Problem Set #1

Chem 260

1.
HN

C
O

HN

O
N

What is the hybridization state of the following

atoms?

Name the circled functional groups.

2. Consider the conformations about the C4-C3 bond of the molecule shown below (view as
indicated by the arrow). Complete the Newman projections below using only staggered and
eclipsed conformations to indicate the order of stability of conformations about this bond (starting
with the most stable one and ending with the least stable one).

5
3

view

H3 C

H H3 C

CH(CH3)2
most stable

H3 C

H H3C

CH(CH3)2
2nd

H H3 C

CH(CH3)2
4th

CH(CH3)2
3rd

H H3C

CH(CH3)2
5th

CH(CH3)2
least stable

3. Name the following compounds using IUPAC nomenclature.

a)

b)

c)

OH

d)

e)

CH3

Cl

4. Draw all constitutional isomers with the formula C4H10O.

5. Consider the molecule drawn below.

H2N
CO2H

N
HO

Draw the form of this compound that would be obtained if it was dissolved in a non-aqueous
solvent and treated with:
a) one equivalent of the very strong base CH3- Li+

b) two equivalents of the very strong base CH3- Li+

6. The alcohol shown below has a much lower pKa than a normal alcohol.
HO

NO2

a) Draw the anion formed upon deprotonation of this alcohol showing all lone pairs and formal
charges.

b) Draw all relevant resonance structures of the anion that help explain why the pKa of the
alcohol is low.

7. a) Give a line drawing for the molecule ozone (O3) showing all lone pairs and formal charges.

b) Is ozone a linear or bent molecule? Explain.

c) Draw two resonance structures that contribute most to the overall picture of ozone.