Develop the plate in a chamber with

ethyl acetate as the eluent. Remove it from the chamber and mark the solvent front. Stain

the plate using anisaldehyde stain, and heat the plate gently to develop the spots. The cis

isomer should stain red, and have an Rf value of ~0.37, the trans isomer should stain blue,

and have an Rf value of ~0.31.

Questions

1. Draw a sketch of the TLC analysis for both reactions.

2. Calculate the Rf of both products formed.

3. Using you text and any other information you can find predict the products of the

4. reactions you performed.

5. Are these reactions stereoselective, stereopsecific or do they give mixtures?

Part A O. 3 1.24 l 48