CHM2123 – 2022 – Laboratory Report
A study in pink & blue: Investigating the dihydroxylation mechanism
of a cyclic alkene
Student(s) Name(s) Asha Doughty
and Number(s) : 300226452
This report is: Individual
Date: October 13, 2022
Teaching Assistant: Samuel Delisle
Weekly Lab Period Thursday
COMMENTS
• Your report is submitted electronically via Brightspace into the dedicated folder.
• This report can be completed individually or in pairs, with your assigned lab partner, to each student’s
preference. If done in pairs, each student must submit an identical copy of the report. Make sure to include
both your names and student numbers above. Both students will receive the same marks and comments.
• This lab report is due on the week of October 10th 2022, by the beginning of your respective lab section.
Do not trust Brightspace’s due date: since every student shares the same Brightspace page, the due date
found online is for the last section of the week.
• Your results and discussion will cover both reactions done for this experiment. Type all the answers using
Arial font, size 12 pt, directly in the cells provided. The cells are representative of the length of the expected
answer, and their sizes have been locked to discourage superfluously long answers. Anything exceeding
this expected length may be ignored by the TA.
• Molecular figures must be drawn using ChemDraw.
• Late penalty is 20%/day, starting the moment the report is due and going up every 24h.
Point distribution
Introduction and Experimental Section /5
Results and Observations /6
Discussion /36
Post-Lab Question /20
Conclusion /4
Appendix /1
TOTAL /72
, Introduction and Experimental Section
Explain briefly, and in your words, the objectives of this experiment, along with a quick description
of the reactions at hand and the method employed to achieve this objective. (5 pts)
In this experiment, there were two types of dihydroxylations (permanganate-based and oxone-
based), each with three possible mechanisms. The goal of this experiment was to determine
which of the three mechanisms best explains the reaction occurring for each type. Each
mechanism produces a stereochemical different product(s). The first mechanism for a
permanganate-based reaction produces only cis products. The second produces a mix of cis
and trans products, and finally the third produces only trans products. Similarly, for the oxone-
based reaction, mechanism 4 produces only cis products, 5 cis and trans products, and 6 only
trans products. Therefore, by isolating the final product and identifying its stereochemistry, the
type of mechanism is revealed. This was done by first reacting the cyclohexane and
permanganate or oxone. A quick vacuum filtration of the product filtered out any solid, leaving
only a pure liquid product. This liquid product was further purified by doing a liquid liquid
extraction. In the end, the organic phase was drained, containing the final dihydroxyl. To check
the stereochemistry of the dihydroxyl, a TLC was performed before and after the liquid liquid
extraction. A TLC of the mixture was compared against samples of known cis and trans
cyclohexane to determine its stereochemistry.
A study in pink & blue: Investigating the dihydroxylation mechanism
of a cyclic alkene
Student(s) Name(s) Asha Doughty
and Number(s) : 300226452
This report is: Individual
Date: October 13, 2022
Teaching Assistant: Samuel Delisle
Weekly Lab Period Thursday
COMMENTS
• Your report is submitted electronically via Brightspace into the dedicated folder.
• This report can be completed individually or in pairs, with your assigned lab partner, to each student’s
preference. If done in pairs, each student must submit an identical copy of the report. Make sure to include
both your names and student numbers above. Both students will receive the same marks and comments.
• This lab report is due on the week of October 10th 2022, by the beginning of your respective lab section.
Do not trust Brightspace’s due date: since every student shares the same Brightspace page, the due date
found online is for the last section of the week.
• Your results and discussion will cover both reactions done for this experiment. Type all the answers using
Arial font, size 12 pt, directly in the cells provided. The cells are representative of the length of the expected
answer, and their sizes have been locked to discourage superfluously long answers. Anything exceeding
this expected length may be ignored by the TA.
• Molecular figures must be drawn using ChemDraw.
• Late penalty is 20%/day, starting the moment the report is due and going up every 24h.
Point distribution
Introduction and Experimental Section /5
Results and Observations /6
Discussion /36
Post-Lab Question /20
Conclusion /4
Appendix /1
TOTAL /72
, Introduction and Experimental Section
Explain briefly, and in your words, the objectives of this experiment, along with a quick description
of the reactions at hand and the method employed to achieve this objective. (5 pts)
In this experiment, there were two types of dihydroxylations (permanganate-based and oxone-
based), each with three possible mechanisms. The goal of this experiment was to determine
which of the three mechanisms best explains the reaction occurring for each type. Each
mechanism produces a stereochemical different product(s). The first mechanism for a
permanganate-based reaction produces only cis products. The second produces a mix of cis
and trans products, and finally the third produces only trans products. Similarly, for the oxone-
based reaction, mechanism 4 produces only cis products, 5 cis and trans products, and 6 only
trans products. Therefore, by isolating the final product and identifying its stereochemistry, the
type of mechanism is revealed. This was done by first reacting the cyclohexane and
permanganate or oxone. A quick vacuum filtration of the product filtered out any solid, leaving
only a pure liquid product. This liquid product was further purified by doing a liquid liquid
extraction. In the end, the organic phase was drained, containing the final dihydroxyl. To check
the stereochemistry of the dihydroxyl, a TLC was performed before and after the liquid liquid
extraction. A TLC of the mixture was compared against samples of known cis and trans
cyclohexane to determine its stereochemistry.
