CHY 254 – ORGANIC CHEMISTRY LABORATORY II

Spring 2025
CONTACT INFORMATION:
Dr. Natalie K. Machamer ([email protected])
Faculty in charge of the Organic Chemistry Laboratory
Aubert Hall 253, 207-581-1170
Lee Bickerstaff ([email protected])
Laboratory Supervisor and Teaching Associate
Aubert Hall 251, 207-581-1128

COURSE GOALS:
Organic Chemistry is an applied science that is best understood through laboratory work. However,
to quickly understand the central concepts at play within Organic Chemistry, lectures provide a faster
method of presentation. It would be ideal to learn all Organic Chemistry through laboratory
experiences. Unfortunately, time does not allow us this luxury. This laboratory course has been
designed to complement the topics covered in CHY251 and CHY252 and give you hands on
experience with the concepts presented in class.
To gain the full potential from your lab time you should be fully prepared. Read the experimental
procedure in full prior to each laboratory. It should be noted that this is a separate course from
lecture, with a separate grade and while every attempt will be made to coordinate lecture and
lab this is not a guarantee, and you may be required to read ahead in your textbook to prepare
for lab. Your Teaching Assistant (TA) will present a short pre-lab lecture, but you will be expected
to know the experimental procedure and come to lab with any clarification questions. This may mean
that you will have to look up supplemental information in your textbook or refer to techniques you
learned earlier in the semester or in CHY 251/253.
If you have a disability for which you may be requesting an accommodation, please contact Student
Accessibility Services, 121 East Annex, 207-581-2319, as early as possible in the semester. Students
who have already been approved for accommodations by SAS and have a current accommodation
letter should meet with Dr. Machamer privately as soon as possible.

STUDENT LEARNING OUTCOMES:

By the end of this course a successful student should be knowledgeable in the following:
1) Learn proper organic chemistry laboratory techniques.
2) Apply appropriate scientific language in the preparation of lab reports and a lab notebook.
3) Become familiar with correct laboratory safety practices and chemical waste disposal.
4) Learn compound characterization methods (IR and NMR spectroscopy).

INSTRUCTIONAL OBJECTIVES:
By applying the topics and skills covered in CHY251 and CHY252 students will be able to
understand, communicate, and apply their knowledge of organic chemistry in a laboratory setting.
This will allow them to converse with chemists, but also scientists in many other fields in both the
written and verbal form.
REQUIRED MATERIALS:
• Organic Chemistry II Laboratory Manual, 6th Edition (only sold at UMaine bookstore)
• Bound Composition Notebook
• Safety Glasses or Goggles; stamped with “Z87” on the temple earpiece

BRIGHTSPACE:
A Brightspace page will be maintained for this course. Course materials (syllabus, worksheets, and
course announcements) will be posted to the page. Your TA will ask you to submit most of your work
on Brightspace. All your grades will be recorded on Brightspace. Please contact Dr. Natalie
Machamer ASAP if you cannot see your grades or your TA has not posted your grades in a
couple of weeks. Please make sure you can access the course page!

ATTENDANCE:
Students must attend the lab section to which they are assigned. If more than 2 labs are missed,
excused or unexcused, you will receive an F in the course. In order for an absence to be excused, you
must contact your TA and the laboratory supervisor BEFORE lab – you cannot attend a different
section unless prior approval is granted. Sending an email after lab is not acceptable! Make-up labs
are not guaranteed and will depend on TA/room scheduling, safety considerations, etc. Unexcused
absences will result in a ZERO grade for that laboratory experiment.

If you are more than 20 minutes late to lab, you may not be permitted to complete the
experiment and will earn a ZERO grade for that laboratory. If you are late, you will be asked
to speak with the laboratory supervisor.

If you are pregnant or become pregnant during the semester, this may limit your ability to perform
experiments in the laboratory; please immediately discuss this matter with Dr. Natalie Machamer.

What happens when a student drops or withdraws from lecture?

Dropping Lecture during Add/Drop: If a student chooses to drop lecture during the add/drop period
of the semester he/she must also drop lab. No exceptions will be made.

Dropping Lecture after Add/Drop: If a student chooses to drop lecture after add/drop, but before the
deadline for the class to appear on their transcript, he/she must also drop lab. No exceptions will be
made.

Withdrawing from Lecture: If a student chooses to withdraw from lecture, they may stay in lab (with
permission) if he/she has: 1) completed 9 experiments and 2) an average of at least 70%. No
exceptions will be made.
GRADING:

Pre-Lab Notes --
As part of your preparation before coming to lab you should prepare notes outlining the plan for the
lab period in your lab notebook. Refer to your lab manual for more details on how to prepare this
section. You should use your lab manual and the corresponding video posted on Brightspace to help
you write your pre-lab.

Pre-Lab Quiz --
During the pre-lab lecture portion of every laboratory period, you will complete a quiz that pertains
to the current day’s experiment. The quiz will consist of a few questions and will be a combination
of multiple choice and short answer. These questions will cover the aspects of the experiment
presented in the lab manual, during the pre-lab talk by your TA, and in the lab videos (if applicable).
The questions will pertain to the objective, mechanism(s), experimental details, and safety
considerations of the experiment.

In-Lab Notes --
During the lab period take accurate notes of your actual procedure in your lab notebook. Make notes
of any deviations from the procedure given in the manual. Mention if this was useful or not. You
should also note any significant transformations during the experiment “then the reaction turned
pink.”, “long needles of crystals started to form” etc. Use your own words to best describe the
situation as it evolves. These notes will be checked by your TA at the end of lab and will be considered
your “ticket out the door.”

Lab Report --
After the lab you should write up a full report for the experiment. The lab report is due according to
attached schedule. Your TA will hand out a rubric at the beginning of each experiment and provide
detailed instructions on how to write a proper lab report. There are also “Lab Report Guidelines” in
your lab manual that should be used for reference.

Handout --
For some of the experiments you will be asked to complete a handout instead of a full lab report. The
handout will be worth 40 points (unless noted otherwise) and will guide you through the analysis of
your data. You will also be asked to answer specific questions about the experiment and how they
relate to your data.

Participation --
Your TA will evaluate participation during each lab period. It is important to note that you are not
expected to be perfect but should come to lab prepared. Your point total will be influenced by the
following factors: Attitude and Effort (ex. coming to lab prepared vs. trying to cut corners),
Cooperativeness/Safety (ex. remember to wear gloves vs. constantly reminded), TA Dependence (ex.
ask questions which were clearly stated in book/lab manual vs. clarification questions), and
Organization of Time and Space (ex. work efficiently vs. waste time and then not complete
experiment).
Late Policy --
*Pre-Lab Quiz – no late quizzes will be given.
*Pre-Lab Notes – must be completed in your lab notebook before the beginning of the lab.
You may not be permitted to start the experiment if the Pre-Lab is not completed. No late Pre-
Labs will be accepted.

[Note: Remember that pre-lab notes, written in your lab notebook, are due at the beginning of
the laboratory period. Pre-lab notes will be checked before the pre-lab lecture begins. If you
are late to lab and arrive after the lecture starts, no points will be awarded for the pre-lab
notes. Losing these points is the penalty for being late to lab.]

*Lab Report/Handout – 10 points for lab reports and 5 points for handouts will be deducted
for late submission within the first week after the due date and after one week the lab report
or handout will not be accepted. Note: You are only permitted to turn in 2 reports/handouts
late. After turning in 2 late reports/handouts, any other reports/handouts (that are late) will
earn a zero.
*In-Lab Notes – will not be accepted if late. Do not leave lab until your TA has checked your
laboratory notebook!

COURSE GRADING:
Pre-Lab quiz = 10
Pre-Lab notes = 5
In-Lab notes = 5
Lab Report/Handout = 80/40 (unless noted below)
Participation = 5 (unless noted below)
Total 105/65 points per lab

Check-In 10 points (participation)

Oxidation 105 points (pre-lab, quiz, participation, lab notes, lab report)
Sample Prep 25 points (participation + 20 point in-lab handout)
Reduction 65 points (pre-lab, quiz, participation, lab notes, handout)
Grignard 130 points (pre-lab (x2), quiz (x2), participation (x2), lab notes (x2), lab report)
Diels-Alder 105 points (pre-lab, quiz, participation, lab notes, lab report)
EAS 65 points (pre-lab, quiz, participation, lab notes, handout)
Classification 65 points (pre-lab, quiz, participation, lab notes, handout)
Wittig 105 points (pre-lab, quiz, participation, lab notes, lab report)
Nylon 65 points (pre-lab, quiz, participation, lab notes, handout)
Biodiesel 105 points (pre-lab, quiz, participation, lab notes, lab report)
Aldol 105 points (pre-lab, quiz, participation, lab notes, lab report)
Check-Out 10 points (participation)
Total 960 points
Your grade will be calculated as a fraction of the 960 points you obtain during the semester. The top
and bottom 3% of each grade range will be used to assign plus and minus grades, respectively.

Letter Grade Score Cutoff

A- 90%
B- 80%
C- 70%
D- 60%
F Below 60%

COURSE ETIQUETTE:
This course has a scary reputation, but with the right attitude and determination all of you are
capable of successfully completing it!
1) During class, focus on understanding the material. I know everyone gets distracted at
times, but do NOT text, check social media, or email - this is a waste of your time and
money and disrespectful to the TAs and other students. This also is a safety concern due
to the nature of this course and you may be asked to leave if your actions are deemed
unsafe.
2) Speak respectfully to your fellow students and TA. They will do the same in return. This
includes email communication.
3) All students are expected to honor the University of Maine Codes of Conduct and
Academic Honesty Statement.
Academic Honesty Statement: Academic honesty is very important. It is
dishonest to cheat on exams, to copy term papers, to submit papers written by another
person, or generated by software or systems without the explicit approval of the
instructor, to fake experimental results, or to copy or reword parts of books or articles
into your own papers without appropriately citing the source. Students committing or
aiding in any of these violations may be given failing grades for an assignment or for
an entire course, at the discretion of the instructor. In addition to any academic action
taken by an instructor, these violations are also subject to action under the University
of Maine Student Conduct Code. The maximum possible sanction under the student
conduct code is dismissal from the University. Please see the University of Maine
System’s Academic Integrity Policy listed in the Board Policy Manual as Policy 314
(*Date Issued: September 1, 2020): https://www.maine.edu/board-of-trustees/policy-
manual/section-314/

4) Work hard and have fun!

COURSE SCHEDULE DISCLAIMER (DISRUPTION CLAUSE):

In the event of an extended disruption of normal classroom activities (due to COVID-19 or other
long-term disruptions), the format for this course may be modified to enable its completion within its
programmed time frame. In that event, you will be provided an addendum to the syllabus that will
supersede this version.
OBSERVANCE OF RELIGIOUS HOLIDAYS/EVENTS:
The University of Maine recognizes that when students are observing significant religious holidays,
some may be unable to attend classes or labs, study, take tests, or work on other assignments. If they
provide adequate notice (at least one week and longer if at all possible), these students are allowed to
make up course requirements as long as this effort does not create an unreasonable burden upon the
instructor, department, or University. At the discretion of the instructor, such coursework could be
due before or after the examination or assignment. No adverse or prejudicial effects shall result to a
student’s grade for the examination, study, or course requirement on the day of religious observance.
The student shall not be marked absent from the class due to observing a significant religious holiday.
In the case of an internship or clinical, students should refer to the applicable policy in place by the
employer or site.

SEXUAL DISCRIMINATION REPORTING:

The University of Maine is committed to making campus a safe place for students. Because of this
commitment, if you tell a teacher about an experience of sexual assault, sexual harassment,
stalking, relationship abuse (dating violence and domestic violence), sexual misconduct or any
form of gender discrimination involving members of the campus, your teacher is required to
report this information to the campus Office of Sexual Assault & Violence Prevention or the Office
of Equal Opportunity.

If you want to talk in confidence to someone about an experience of sexual discrimination, please
contact these resources:

For confidential resources on campus: Counseling Center: 207-581-1392 or Cutler Health

Center: at 207-581-4000.
For confidential resources off campus: Rape Response Services: 1-800-310-0000 or Partners for
Peace: 1-800-863-9909.

Other resources: The resources listed below can offer support but may have to report the incident
to others who can help:

For support services on campus: Office of Sexual Assault & Violence Prevention: 207-581-1406,
Office of Community Standards: 207-581-1409, University of Maine Police: 207-581-4040 or
911. Or see the OSAVP website for a complete list of services at http://www.umaine.edu/osavp/
 CHY 254 – ORGANIC CHEMISTRY LABORATORY II
Spring Semester 2025 - Course Schedule
Assignment Due
**Unless otherwise noted,
Date – 2025 Topic Manual assignments are due at the
BEGINNING of your scheduled
lab**

Week of Jan. 21st Check-In; Safety; Procedures

Week of Jan. 28th Oxidation of 9-fluorenol pg. 45 - Pre-Lab (Oxidation)

- Lab Report (Oxidation)

Sample Preparation; IR and NMR
Week of Feb. 4th pg. 51 - In-Lab Handout
Spectroscopy
(IR/NMR)
Sodium Borohydride Reduction of - Pre-Lab
Week of Feb. 11th pg. 53
Vanillin (Reduction)
Generation and Reaction of an - Pre-Lab (Grignard)
Week of Feb. 18th pg. 63
Organometallic Compound (Part I) - Handout (Reduction)
Generation and Reaction of an - Pre-Lab
Week of Feb. 25th pg. 63
Organometallic Compound (Part II) (Grignard, Part II)
Diels-Alder Reaction of - Pre-Lab (Diels-Alder)
Week of Mar. 4th pg. 73
Cyclopentadiene - Lab Report (Grignard)

- Pre-Lab (EAS)
Week of Mar. 11th Electrophilic Aromatic Substitution pg. 83 - Lab Report
(Diels-Alder)

Week of Mar. 18th Spring Break!

Classification Tests for Aldehydes and - Pre-Lab (Classification)

Week of Mar. 25th pg. 91
Ketones - Handout (EAS)

- Pre-Lab (Wittig)
Week of Apr. 1st The Wittig Reaction pg. 101
- Handout (Classification)

- Pre-Lab (Nylon)
Week of Apr. 8th Nylon 6,6 Synthesis pg. 107
- Lab Report (Wittig)

- Pre-Lab (Biodiesel)
Week of Apr. 15th Synthesis of Biodiesel pg. 115
- Handout (Nylon)

- Prelab (Aldol)
Week of Apr. 22nd Solventless Aldol Condensation pg. 121
- Lab Report (Biodiesel)

Week of Apr. 29th Check-out; Clean-up - Lab Report (Aldol)