Question List for In-Class Presentations (CHEM 30CL)

After your presentation, you and your partner will each be asked a question from the list
attached. Some of these questions are taken directly from lecture content or pre-/post-lab
assignments. Some are more challenging and will require a bit of research and deduction.

To receive the highest credit possible, your answers should be thorough, specific, and
involve appropriate drawings (e.g. of resonance structures, mechanisms, equations applied) on
the board.

If you get stuck, keep in mind that you can always ask us for help!
Lab 1

1. (a) What was the purpose of using saturated ammonium chloride in the reaction workup?
(b) What was the purpose of using brine (saturated sodium chloride) in the reaction workup?

2. If imine hydrolysis occurred before the aldol addition step, what would the consequence be?

3. What is the approximate pKa of: (1) a protonated amine, and (2) a carboxylic acid? Given these pKa
values, calculate the Keq of the reaction below. What does this Keq value mean for the solubility of proline?

Keq?
O N O N
H H2
OH O
proline

4. Briefly explain the difference between an E1 and an E2 elimination (providing at least one example on the
board). Which elimination pathway is more likely in our reaction, and why?

5. Briefly explain the regioselectivity of the aldol addition step. Draw the structures of other possible aldol
addition products, and explain why they are not formed.

Lab 2

1. What was the purpose of using a “silica plug” (small silica column in a pipet) in the reaction workup? Be
specific about which species is filtered out, and why.

2. Briefly explain why the photoredox catalyst become a better oxidant and a better reductant upon
photoexcitation.

3. How many stereoisomers does the product of our reaction have? Draw all of them and indicate whether they
are diastereo- or enantiomers. Why is our isomer favored?

4. Indicate all positions that are deshielded by the nitro group by resonance in the compound below. Which
proton(s) would have the most downfield signal in this molecule?

NO2

5. If we were to use the compound below (which is an isomer of trans-anethole) for this reaction, what
modification to our catalyst would you propose, and why?

OMe
Lab 3

1. Explain why at least 1 equivalent of base (sodium acetate) is needed for this reaction.

2. What is the purpose of the Celite plug in the reaction workup? What would happen if a silica plug were
used instead?

3. What base would be required to deprotonate benzene if no C–H functionalization catalyst (e.g. [Cp*IrCl2]2)
is present? Give one example of such a base.

4. The imine starting material in this reaction is prone to imine hydrolysis. Provide the mechanism of the imine
hydrolysis, and state at least 3 ways to suppress this process.

5. We used N-benzylidenemethylamine for our C–H activation reaction. Would it be easier or harder to
perform our C–H activation reaction on the compound below? Briefly explain your reasoning.

Lab 4

1. Provide a mechanism for the decomposition of EDCI upon contact with water.

2. Amide protons usually show up around 6–7 ppm. Why does our amide proton show up around 12 ppm?
Why does our amide have a higher Rf value than the amine starting material?

3. The primary amine starting materials used in this reaction degrade over time in air due to reaction with
carbon dioxide. Provide a mechanism of this process.

4. Which one is a better base and nucleophile, DMAP or pyridine? Briefly explain your reasoning.

N
N
DMAP pyridine

5. Which one of the following 4 amines would be the best for an amide coupling reaction, and why?

H 2N
H 2N N
H 2N H
Lab 5

1. What is the role of copper in this reaction? (List at least 2, and be more specific than just saying that it’s the
catalyst.)

2. Using Hooke’s Law and drawing the relevant resonance structures, explain why the C=O stretching band
shows up at higher wavenumbers for esters than for amides.

3. For the triazole molecule below, draw all possible resonance structures for which all atoms have an octet.

N
N
N

4. Identify the most acidic proton in ascorbic acid, and briefly explain why it is the most acidic.

HO
OH

O
O OH
OH
ascorbic acid

5. The micelle-forming molecule we used not only enables us to run this reaction in water, but also accelerates
the reaction compared to using a conventional organic solvent. Briefly explain why.

Lab 6

1. Why does the metallocarbene proton signal shift upfield in the propagating polymer compared to the
Grubbs’ catalyst?

2. In polymer chemistry, “backbiting” refers to when a propagating polymer terminates itself by reacting
intramolecularly with one of its own C=C double bonds. Why is “backbiting” not a problem for our ROMP
reaction?

3. In the 1H NMR of the monomer, only one alkene proton signal is present. In the polymer product, 2 alkene
proton signals are present. Explain why.

4. Ring-closing metathesis (RCM) is another useful type of olefin metathesis reaction. What is the driving force
for RCM?

L nM

5. Provide the structure of the propagating polymer in the box.

Grubbs 1st
generation catalyst
Lab 7

1. Why is an excess (> 1 equivalent) of both the base and the phosphonium bromide used for this reaction?

2. (a) Would n-butyllithium (nBuLi) be an acceptable base for this reaction?

(b) Would tert-butyllithium (tBuLi) be an acceptable base for this reaction?

3. Our phosphonium ylide has to be generated in situ immediately before use due to its instability. Propose a
way to stabilize the phosphonium ylide structure.

4. Why is the phosphonium ylide intensely colored? Why does the color persist after the addition of water to
the reaction mixture?

5. Briefly explain why the E-alkene elutes before the Z-alkene on gas chromatography.