Chem 213 Final Exam Signature:

Question 1
A: For the following molecules or ions, indicate whether they are (A) aromatic, (B) anti-aromatic,
or (C) not aromatic (assuming that all of the rings are planar).

B. Classify the following pericyclic reactions.

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Question 2
Consider the following amines.

Which amine is the most basic?

(briefly rationalize your answer)

Which amine is the least basic?

(briefly rationalize your answer)

Question 3
Using one of the three pairs of arrows A and B, shown below, indicate the position of the
equilibrium of each of the reversible reactions shown below. Circle the correct letter.

A)

A)
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Question 4. Cyclopentadiene is more reactive in Diels-Alder reactions than 2,4-hexadiene.

Provide a rationale for this observation.

Question 5. The following pericyclic reaction is the final step in the biosynthesis of vitamin D.

A. Classify the pericyclic reaction.

B. Will this reaction proceed thermally? In your answer, you can just analyze the top face of the
pi-system, as we did in class (i.e. suprafacial mode of reactivity). Please use MO diagrams in your
answer.
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Question 6. Supply the requested information. Be sure to indicate important stereochemical

details when appropriate. If more than 1 step is required, please label the different steps with (1),
(2), etc. You do not need to include the work-up in your answer.

A.

B.

C.

D.
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Question 7. Draw the structure of the products in the corresponding boxes. You can assume that
a workup step is present after each transformation.

A.

B.

C.

Major product
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Question 8. Using the curved arrow formalism, please supply a mechanism for each of the
following chemical reactions. You can write PT or tautomerize, where appropriate. Note:
incorrect use of these abbreviations will result in a mark deduction.
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Question 9. Using the curved arrow formalism, please supply a mechanism for each of the
following chemical reactions. You can write PT or tautomerize, where appropriate. Note:
incorrect use of these abbreviations will result in a mark deduction.
Chem 213 Final Exam Signature:

Question 10. Using the curved arrow formalism, please supply a mechanism for each of the
following chemical reactions. You can write PT or tautomerize, where appropriate. Note:
incorrect use of these abbreviations will result in a mark deduction.
Chem 213 Final Exam Signature:

Question 11. Using the curved arrow formalism, please supply a mechanism for each of the
following chemical reactions. You can write PT or tautomerize, where appropriate. Note:
incorrect use of these abbreviations will result in a mark deduction.
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Question 12. Using only the indicated compounds as the organic starting materials along with
any necessary solvents and reagents, indicate how the compound on the right can be prepared
effectively in the laboratory.
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Question 13.
Using only the indicated starting materials as the organic starting materials along with any
necessary solvents and reagents, indicate how each of the targets can be synthesized.

Starting Materials

Synthesize 2 of the following Targets