CHEMISTRY 242 EXAM 1 - Practice

Tuesday, February 4, 2020 – 10:30 - 11:50 AM

Professor Amos B. Smith, III

NAME: _________________________________________________________________

Student ID: ______________________________________________________________

My signature below certifies that I have complied with the University of Pennsylvania’s
Code of Academic Integrity in completing this examination.

Signature: ___________________________ Date: ____________

CAREFULLY READ ALL QUESTIONS BEFORE ANSWERING THEM.

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1.

Provide structures for the major organic product(s) for the following reactions showing
stereochemistry where appropriate. If you predict that no reaction will take place, indicate “no
reaction”.

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(1 continued…)

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2.

a) Consider dienes 1, 2, and 3. Indicate the diene you expect to be the MOST and LEAST
reactive in a Diels Alder reaction.

b) Draw the molecular orbitals of the π-system of butadiene (1), placing the electrons in the
appropriate energy levels and labeling the HOMO and LUMO

c) Relative to the HOMO of butadiene (1), where would you place the respective energies of
those of (E)-1-methoxybutadiene (2) and (E)-1-cyanobutadiene (3)? Add the HOMO of
each into the drawing of 1

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3. One of the following hydrocarbons is much more acidic than the others. Indicate which one
(circle it) and explain its unusual property.

4. The following reaction can afford 2 structural isomers. Draw them both and write a
plausible mechanism accounting for their formation, paying particular attention to
stereochemistry. Give one reason supporting the preferential formation of each isomer.

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5. For each of the compounds below, indicate the number of π-electrons and whether they
are aromatic, anti-aromatic, or non-aromatic.

6. Provide either the diene or dienophiles for the following Diels Alder reactions

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