CHM2123 – ORGANIC CHEMISTRY

LABORATORY II
FALL 2020 – Syllabus
Laboratory experiments to accompany CHM2120. (Synthesis and reactivity of
carbonyl compounds, organic acids and their derivatives, nitrogen-containing
compounds, sulfur derivatives, simple aromatic compounds. Survey of the chemistry of
carbohydrates, lipids, amino acids and peptides, and selected heterocycles.)

Instructor Dr. François Magnan

Office STM403
Email [email protected]
Email policy When contacting me, please indicate CHM2123 in the
subject line, and include your full name, student number,
TA’s name and lab section. (CC your TA, if applicable)
Emails will be answered chronologically, usually within one
business day.
For all questions regarding the experiments, please contact
your respective TA.
Office Hours Variable; see Brightspace for week-to week schedule.
Prerequisite CHM1321
Co-requisite CHM2120

COVID-19 Disclaimer

This syllabus assumes a full uninterrupted semester, where every student will have the
chance to perform every experiment, along with the practical examination. Of course
this can change at any moment, based on the situation.

A few details:
 The scheduling has been planned to allow for a bit of flexibility. In the case of
short disruptions, the weekly calendar will be modified to maximize lab
participation.
 In case of lab disruptions, online discussions and video material will be used
instead for the completion of pre-lab questionnaires and lab reports. Additional
exercises may be provided.
 In case the practical exam is cancelled, the weight will be shifted toward both
reports and the final written exam.
Evaluations

Pre-Lab Questionnaires 15%

Lab reports 25%
TA Evaluation 10%
Practical Exam 10–20%
Final Exam 30–40%

 You must obtain at least 50% in the practical components (reports + TA

Evaluation + Practical exam) in order to pass the course.
 There is no supplemental exam for this course, nor any extra-credit assignment.
 A student with three or more unexcused absences from the laboratory will
automatically receive a letter grade of E in the course.
 A penalty of 20% per day is applied for late submissions, applicable immediately
by the deadline.

Pre-Lab Questionnaires (15%)

As part of each pre-lab, you must fill a short pre-lab document, which will cover relevant
theory for the upcoming lab and ensure you are well prepared.
 The pre-lab document is due 48 hours later, before the beginning of your
corresponding lab session (except for the 1st experiment).
 Pre-lab questionnaires can be submitted either individually or in teams, to the
discretion of each student. All team work must necessarily be done with your
assigned lab partner.
Additionally, you must prepare the following in your lab notebook: a reaction scheme, a
table of reactants and solvents, necessary pre-lab calculations for quantities measured.
Your table of reactants should contain reactant/solvent name, molar mass, quantity,
density (if a pure liquid), number of moles and equivalents (equivalents are not required
for solvents). As you perform the experiment, you should note down relevant
observations and measurements in the lab notebook. This notebook preparation will
contribute toward your daily TA evaluation: this evaluation will be done individually.

Lab Reports (25%)

The lab experiments are performed in pairs. All lab reports can be submitted either
individually or in teams, to the discretion of each student. Again, team reports must
necessarily be done with your assigned lab partner.
 Lab reports are now in a worksheet-based format.
 Lab reports are due one week after the experiment is completed and must be
submitted prior to the start of your following lab session.
  Your reports and worksheets will be corrected following a detailed marking
scheme by your TA by the beginning of the following lab period.

TA Evaluation (10%)
Each student will be individually assessed by his/her respective TA over the course of
the laboratory periods. This evaluation will be based on punctuality, time-management
skills, preparedness, notebook upkeep, understanding of basic chemical concepts,
laboratory skills, cleanliness and politeness.

Practical Exam (10–20%)

The practical exam will take place during your regular lab period on the week of
November 30th. The practical exam will be 180 minutes long (including cleaning time),
performed independently and will include a short questionnaire. Further details will be
provided on Brightspace before the exam.

Final Exam (30–40%)

 A written final exam during the regular exam period in December will summarize
the key concepts, laboratory techniques and reactions studied in this course. The
exam is cumulative.
 A copy of the 2015 final exam will be made available on Brightspace to assist
you.
 Additional office hours and review sessions will be made available. Further
details will be posted on Brightspace.

Lab Scheduling

Each experiment is now slated to run over the course of two weeks. The first week will
be a one-hour long introductory session held online during your normally allocated
laboratory time slot: written and video content will be made available prior to the session
for you to get started on the experiment. The session will consist of a short recap of the
experiment, followed by a Q&A session. The second week will be a regular laboratory
session. Specific scheduling for the introductory sessions will be posted along the
semester.

Lab Documentation

 The experiments are posted on Brightspace. You are expected to print off the
documentation and to keep a binder of the necessary lab documents.
 Make sure to read the files posted in Supplementary Information, and be familiar
with the laboratory requirements.
  Video content has been developed to help the students in the laboratory. These
can be divided into two categories:
o Technical videos, which explain and demonstrate how to perform common
laboratory techniques.
o Experimental videos, which are specific to each experiment. They briefly
introduce relevant theory to the experiment, and include a video
demonstration of the upcoming experiment to familiarize students with
what they will have to do.
These videos are hosted on YouTube as part of the Dr. Frank’s Lab Bench: links to
these videos can be found on Brightspace.

Recommended Reading

New textbooks are expensive! Buying used, renting, or borrowing from the library are
also viable options
 Nichols, Organic Chemistry Laboratory Techniques, 2 nd Edition, 2017, pdf. on
Brightspace.
 Clayden, Greeves, Warren and Wothers, Organic Chemistry, 2nd Edition, 2012,
Oxford Press, 1260p.

Required Material

 Lab coat, safety glasses, long pants, closed shoes.

Lab coats, googles and nitrile gloves can be purchased from the SSA
office in STM203.
 Due to COVID-19, disposable paper masks are required at all times when in the
undergraduate laboratory. These will be provided to you at the beginning of each
lab.
 Bound notebook
 Lab notes
 Pen, pencil, ruler, permanent marker, USB drive
Due to the messy nature of the laboratory, exercise cautious judgement
when working on a laptop or tablet in the undergrad lab. Work in a clean
area away from a bench, and ALWAYS REMOVE your gloves.

Safety

Anyone showing blatant disregard for proper safety procedures will be asked to leave
the lab and will receive a grade of zero for that experiment.
 The following items must be properly worn at all times when in the lab (starting
at the official beginning of the class and right until you leave the room): a fully
 buttoned-up lab coat, safety glasses, disposable masks, closed-toed shoes that
completely cover your feet, and long pants.
 Students whose attire does not meet to the dress code will be asked to leave and
come back for a subsequent laboratory session, if available. Students that are
found to disregard the dress code during the lab session will automatically
receive a TA evaluation of 0 for the day.
 Headphones are not permitted in the laboratory: you need to be fully aware of
your surroundings in case of any issues.
 Long hair must be tied back.
 If you spill something on your hands, wash them immediately with cold water and
consult with your TA.
 TAs are required to give warnings and penalties to students who do not follow
safety rules. The penalty for the first warning will be at the discretion of the TA. A
second warning will result in expulsion from the lab. The experiment may not be
repeated at a later time.

 Waste disposal is a serious topic in a chemistry lab. Sinks are connected to the
city’s sewers, so it is imperative that you do not discard any chemicals in there.
Before washing glassware in the sink, you should equally rinse your glassware
thrice with water and discard into the solvent waste bins to prevent any
contamination.
 Similarly, any contaminated solid waste should be discarded in the appropriate
container rather than the garbage cans, which are disposed of as household
garbages. Any evidence of improper garbage disposal can result in a daily TA
evaluation of zero for the entire section.

Plagiarism

Submitting another person’s data, words, ideas, figures, ChemDraws, etc., within
lab reports and other works and passing them off as your own is considered plagiarism
unless otherwise cited. Secondly, the complete or partial translation, as well as
paraphrasing, of a text written by someone else also constitutes plagiarism if you do not
acknowledge the source.
If you decide to write a report alongside others, be certain to express yourself in your
own words and to present independent ideas. Any sign of plagiarism in a document will
result in a grade of zero for the entire work, and will be passed along to the coordinator.
You are strongly encouraged to review the University of Ottawa’s policy on plagiarism
and academic integrity, available at
 http://sass.uottawa.ca/sites/sass.uottawa.ca/files/plagiarism.pdf.
Schedule

Week Experiment
Sept. 14th–18th Meet and Greet
Experiment 1 – Introductory Session
Tools of the trade: Thin-Layer Chromatography and Liquid-Liquid
Extraction
Sept. 21st–25th Experiment 1 – Laboratory Session
Tools of the trade: Thin-Layer Chromatography and Liquid-Liquid
Extraction
Sept. 28th–Oct.2nd Experiment 2 – Introductory Session
A study in pink and blue: Investigating the dihydroxylation
mechanism of a cyclic alkene
Oct. 5th–9th Experiment 2 – Laboratory Session
A study in pink and blue: Investigating the dihydroxylation
mechanism of a cyclic alkene
Oct. 12th–16th Experiment 3 – Introductory Session
Competition studies between Substitution and Elimination
Reactions
Oct. 19th–23rd Experiment 3 – Laboratory Session
Competition studies between Substitution and Elimination
Reactions
Oct. 26th–30th Reading Week – No Lab.
Nov.2nd–6th Experiment 4 – Introductory Session
The reductive amination of vanillin
Nov.9th–13th Experiment 4 – Laboratory Session
The reductive amination of vanillin
Nov.16th–20th Experiment 5 – Introductory Session
Study of the reactivity of enolates
Nov.23rd–27th Experiment 5 – Laboratory Session
Study of the reactivity of enolates
Nov.30th–Dec.4th Practical Examination
Dec.7th–11th Review Sessions – Final Exam