CHEM 2425 Lab Review for Lab final Spring 2017

This review is meant as a guide to help in preparing for the Lab final and should NOT be used as the sole
preparation for the lab final. For each experiment in the lab manual, it will help if the footnotes are reviewed.
Make sure you know the overall procedure for each experiment. Know how to do the calculations (Theoretical yield,
Percent yield etc)
1. Organic Spectroscopy
You should be able to come up with the structure of an unknown compound given the information from Mass Spec, IR
and/or NMR spectrum

2. Nitration of Methyl benzoate

What is Electrophilic Aromatic Substitution? Its Mechanism? Directing effect of substituents? Do the substituents on
the aromatic ring influence the rate of the EAS?
What electrophile was used? How was it generated? What products expected?

3. Diels Alder
Know the mechanism of the Diels Alder reaction
What diene and dienophile were used in this reaction?
What was the product isolated after week 1? Week 2?
How did you convert the intermediate to the final Diels Alder product?

4. Heme Analog
How was TPP prepared? How was TPP converted to the metal complex?
Why were TPP and the metal complex colored?
Do you expect TPP to be aromatic?
Did max change when the TPP was complexed with the metal? Why?

5. Aldol Reaction
What is an Aldol reaction? Its mechanism? Reactivity of aldehydes versus ketones?
Aldol addition versus condensation?

6. Multi Step synthesis Step 1: Synthesis of Benzoin from Benzaldehyde

What reaction is taking place? Role of thiamine? Solvent for recrystallization? Appearance of product?

7. Multi Step synthesis Step 2: Oxidation of Benzoin to Benzil

Reagent used? Any by product? How was the crude benzil recrystallized? Appearance of product?

8. Multi Step synthesis Step 3: Synthesis of tetraphenylcyclopentadienone

Why was product colored? What is the reaction taking place in this step?

9. OFF an insect repellent

Role of SOCl2, NaOH and HCl in the experiment.
Appearance of product?
Role of Sodium sulfate