Name: ANSWER KEY 1

Chemistry 110B -- Exam #2 Answer Key -- October 20, 2006

To receive full credit you must show your work. Show nonzero formal charges on all Lewis
structures. Circle final answers. There are 4 pages of exam.

1. (6 points) Give formulas (not Lewis structures) for the following:

a) Sulfuric Acid b) Lithium carbonate c) Calcium chloride

H2SO4 Li2CO3 CaCl2

2. (6 points) Name the following compounds:

a) K3PO4 b) V2O3 c) HNO3

Potassium phosphate Vanadium(III) oxide Nitric acid

3. (18 pts) a) Draw the Lewis structure for N2F2. (Hint: There is one fluorine atom on each
nitrogen.)
•• •• •• ••
•• F N N F ••
•• ••
b) What is the name of N2F2? Dinitrogen Difluoride

c) Estimate the FNN bond angle in N2F2? Slightly less than 120°

d) What is the hybridization on the nitrogen atoms? sp2

e) Show (and clearly label) the valence orbitals involved in the bonding of N2F2. Draw two
sketches, one showing the sigma bonds and one showing the pi bonds. Be sure to clearly show the
orientation of the orbitals relative to the atoms in the molecule.

F N N F
F F

"sideways" overlap N N p-orbital on F

of p-orbitals leads sp2 hybrid orbital on N
to a pi bond
overlap of two
sp2 orbitals (one from
each N)
The other sp2 orbital on each
N is not shown, but contains the
lone pair electrons.
f) There are actually two different isomers (cis and trans) of N2F2, one has a dipole moment and the
other does not. Draw structures for the two isomers and circle the one that has a dipole moment and
show the direction of the dipole.

F F F
N N N N
F
trans cis
Name: ANSWER KEY 2
4. (12 pts) Draw Lewis structures of the following compounds. Show all non-zero formal charges.

a) Methanol (CH3OH)
H
••
H
C O H
••
H
b) Formate ion (HCO2-, all atoms are connected to the carbon; show all important resonance
forms)
•• O •• •• ••
O ••
C •• C ••
H O •• H O
•• ••
c) What is the bond order for the CO bonds in formate (circle best answer)?

1) 1 (i.e., both are single bonds)

2) 1.5
3) 2 (i.e., both are double bonds)
4) one of the CO bonds is a single bond, the other is a double bond
5) the CO bonds are single half of the time and double half of the time

5. (12 pts) Write balanced equations to describe the following processes. Be sure to indicate the
physical states of the products and reactants (g,l,s,aq).

a) One of the components of gasoline is toluene (C7H8). Write a balanced reaction for the
combustion of toluene in a car.

C7H8(g or l) + 9 O2 (g) 7 CO2 (g) + 4 H2O(g or l)

b) An aqueous solution of barium nitrate added to an aqueous solution of sodium sulfate forming a
white precipitate. (Write the balanced, overall "molecular equation". See useful information page.)

Ba(NO3 )2 (aq) + Na2 SO4 (aq) BaSO4 (s) + 2 NaNO3 (aq)

c) Write the net ionic equation for the reaction in part c.

Ba2 +(aq) + SO4 2-(aq) BaSO4 (s)

Name: ANSWER KEY 3
6. (6 pts) Describe how to prepare 500 mL of a 0.30 M aqueous solution of KOH from solid KOH.
(Show your calculations.)

(0.500 L)(0.30 mol/L) = 0.15 moles of KOH needed

Formula Weight for KOH = 39.10 + 16.00 + 1.008 = 56.108 g/mol
(0.15 moles KOH)(56.108 g/mol) = 8.42 g KOH

To prepare the solution place 8.42 g of the KOH in a 500 mL volumetric

flask. Then fill it about half full with water and stir until the KOH dissolves.
Make up to the mark with water and mix thoroughly.

7. (18 pts) There are two stable compounds that contain a central phosphorus atom attached to
chlorine atoms (PCln, where n is an integer).

a) Based on your knowledge of what types of compounds are stable draw Lewis structures for these
two compounds.
sp3
Cl
Cl P Cl Cl Cl
P
Cl sp3d
Cl Cl
Phosphorus Phosphorus
trichloride pentachloride
b) Name these two compounds

c) Indicate the hybridization on the phosphorus for each of these compounds.

d) Draw accurate 3-dimensional sketches of these compounds.

Cl
P
120° between Cl P Cl Cl Cl
groups in the Cl Cl
equatorial positions Cl 90° between axial slightly less
and equatorial positions than 109.5°
trigonal bipyramidal trigonal pyramidal
nonpolar polar
e) Indicate the Cl-P-Cl bond angles in these compounds.

f) Name the molecular geometry of these compounds.

g) For each molecule label it as polar or nonpolar. If it is polar show the direction of the overall
dipole.

h) There is only one stable compound that contains a central nitrogen atom attached to chlorine
atoms (NCln, where n is an integer). What is the value of n for this compound, and why is there
only one compound, not two like in the phosphorus case?

N = 3, i.e., NCl3. Nitrogen does not have low lying d-orbitals that can be used to form bonds.
Thus, it cannot "expand its octet" and form 5 bonds like phosphorus can.
Name: ANSWER KEY 4
8. (8 pts) An organic chemist reacted 9.5 g of dibromopropane (C3H6Br2) with an excess of sodium
cyanide (NaCN) and isolated 2.8 g of dicyanopropane (C5H6N2) as shown in the reaction below:

C3H6Br2 + 2 NaCN C5H6N2 + 2 NaBr

9.5 g excess 2.8 g

Calculate the percent yield for this reaction. (Show your work.)

MW of C3 H6 Br2 = 3(12.01) + 6(1.008) + 2(79.90) = 201.88 g/mol

MW of C5 H6 N2 = 5(12.01) + 6(1.008) + 2(14.01) = 94.12 g/mol

(9.5 g C3 H6 Br2 )/(201.88 g/mol) = 0.047 moles C3 H6 Br2

Since each mole of C3 H6 Br2 produces one mole of C5 H6 N2 ,

the theoretical yield of C5 H6 N2 is 0.047 moles.

Theoretical yield: (0.047 moles C5 H6 N2 )(94.12 g/mol) = 4.43 g C5 H6 N2

Percent yield: (2.8 g actual/ 4.43 g theoretical)* 100 = 63 % yield

9. (6 pts) Complete the following Lewis structures for CH3NCO by adding lone pairs on the
appropriate atoms. Then assign formal charges and rank the resonance structures in importance,
from most to least.

H H H
•• • •• •• •• •
H C N
•• C O • H C N C O
•• H C N C O
•• •
H A H B H
C

B C A
> >
most important least important

10. (8 pts) Draw a molecular orbital diagram for the molecule NO (nitric oxide) and use it to answer
the following questions:

a) What is the bond order in NO? 2.5

_
b) Is the anion NO paramagnetic? Explain briefly.

Yes. It is isoelectronic with O2, and like O2 it would have two unpaired electrons so it would
be paramagnetic. (Recall that Hunds’ Rule states that when we have two orbitals at the same
energy level, we put one electron in each orbital before we start pairing electrons in the
orbitals.)

c) Is the bond length in the NO+ ion longer or shorter than in NO? Explain briefly.

Shorter. We are removing an electron from an antibonding orbital when we go from NO to

NO+, so the bond order gets higher (from 2.5 -> 3). This results in a stronger bond leading to
a shorter bond length.
Name: ANSWER KEY 5

*
!2p

"*
2p 2p
2p
!2p
" 2p

!*
2s 2s
2s
!
2s

*
!1s
1s
1s
!1s

AO's of N MO's of AO's of O

NO