Midterm 2.

1 Textbook Practice Problems (Chapter 14)

9. Why do we hybridize atomic orbitals to explain the bonding in covalent compounds? What
type of bonds form from hybrid orbitals, s or p? Explain.

13. Give the expected hybridization for the molecular structures illustrated below.

16. Use the LE model to describe the bonding in H2CO and C2H2. Carbon is the central atom in
H2CO, and C2H2 exists as HCCH.

22. Indigo is the dye used in coloring blue jeans. The term navy blue is derived from the use of
indigo to dye British naval uniforms in the eighteenth century. The structure of the indigo
molecule is

a. How many s bonds and p bonds exist in the molecule?

b. What hybrid orbitals are used by the carbon atoms in the indigo molecule?
23. For each of the following molecules, write a Lewis structure, predict the molecular structure
(including bond angles), give the expected hybrid orbitals on the central atom, and predict the
overall polarity.
a. CF4 b. NF3 c. OF2 d. BF3 e. BeH2

f. TeF4 g. AsF 5 h. KrF2 i. KrF4 j. SeF6

k. IF5 l. IF3

25. Why must all six atoms in C2H4 be in the same plane?

29. Complete the Lewis structure of AZT

a. How many carbon atoms use sp3 hybridization?

b. How many carbon atoms use sp2 hybridization?

c. Which atom is sp hybridized?

d. How many σ bonds are in the molecule?

e. How many π bonds are in the molecule?

f. What is the N﹣N﹣N bond angle in the azide (ON3) group?

g. What is the H﹣O﹣C bond angle in the side group attached

to the five-membered ring?

h. What is the hybridization of the oxygen atom in the ﹣CH2OH group?

33. The three most stable oxides of carbon are carbon monoxide (CO), carbon dioxide (CO2),
and carbon suboxide (C3O2). For each oxide, draw the Lewis structure, predict the molecular
structure, and describe the bonding (in terms of the hybrid orbitals for the carbon atoms).

34. Consider the molecular orbitals formed from the combination of 2 hydrogen 1s orbitals:
a. Which is the bonding molecular orbital, and which is the antibonding molecular orbital?
Explain how you can tell by looking at their shapes.

b. Which of the two molecular orbitals is lower in energy? Why is this true.

36. What are the relationships among bond order, bond energy, and bond length? Which of
these can be measured? Distinguish between the terms paramagnetic and diamagnetic. What
type of experiment can be done to determine if a material is paramagnetic?
39. How does molecular orbital theory explain the following observations?
a. H2 is stable, whereas He2 is unstable.

b. B2 and O2 are paramagnetic, whereas C2, N2, and F2 are diamagnetic.

c. N2 has a very large bond energy associated with it.

d. NO+ is more stable than NO-.

41. Show how a hydrogen 1s atomic orbital and a fluorine 2p atomic orbital overlap to form
bonding and antibonding MOs in the hydrogen fluoride molecule. Are they s or p MOs?

42. Which of the following are predicted by the molecular orbital model to be stable diatomic
species?

44. In which of the following diatomic molecules would the bond strength be expected to
weaken as an electron is removed? a. H2 b. B2 c. C2-2 d. OF
48. Using the molecular orbital model, write electron configurations for the following diatomic
species and calculate the bond orders. Which ones are paramagnetic? Place the species in
order of increasing bond length and bond energy. a. CN+ b. CN c. CN-

49. As compared with CO and O 2, CS and S2 are very unstable molecules. Give an explanation
based on the relative abilities of the sulfur and oxygen atoms to form π bonds.

53. a. Would the bonding MO in HF place greater electron

density near the H or the F atom? Why?

b. Would the bonding MO have greater fluorine 2p

character, greater hydrogen 1s character, or an equal
contribution from both? Why? \

c. Answer parts a and b for the antibonding MO in HF

54. The diatomic molecule OH exists in the gas phase. OH plays an important part in
combustion reactions and is a reactive oxidizing agent in polluted air. The bond length and bond
energy have been measured to be 97.06 pm and 424.7 kJ/mol, respectively. Assume that the
OH molecule is analogous to the HF molecule discussed in the chapter and that the MOs result
from the overlap of a pz orbital from oxygen and the 1s orbital of hydrogen (the OOH bond lies
along the z axis).
a. Draw pictures of the sigma bonding and antibonding molecular orbitals in OH.

b. Which of the two MOs has the greater hydrogen 1s character?

c. Can the 2px orbital of oxygen form MOs with the 1s orbital of hydrogen? Explain.

d. Knowing that only the 2p orbitals of oxygen interact significantly with the 1s orbital of
hydrogen, complete the MO energy-level diagram for OH. Place the correct number of electrons
in the energy levels.

e. Estimate the bond order for OH.

f. Is the bond order of OH+ is greater than, less than, or the same as that of OH? Explain.
55. What is delocalized π bonding, and what does it explain? Explain the delocalized π bonding
system in C6H6 (benzene) and SO2.

69. Show how a dxz atomic orbital and a pz atomic orbital combine to form a bonding molecular
orbital. Assume the x axis is the internuclear axis. Is σ or a π molecular orbital formed? Explain.

72. Complete the following resonance structures for POCl3:

a. Would you predict the same molecular structure from each resonance structure?

b. What is the hybridization of P in each structure?

c. What orbitals can the P atom use to form the π bond in structure B?

d. Which resonance structure would be favored on the basis of formal charges?

73. Using molecular orbital theory, explain why the removal of one electron in O2 strengthens
bonding, while the removal of one electron in N2 weakens bonding.

74. Vitamin B6 is an organic compound whose deficiency in the human body can cause apathy,
irritability, and an increased susceptibility to infections. Below is an incomplete Lewis structure,
for vitamin B6. Complete the Lewis structure and answer the following questions. [Hint: Vitamin
B6 can be classified as an organic compound (a compound based on carbon atoms). The
majority of Lewis structures for simple organic compounds have all atoms with a formal charge
of zero. Therefore, add lone pairs and multiple bonds to the structure below to give each atom a
formal charge of zero.]

a. How many σ and π bonds exist in vitamin B6?

b. Give approximate values for the bond angles marked a through g in the structure.

c. How many carbon atoms are sp2 hybridized?

d. How many carbon, oxygen, and nitrogen atoms are sp3 hybridized?

e. Does vitamin B6 exhibit delocalized σ bonding? Explain

78. Values of measured bond energies may vary greatly depending on the molecule studied.
Consider the following reactions:

Rationalize the difference in the values of ΔH for these reactions, even though each reaction
appears to involve the breaking of only one N-Cl bond. (Hint: Consider the bond order of the NO
bond in ONCl and in NO.)

90. Use the MO model to determine which of the following has the smallest ionization energy:
N2, O2, N2-2 , N2﹣, O2+. Explain your answer
93. Carbon monoxide (CO) forms bonds to a variety of metals and metal ions. Its ability to bond
to iron in hemoglobin is the reason that CO is so toxic. The bond carbon monoxide forms to
metals is through the carbon atom:

a. On the basis of electronegativities, would you expect the carbon atom or the oxygen atom to
form bonds to metals?

b. Assign formal charges to the atoms in CO. Which atom would you expect to bond to a metal
on this basis?

c. In the MO model, bonding MOs place more electron density near the more electronegative
atom. (See the HF molecule, Figs. 14.45 and 14.46.) Antibonding MOs place more electron
density near the less electronegative atom in the diatomic molecule. Use the MO model to
predict which atom of carbon monoxide should form bonds to metals.