Chemistry 2262 Organic Chemistry II

Dr. Spivak
Spring 2015
Supplemental Instruction
Anthony Domma

What is Supplemental Instruction?

Supplemental Instruction (SI) is a program set up at LSU by the Center for Academic Success that helps
students pass courses that have high drop/fail percentages. The major way that SI helps students is by holding
SI sessions. These sessions are led by an SI instructor who provide a fun study environment for students to peer
teach each other in various ways. This philosophy of students teaching each other has proven to help students
significantly with raising their GPA and learning the material to pass the class. Organic Chemistry II is one of
the classes that has an SI offered at LSU. The following is the portfolio of the SI instructor Anthony Domma
which provides his approach to the spring of 2015 SI semester. All worksheets are on LSU CAS drive.
Before the Semester:
Students in Organic II sometimes forget the basic, fundamental concepts behind Organic I over the break
between semesters. To refresh the students on the material, I provided a Session 0 Organic I Review. This goes
over the essential reactions from Organic I that carry over into Organic II like Sn1, Sn2, E1, E2 and addition
reactions. I instructed the students to work on the worksheet in groups to correspond to the SI model and posted
an answer key so they could check the work when they were done. A sample from the worksheet is below:

Substitution Reactions

SN2 General Mechanism: the slow step of the reaction is dependent upon 2 molecules (bimolecular).

Draw the mechanisms for the reactions: (Include lone pairs, formal charges, arrows, and transition states)

SN1 General Mechanism: the slow step of the reaction depends upon the rate of one molecule (unimolecular).

*Dont forget about carbocation rearrangements!

Finish the mechanisms for the reaction: The first step is given (Include lone pairs, formal charges, arrows,
and transition states)

During the Semester:

Once the semester got started we went through the regular process of going to class, making SI worksheets and
lesson plans and performing exam reviews. The exams included tests on:
1. Aromaticity and Electrophilic Aromatic Substitution
reactions
2. Carbonyl Chemistry
3. Carboxylic Acids and their Derivatives
4. Conjugate Addition
5. Carbohydrate Chemistry and Phenol
The lesson plans were made by what I believed to be the best approach to studying the material. This varied
each session to what the material was on but included an assortment of graphs, charts, figures, synthesis,
reaction mechanisms, diagrams, reaction problems and stability labeling. A sample worksheet from each test is
posted below in the next pages. The sessions always tried to contain a spectroscopy problem, a synthesis, and
reactions because on every test there are these questions.
Making the worksheet:
The worksheets all corresponded to the SI model of having a warm
up activity (to review previous material or preview what will be on
the worksheet), 3-4 main activities (goes over the material that will
be on the test), and a closing activity (which ties in the material to
the overall picture and reiterates the material as a review). This
approach is a good way of making sure they are mentally
approaching the subject in the right mindset. The warm up will
focus the students on organic and brings the material down to a
level they can understand. The main activity will be the primary
mechanism of understanding. And the cool down reiterates the
material to ensure they learned something before leaving.
The problems in the worksheets not only went over the material
but also made the students think. If you look back at the examples
you will see many different charts that the students were never
exposed to in the notes. They have to look at the notes in a
different view to twist the answer into those charts. At the end of
the session the students knew the material better and had an
organized approach to the material.
The main activities were very successful in how it prepared the students for the tests because the ones I made up
were significantly harder than the ones on the test. For the students who were doing well, this challenged them
to do even better and for the student struggling it gave them an opportunity to learn from the students doing well
how do approach the questions. Sometimes the students did not understand it enough to attempt the question
and guidance was needed from me. I would provide an intermediate step or idea that got them through it. The
worksheet always had a logical flow throughout it to prevent jumping from subject matter to subject matter.

1. Aromaticity and Electrophilic Aromatic Substitution Test

Warm up:
Fill in the flowchart to satisfy the conditions of aromaticity.

No
Is the molecule cyclic?

Yes
Is the molecule
conjugated?

No

Yes

Is the molecule
planar?

No

Yes

How many pi
electrons does the
molecule have?

4n+2 pi electrons

4n pi electrons

Main Activity 1:
Fulfilling all the conditions of aromaticity provides a ton of stability for the molecule! Draw the P orbitals of the
following molecule to see how this stability can be physically seen.

Main Activity 2:
Find the structure of the following HNMR.

Main Activity 2:
Classify each of the following as aromatic, anti-aromatic or non-aromatic and explain why it falls under that
classification.

Main Activity 3:
Draw the general mechanism for electrophilic aromatic substitution of benzene. Make sure to include all
structures, electrons, curved arrows, formal charges and resonance structures

Wrap-up Activity:
Aromaticity is an important way of stabilization in chemistry that can affect acid/base properties in compounds.
In the following molecules, when placed under acidic conditions, only one of the nitrogens will be protonated.
Circle the nitrogen that will be protonated and give explanation as to why it is protonated.

2. Carbonyl Chemistry Test

Warm Up:
1. List the following in order of reactivity of the carbonyl carbon. (Credit Paul on this question)

2. Label the following as Acetals, Hemiacetals, Ketals or Hemiketals.

Main Activity 1:
Draw a complete arrow pushing mechanism for the following reaction. You can use whatever reagents you
want just be sure to draw all the resonance structures, free electron pairs and formal charges.

Main Activity 2:
For the following molecule draw the product you would get using the reagents that are listed in the chart on the
molecule shown.

-OH
Acid
and
water

Base
and
water

-OR

-CN

Main Activity 3:
Reactions: Give the product of the following reactions.

Main Activity 4:
Synthesis

Closing Activity: For the following chart, fill in the missing reagents.

HNMR:
In groups, give the structure of the following compound. And do the ABC thing you did on the test.
Molecular structure: C5H12O
6H

3H
1H

2H

3. Carboxylic Acids and their Derivatives Test

Warm up:
1.) List the following in order of decreasing reactivity. So put them in order of most reactive to least reactive. If
they have the same general reactivity you can put a box around them and give them all the same number.

2.) Short Answer:

Explain how basicity of the leaving group correlates to the reactivity of the carbonyl.

3.) Chart:
1) Fill in the >,<, or ~ of the chart graph thingy below. 2) Draw arrows showing which products you can get
from which starting molecule. (Ill explain if youre confused)

Main Activity 1: Fill out the products below:

X = Something that is less basic than Y

Y = Something that is more basic than X

Mechanism:
Draw an arrow pushing mechanism for the reactions that yield products.
1.)

2.)

Main Activity 2: Exceptions to the rule:

1.)

Explain why this is an exception and why the chemistry still works.

2.)

Explain why this is an exception and why the chemistry still works.

3.)

Draw the mechanism of the following reaction.

4.)

Explain why this is an exception and why the chemistry still works.

Closing Activity:
Fill in the reactions below by either giving the product or the reactants of the following reactions. If a particular
reaction is not possible, put no reaction.

Bonus:
Compare and contrast nucleophilic carbonyl substitution with nucleophilic carbonyl addition.
Addition
Both
Substitution

4. Conjugate Addition Test

Warm Up:
1.)

2.)

Draw a complete arrow pushing mechanism for the acid and base tautomerism of the previous molecules.

Main Activity II:

Give the products of the following reactions:

Main Activity III:

Describe the differences between the Kinetic and Thermodynamic product.

Main Activity IV:

Closing Activity:
Synthesis.

5. Carbohydrate Chemistry and Phenol Test

Warm Up: Fill in the empty boxes

Main Activity I: Obscure reactions

Memorize the following reactions:

Main Activity II:

Draw a complete arrow pushing mechanism for the following reaction.

Main Activity II:

Without your notes fill in the following chart.

Main Activity III: Synthesis

The Josh Game:

Best SI Sessions:
The best SI sessions of the year were the Aromaticity and the Electrophilic Aromatic Substitution session
(provided as example worksheet 1) and Carboxylic acids and their derivatives session (provided as example
worksheet 3). These two sessions had a very logical flow from working off of basic principles of chemistry.
Aromaticity session:
The session started off with a full proof way to determine Huckels aromaticity, anti-aromaticity and nonaromaticity by a flow chart. The students then discussed the importance of these characterizations of molecules
and drew out the stabilizing effects of the three categories. This activity also showed that the electrons that are
counted for Huckles Rule have to be in the aromatic system. The students then practiced in groups on examples
using the flow chart provided. The examples given provided various ways of looking at the electrons in the
system. In many examples the orbitals that were gone over in the previous example were needed to recognize
the aromaticity. Then we previewed the next session that went over EAS reactions and ended on a trick question
that most people got because they had the proper approach to the session. Again these aromatics were
significantly harder than what was on the test, but because the students explained it to one another and had the
ability to explain why these molecules were aromatic, they got all the questions on the test with ease.
Carboxylic acids and their derivatives session:
Electrophilic carbonyl substitution is a confusing subject to a lot of students because they do not understand the
basic chemistry that is prerequisite to the concepts. I made a YouTube video to explain that concept (see next
session). The session was successful because we used that video to truly understand the material. The warm up
took the information from that video and used it to understand reactivity of carbonyls. I paired students who
watched the video with students that did not watch the video so students who watched it could explain it to
students who didnt. Then I made everyone explain why that reactivity was the case to ensure the people who
did not watch the video understood the concept. Now that they understood the basic concepts, they went over
the reaction itself and the mechanism of the two ways it can go. They then practiced these reactions in groups
with some exam like questions. There are some deceptive exceptions to this basic reaction that looks like it
breaks rules but actually does correspond to the basic chemistry. We went over each exception and explained
why it corresponds to basic chemistry. Then to wrap up the session we went over all the examples of ECS.
YouTube Videos
Students at LSU do not know the chemistry of acids and bases very well so I made a video going over the
necessary information needed to understand the chapter of carboxylic acid derivatives. Carboxylic acids and
their derivatives are very much rooted in acid base chemistry. I felt a YouTube video was the easiest way to go
over the information and get it to the students.
Exam Reviews
There were exam reviews the day before each exam to ensure the students knew the material and had any last
minute questions clarified. These reviews were even more systematic than regular SI session, but they had a lot
of overlap in the questions. The exam reviews had the hardest questions to really challenge the students. These
exam reviews still had synthesis, reactions

Office Hours:
Office Hours are a great way to give individual attention to students. I always had office hours at a regularly
scheduled time but if a student could not make it to that time, then we would find a time to schedule an
appointment. I could work with the students though a problem they struggled with, go through the notes if they
dont understand a concept or topic or help them with homework.
Blooms Taxonomy:
Organic chemistry is very picture oriented but I often put short
answer questions that made them explain why that answer was
the answer. Almost no teacher or other SI makes the students
write paragraphs but I find that it is extremely helpful in going
that next step to understand the material. This corresponds to the
Blooms Taxonomy that was learned in training. Applying
knowledge by answering these questions is a solid way of
learning material but if a student analyzes and evaluates the
answer then they can have a higher level of mastery of the
material. Getting them to explain why and other approaches like
making them make their own questions is the highest goal of SI.
SI effecting studies:
SI does take up a good bit of time so I needed to stay ontop of my studies. Naturally people want to help others
before they help themselves so academics took a backseat several times this semester. But I learned a way to be
successful with my academics and be a successful SI. Several times it expandended my knowledge of a
particular subject and taught me things that I will learn later in other classes. For example, I will be taking a
Physical Organic Chemistry Class next semester and in my conversations with my professor he explained things
I will learn in that class. Being an SI has helped me with my academics more than hurt.

Outside Activities:
Worksheets are not the only thing that was done in the session because I did not want to bore the students with a
rhythmic schedule. Periodically, there were games performed that gave a little spice to the semester. These
games are listed below:
1. Chemistry Cup- This was a game I came up with in the shower before the semester. I tried to find an
experience that people did not want to do but made games that made it fun (like what the CAS tries to
do for studying). I came up with a spin-off of the drinking game Flip Cup. I gave each student a red solo
cup and divided them into 2 teams. I lined the 2 teams in groups and gave them a mechanism problem.
Mechanism problems are stepwise so each student would perform one step on the mechanism and flip
the cup off the side of the table. Once the cup lands
upright the next person on the team can perform the
next step in the mechanism. The team to finish first
wins. If a student did not know a step to the
mechanism, then another student could help. We
played this about 4 times throughout the semester.
2. The Josh Game- This game was introduced at training by my friend Josh Edwards and I adapted it for
Chemistry 2262. I put questions like empty
charts, synthesis questions, reactions and
empty diagrams on individual slips of paper. I
made two piles of questions and divided the
students into 2 teams. The students had to get
up from their group and get 1 question. They
would solve it as a group and help each other.
After the question was finished, they showed
me the answer and I either sent them back to
fix it or gave them the next question. The first
team to finish all the questions first wins. An
example problem can be found after the
example sessions.
3. Double Blind Name Game- In organic chemistry, the molecules that are being built are quite
complicated and correspondingly have complicated names. I tweaked a game from training 2 years ago
to help students practice names. The way this game works is that students get in pairs and sit back to
back from each other. I gave one person a molecule I built with a molecular model kit and the other the
proper elements and bonds to build that molecule. The person with the molecule has to develop the
name from the structure given and say that name to their partner. Once the person has the name, the
person has to build that molecule from the name. The molecular model make it easier to see than a
molecule on a piece of paper.

Tips for Success:

1. Be Prepared Not only is this a great Lion King
song but also a great approach to SI sessions.
Make sure the worksheet has a flow and that it
helps the student truly understand the material.
This tip is pretty much what all the portfolio has
said up to this point.
2. Learn names This tip is really about being
personable with the students. Listen to them when
they talk. Dont always talk about just organic but
joke around and have fun. I have a lot of students say that it is sometimes awkward going to SI sessions
in other subjects because the SI leader is not approachable. They feel like they cant ask questions and
they are almost scared to go. If you can establish a connection and relationship with them, it will make
them excited about the subject and ready to learn.
3. Incorporate jokes- At the beginning of the session
especially exam reviews I would tell organic jokes to
relax them and let them have some fun. The jokes all
pertained to the material and were just really nerdy.
Occasionally I would have activities were the students
would have to explain the joke or something. To the
left is a way that can help the students learn the ortho,
meta and para positions on a benzene ring. The
answers are: metabolic, orthodox, parafilm,
orthopedic, metaphase, paramedic, metaphor and
Mercedes benzene. These are ways that you can get
students smiling (or at least smirking) at school. I
wrote a song that parodied Im on a Boat for their
final exam review.
4. Know the material- Make sure you know what the material is and how to explain it if you need to. If you
dont know the material then the students will be deterred from coming to another session because it
wastes their time. Also if a student asks a question you dont know the answer to then say I dont
know. Do not make up something because that will result in confusion and distrust.
5. Take advantage of CAS This program can flourish if you take advantage of the things the CAS
provides to you. Take advantage of the CAS inventory. If you give out prizes, like CAS shirts, when
they win a game you can maximize the efficiency of learning. Take advantage of the SI drive where
others have posted their worksheets before. This can cut down the extreme workload you will have first
semester and get ideas about the session and worksheets. Take advantage of the crew of smart people
that come into the office every day. You will get ideas, learn things and make lasting friendships with
very fun people.

Final Reflections:
The SI year went as well as expected. There were a few bumps in the road from lack of communication with the
students as a result of me not communicating well with the professor. As an SI, one of my jobs is to be a
interceder between the students and the professor. I did not do a great job communicating with the professor and
if I would have done that I could have concentrated the efficiency of the session. Communication with the
professor is the area I need most improvement.