CHEM 232 Discussion Section Worksheet 3

1. For sets a-c below, build 3D models of the given molecules to help you convert between
structures. Then, fill in the two empty boxes with the requested name or structure.

Set Name Lewis Structure Newman Projection

a. 3-iodo-2,4-dimethyl-3-
(1-methylethyl)pentane

Along C2àC3 based on name

b.

H Cl

Along bond given by eyeball

c.

H H2 H
Br C H
H C
H H2 H F

1
2. Starting with the Newman projection you drew problem 1 part b, i) proceed to generate five
more conformations by rotating around the bond in 60 degree increments, ii) label the
conformations as staggered or eclipsed, and iii) identify gauche interactions with the “)(“
symbol.

3. Now perform a conformational analysis of the Newman projections you drew in problem 2.
Provide the relative energies of the different conformations on the energy diagram shown
below.

2
4. Complete the chair structure for the ring found in problem 1 part c by adding appropriate
axial or equatorial substituents to the stencil provided. Then use the model you built to help
you draw the chair after it has been “flipped.”

flip!

5. What are the three types of ring strain? Provide an example of each type.

a.

b.

c.

6. What is the degree of unsaturation for the given molecule?

Cl

N
O
N
Formula: C17H15ClN2O