Experiment 7: Dihydroxylation of Cyclohexene and TLC Analysis Introduction The purpose of this experiment is to observe the formation of diol through two different reactions that are carried out with microscale techniques. It is to distinguish between stereoisomers, which means structures that differ in the spatial arrangement of atoms. The obtained products are then analyzed through TLC analysis to determine which stereoisomer of 1,2-cyclohexanediol is trans or cis compounds. Further on, this reveals how structure with same molecular formula can result in different properties due to the different arrangement of atoms in space. There are two reactions in this experiment and both begin with same material: cyclohexene. One is carried out …show more content…
Observations Action Observed Change Oxone is added to cyclohexene in Acetone White precipitate is formed Cyclohexene/ tert-butanol is added to KMnO4 Purple coloured mixture at first then brown with clusters TLC plate that has samples with Anisaldehyde and heat Plate turned yellow and then red with spots turning purple Table 3. Spectroscopic data Rf: Distance traveled by substance (center of spot)/ Distance traveled by solvent 1(standard Cis) Rf: 2.62/5.5: 0.48 2 (standard Trans) Rf: 2.21/ 5.5: 0.40 3 (co-spot standard cis and trans) Rf: 2.50/5.5: 0.45 4 (Oxone reaction mixture) Rf: 2.30/5.5: 0.42 5 (KMnO4 reaction mixture) Rf: 2.72/5.5: …show more content…
On the TLC analysis, lane 4 was almost similar to lane 2 (standard trans was run on this lane) and lane 5 was really close to lane 3 and lane 1 (standard cis was run on this lane). This was easy to know due to the similar Rf values. The Rf value also implied differences in the polarity between the stereoisomers. The cis compound in lane 1 and 3 were higher than that of the trans compound (lane 2, and 4). This explains that the trans compound is slightly more polar than the cis