Exam 1

1. (15 points) Write complete names for each of the following.

a)

b)

c)

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2. (15 points) Write accurate structures for the following:

a) the best Lewis structure for H2CN2 ( C-N-N is linear )

b) two good resonance forms for the SCN anion ( S-C-N is linear )

c) the most stable chair conformation of trans-1,2-dimethylcyclohexane

d) a bicyclo[2.2.1]heptane that has a quaternary carbon atom (substituents are allowed)

e) the isomer of C6H14 that has ONLY primary and tertiary carbons

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3a. (12 points) Write structures and names for all the possible isomers of C3H6Cl2 .

3b. (12 points) Write structures and names for all the possible isomers of
dichlorocyclopropane.

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4. (15 points) Write Newman diagrams for all three staggered conformations of
3-bromo-2-methylpentane. Carbon-1 is shown on the first diagram to get you started.

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5. (16 points) Complete the following acid-base reactions and predict whether the equilibrium will be favored to the right or to the left.

a)

b)

c)

d)

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6. (15 points) Shown below is a chair conformation and a Newman diagram of the same structure.
Carbons 1 and 3 are identified on each to help orient the two views.
Place the following substituents at the indicated locations on each of the two structures:

Write the other chair conformation of this same compound (with all four substituents) in both a Newman and a chair structure.