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Dr. Spivak
Spring 2015
Supplemental Instruction
Anthony Domma
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).
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.
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.) 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)
Mechanism:
Draw an arrow pushing mechanism for the reactions that yield products.
1.)
2.)
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.)
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
2.)
Draw a complete arrow pushing mechanism for the acid and base tautomerism of the previous molecules.
Closing Activity:
Synthesis.
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.
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.