First Year
CHM1321 Final Exam
Prep Workshop
Hosted by Daniel Nguyen & Kevin Huang
Meet the tutors
Daniel Nguyen Kevin Huang
3rd year Translational and 3rd year Translational and
Molecular Medicine Molecular Medicine
Table of contents
01 Structure 03 π Bonds and Reactivity
Molecular structure, bonding, π bonds and aromatic compounds as nucleophiles,
stereochemistry addition reactions, stereochemistry, electrophilic
aromatic substitution
02 Simple Reactivity 04 Lab techniques
Acids, bases, electrophilic π
bonds, reactions, mechanisms,
functional group transformations
01
Structure
Fundamentals of organic chemistry focusing on
molecular structure, bonding, and stereochemistry.
Molecular Structure
Identify whether the following molecules are aromatic, antiaromatic, or non-
aromatic:
a. c.
b. d.
Stereochemistry
On the structure below:
a) show the stereogenic center(s) by labelling them with a star (*)
b) determine the priorities of the substituents on each stereogenic center. For
compounds with more than one center, make sure you clearly indicate which
priorities refer to which center. (Redrawing the structure helps)
c) determine the configuration of each stereocenter
Stereochemistry
Clearly indicate the specific relationship between the following pairs of
molecules (structural isomers, conformers, enantiomers, diastereomers, etc.)
a.
b.
c.
02
Simple Reactivity
Exploring acids, bases, and electrophilic π bonds in
organic chemistry through reactions, mechanisms, and
functional group transformations.
Simple reactivity
On the structure below, either two of the oxygen atoms can react with
HCl.
Draw the two possible conjugate acids that can be formed from this reaction.
Underline the weakest acid. Justify your answer.
Simple reactivity
On the structure below, either two of the oxygen atoms can react with
HCl.
Predict the site of protonation on the original molecule and briefly explain
your choice.
Simple reactivity
For each of the following, provide the product or reagent as necessary.
Simple reactivity
Draw the products of each of the following based on the mechanistic arrows used
03
π Bonds and Reactivity
Understanding π bonds and aromatic compounds as
nucleophiles through addition reactions, stereochemistry, and
electrophilic aromatic substitution.
π Bonds and Reactivity
Consider the following reaction:
During the first part of the reaction, the active electrophile is formed according to the
equation below. Provide a mechanism for this transformation. Hint: Draw the Lewis
structure of HNO2 first.
π Bonds and Reactivity
Consider the following reaction:
Provide a mechanism for the substitution.
π Bonds and Reactivity
Consider the following reaction: Draw a reaction co-ordinate diagram
that shows the energy pathways for
the three reactions shown above
(assume the reactants and product
have equal energies).
π Bonds and Reactivity
Consider the following reaction: Which of the reactions is the fastest
and why?
π Bonds and Reactivity
Consider the following reaction co-ordinate diagram.
Identify the various species on the
diagram by adding the letter
identifying each of the structures.
π Bonds and Reactivity
Consider the following reaction co-ordinate diagram.
Which species does the first,
second, and third transition state
of the overall most resemble?
What kind of transition state is
this?
π Bonds and Reactivity
Consider the following reaction co-ordinate diagram.
What is the name of the
approximation used to reach the
conclusions for the second and
third transition states?
π Bonds and Reactivity
Consider the following reaction co-ordinate diagram.
Which step in the sequence is rate
determining and why?
π Bonds and Reactivity
Consider the following reaction.
What is the mechanism of the reaction?
π Bonds and Reactivity
Which of the following reactions will be faster and why?
π Bonds and Reactivity
Consider the following reaction:
Write a detailed mechanism for this transformation.
π Bonds and Reactivity
Consider the following reaction:
Provide a brief explanation for the location of the heteroatoms in the final product
(regiochemistry). A structure maybe helpful here.
π Bonds and Reactivity
Consider the following reaction:
Briefly account for the stereochemistry of the final product. A structure may be
helpful here.
π Bonds and Reactivity
For each of the following, provide the product or reagent as necessary.
π Bonds and Reactivity
For each of the following, provide the product or reagent as necessary.
π Bonds and Reactivity
For each of the following, provide the product or reagent as necessary.
π Bonds and Reactivity
For each of the following, provide the product or reagent as necessary.
π Bonds and Reactivity
The Gatterman-Koch reaction can be used to make aromatic aldehydes.
Draw 3 Lewis structures for CO (single, double, and triple bonds). Rank the structures
in order of increasing “quality” and briefly justify your choice.
π Bonds and Reactivity
The Gatterman-Koch reaction can be used to make aromatic aldehydes.
What is the mechanism of the Gatterman-Koch reaction?
π Bonds and Reactivity
Suggest a synthesis of the following from benzene. You may use any
additional reagents as necessary. Be sure to include a retrosynthesis.
π Bonds and Reactivity
During a Friedel-Crafts alkylation, the order in which the reagents are
mixed is important. Generally, these reactions are done by slowly adding
the alkylating agent to the aromatic component. What is the advantage
of mixing the ingredients in this order rather than slowly adding the
aromatic component to the alkylating agent?
04
Lab techniques
Lab techniques
In one of your experiments, you used a Grignard reaction to make a
carboxylic acid.
As part of this experiment, the following procedures were given:
1. When the Grignard reaction begins to slow down, place 10 g of crushed dry ice in a
150 mL beaker. Do not take time to weigh the dry ice. Use approximately the
amount in the beaker indicated by your instructor. The CO2 is in large excess and
will not affect your calculation of percent yield of benzoic acid product. Cover the
beaker with a watch glass.
2. When most of the magnesium has reacted and the ether boiling subsides, quickly
pour the contents of the tube into the beaker containing dry ice.
Lab techniques
In one of your experiments, you used a Grignard reaction to make a
carboxylic acid.
As part of this experiment, the following procedures were given:
3. Add a few milliliters of ether to the test tube and swirl to rinse. Add the rinse liquid
to the beaker.
4. Cover the beaker with the watch glass and allow it to stand until the next lab
period. During the interim, the excess dry ice will have sublimed.
5. Hydrolyze the Grignard addition product by slowly adding 30 mL of 6M HCl to the
beaker with the sublimed dry ice and reaction mixture. Stir the mixture with a glass
stirring rod. If there is excess magnesium present, it will react with the HCl to
evolve hydrogen gas.
Lab techniques
In one of your experiments, you used a Grignard reaction to make a
carboxylic acid.
As part of this experiment, the following procedures were given:
6. Add 30 mL of tert-butyl methyl ether (TBME) to the beaker. Stir the mixture. There
should now be two distinct liquid layers.
Lab techniques
In one of your experiments, you used a Grignard reaction to make a
carboxylic acid.
What is the structure of the organic compound present in the beaker at the end of step
4?
Lab techniques
In one of your experiments, you used a Grignard reaction to make a
carboxylic acid.
What happens when the 6M HCl is added in step 5 (give a mechanism)?
Lab techniques
In one of your experiments, you used a Grignard reaction to make a
carboxylic acid.
Use a flow chart to show what happens.
Thanks!
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