Practice Final Exam B

CHM 2210

This practice exam contains 6 pages (including this title page) and 150 points worth of
questions. It should take you no more than 2 hrs to complete it (90 minutes if you are well
prepared).

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CHM 2210 Practice Final Exam B

1. Follow the instructions below: 27 pts.

a. Provide the complete IUPAC name for the b. For the following reaction, indicate what
molecule shown below. (4 pts) happens to the reaction rate if the volume
of CH3OH and the amount of NaOCH3 are
doubled. (2 pts)

The reaction rate ____________________.

c. Rank the molecules below in terms of d. Rank the radicals below based on their
their acidity (least acidic to most acidic). stability (least stable to most stable).
(3 pts) (3 pts)

least acidic ___ < ___ < ___ most acidic least stable ___ < ___ < ___ most stable
e. For each nitrogen atom in the molecule shown below, indicate its hybridization and the
nitrogen’s lone pair orbital. Then indicate which nitrogen in the molecule is more basic.
(6 pts)
Nitrogen A is ___ hybridized and its lone pair resides in a/an ___ orbital.

Nitrogen B is ___ hybridized and its lone pair resides in a/an ___ orbital.

Nitrogen ___ is more basic.

f. Answer the following questions about the molecule shown below. (9 pts)

(1) Circle all chiral carbon atoms in the molecule above.

(2) Circle the 3° amide group in the molecule above.
(3) What is the hybridization of oxygen A?
(4) Which orbitals overlap to form the bond labeled B? (e.g. Csp–H1s)

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CHM 2210 Practice Final Exam B

2. For each of the pairs of molecules shown below, indicate their relationship as
conformational isomers, enantiomers, diastereomers, geometric isomers (cis/trans isomers),
constitutional (structural) isomers, identical or none. Choose the most specific answer that
you can: 18 pts.

a. b.

_________________________ _________________________
c. d.

_________________________ _________________________
e. f.

_________________________ _________________________

3. Draw all meso stereoisomers of the compound shown below (by using dashes and wedges).
You do not need to draw chair conformations. Note: you will be penalized for redundant or
irrelevant structures: 12 pts.

4. Draw the most stable (lowest energy) chair conformation of the molecule shown below.
Draw all substituents and all ring hydrogens. Only one structure, please: 6 pts.

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CHM 2210 Practice Final Exam B

5. Draw the expected products for the following reactions. Look carefully for helpful hints. Treat
each stereoisomer as a separate product and draw it. No mechanisms are required.
Note: you will be penalized for redundant or irrelevant structures: 45 pts.
a. (8 pts)

b. (6 pts)

major elimination product single major product

c. (10 pts)

d. (9 pts)

e. (6 pts)

f. (6 pts)

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CHM 2210 Practice Final Exam B

6. First, draw a detailed stepwise mechanism for the reaction below that explains how the
product shown is formed. Use the curved arrow formalism and do not leave out any steps.
Second, draw the structures of a possible tertiary alcohol substitution product and a
possible cycloalkane elimination product. A mechanism is not required for the alternative
products. You can ignore stereochemistry in this problem: 11 pts.

7. Draw a detailed stepwise mechanism for the reaction shown below. Use the curved arrow
formalism and do not leave out any steps. You can ignore stereochemistry: 9 pts.

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CHM 2210 Practice Final Exam B

8. Propose a synthesis for the targets shown below using the starting materials provided and
any other materials/reagents you need. Show all reagents/conditions that you would use in
each step. Draw out all synthetic intermediates that are stable enough to be isolated (no
cations, anions or radicals). No mechanisms: 22 pts.
a. You can ignore stereochemistry. (11 pts)

b. (11 pts)