CHEM 2380: Exam Two Review
1. For the following reactions, suggest reagents that would accomplish the following
transformation. Why did you choose the one you chose? How would this be
different if it were a primary alcohol?
OH
O
?
2. Jones reagent will fail to give a positive test (color change) with what structure?
(circle ALL that apply)
a)
b)
c)
d)
e)
3. The final product, D, in the following reaction sequence would be:
4. Draw the molecular diagram of the following structure.
How many pi orbitals are present in the molecule below?
How many pi electrons are present in the system?
How many electrons in the non-bonding orbital?
How many in the HOMO?
How many in the LUMO?
5. Draw the mechanism of each of the following reactions. Label the kinetic product
and thermodynamic product.
6. Classify each structure as having pi bonds that are cumulated, conjugated, or
isolated. Explain your classifications.
7. For the following Diels-Alder reaction:
Draw the reaction mechanism
Predict the product of the following reaction (include stereochemistry)
Indicate that whether the substituents are donating or withdrawing, by
resonance or induction
Draw a diene that would be incapable of taking part in a Diels-Alder reaction
8. Retrosynthesis problem! What is the diene and dienophile you would use for this
molecule? How do you know? (Hint: Identify the first six carbons, then look
for the electron donating or withdrawing groups.)
9. Draw 1-methoxy-3-nitrobenzene. Provide a common name of the structure.
10. What are the parent names for substituted benzene rings you need to know?
11. Fill in the boxes below with the appropriate structures/reagents. Remember that
the bolded, hollow arrows () are retrosynthesis, and the normal reaction arrows
are the forward reaction) .
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