Study guide for Chapter 1

You should be able to perform the following tasks from Chapter 1:

1) Atoms and Molecules
a. Determine the number of valence electrons for all atoms
b. Draw a reasonable Lewis structure or Kekule structure for a given molecular formula
c. Calculate formal charge
d. Be able to draw the condensed formula, Lewis structure, Kekule structure, and line drawing
(or skeleton structure) of all molecules.
2) Resonance
a. Be able to draw all resonance contributors of a molecule
b. Be able to identify the major resonance contributor of a molecule
3) Electronegativity and Polarity
a. Know the electronegativity trend of atoms using the periodic table (you do not need to
memorize any values)
b. Identify an ionic, polar covalent, and nonpolar covalent bond
c. Indicate the direction of polarity of a polar molecule (you do not need to memorize any
values)
4) Molecular Orbitals and Bond Strength
a. Be able to draw an orbital interaction diagrams for s + s, s + p, and p + p
b. Identify a sigma () or pi () bonds in a molecule
c. Be able to draw an energy diagram for an exothermic or endothermic reaction (you do not
need to memorize any values)
d. Identify a Lewis acid and a Lewis base.

Practice Problems for Chapter 1

1) For the following molecular formulas, draw a reasonable Lewis structure.
a) C2H2
b) PBr3
2) For the following compounds, draw the Lewis or Kekule structure of the following condensed
structures. Indicate the formal charge of each atom. Also, draw the line drawing for part b.
a) CH2N2
b) (CH3)2CHBr
3) Draw the Kekule structure and condensed structure for the following line drawings.
a)
b)
c)
4) Draw the condensed structure and the line drawings for the following Kekule structures.
H H O
a)
b)
H H H H
H C C C O H

H C C C C H

H H

H H H H

5) Indicate if the following compounds are polar or nonpolar. If polar, indicate the direction of the
dipole.
a) CH3CH3
b) CH3OCH3
c) CH3COCH3
6) Are the following pairs resonance structures?
a)
O

H3 C

b)

C
H

O
H3 C

CH2

and

H3 C

OH
C
H2

CH

CH3

and

H3 C

C
H

CH2

OH

CH

C
H2

CH3

7) Draw the resonance contributors for the following condensed structures. Indicate which resonance
contributor is the most stable.
a) HCO3b) CH3CH2COCH3
8) Designate the Lewis acid and Lewis base in the following reactions.
a) NH3 + H2O -- NH2- + H3O+
b) NH3 + H2O -- NH4+ + HOc) Br3B + NH3 - Br3B-NH3+
9) Draw a reaction progress (or reaction coordinate) diagram for a theoretical reaction that is has a
H of -40 kcal/mole.
10) Draw a full molecular orbital diagram for s + p, where each atomic orbital contributes one electron
to the bond.