CHEM1280 Midterm Exam (2011)

Section 1 (60 points totally)

1. Name the following molecules with the systematic nomenclature using the R/S system for
the asymmetric centers and the E/Z system for alkenes. (6 points)

2. Draw the following structures. (9 points)

(a) skeletal structure of toluene (b) Newman projection for the most stable
conformation of 3-ethyl-pentane, considering
rotation about the C-2—C-3 bond.
(c) skeletal structure for the most stable (d) Fischer projection of the meso stereoisomer
chair conformer of trans-1-ethyl-4- of 2,3-dichlorobutane
methylcyclohexane

3. Rank each of the following groups of molecules. (12 points)

(a) Rank the following compounds in order of decreasing reactivity toward electrophilic
aromatic substitution.

(b) Rank the following alkenes in order of increasing reactivity toward the electrophilic
addition of HBr.

(c) Rank the following bases in order of decreasing strength.

(d) Rank the following structures in order of decreasing stability.

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4. Draw structures a-f showing stereochemistry if necessary. (14 points)

5. (a) Sulfoxide A exists as a pair of stereoisomers. What type of stereoisomers are they?
Draw structures of the two stereoisomers of A.
(b) Azo compound B also exists as a pair of stereoisomers. What type of stereoisomers
are they? Draw structures of the two stereoisomers of B. (8 points)

6. Following are eight stereo-representations of 2,3-butanediol. Among B to G, which are

identical to A, which are the enantiomer of A and which are the diastereomer of A? (11
points)

Section 2. Choose Four questions from this section to answer. Please indicate which
question you want to be graded by circling the question number. If you choose five questions
from this section, the fifth one will not be graded. (40 points totally)

7. Propose a reasonable mechanism for the following reaction using the curved arrows to
show the flow of electrons. (10 points)

8. Propose a reasonable mechanism for the following reaction using the curved arrows to
show the flow of electrons. Explain why the product is not 1-chloro-2-iodo-2-
methylpropane. (10 points)

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9. Calicene has an unusually large dipole moment for a hydrocarbon as shown below.
Explain the large dipole moment. (10 points)

10. Propose a reasonable mechanism for the following reaction using the curved arrows to
show the flow of electrons. Explain why the two tert-butyl groups are ortho to the -OH
group in the product. (10 points)

11. Draw products of the following two reactions showing stereochemistry if necessary.
Explain why the products of both reactions are optically inactive.