Chapter 1 – Structure and Bonding

1. How many total valence electrons are represented in the following electron configuration?

1s22s22px2 2py2 2pz1 or 1s22s22p5

a. 1
b. 3
c. 5
d. 7
e. 9

ANS: d

Write valid Lewis (electron-dot) structures for each formula below. Show all electrons as dots and
show all nonbonding electrons.

2. CH3CH2OH ethanol

ANS:
H H

H C C O H

H H

3. The structure of urea is shown below. Fill in any nonbonding valence electrons that are missing from
the line-bond structure.
O

H2N C NH2
ANS: :O :
.. ..
H2N C NH2

Determine the hybridization for the indicated atoms in each structure below.

A B
O

CH3 CH2 C O H CH3 C N

4. The hybridization of carbon atom A is .

ANS: sp2

5. The hybridization of carbon atom B is .

ANS: sp

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6. How many nonbonding electron pairs are in the structure shown below?
H O

H C C OH

H
a. 2
b. 4
c. 6
d. 8
e. none of the above

ANS: b

7. The molecular formula C2H4O can be converted into three-line bond (Kekulé) structures that are
consistent with valence rules. Which one of the following Kekulé structures is not consistent with
valence rules?
H O H H O H H
a. H C C H b. C C c. H C C H d. C C O

H H O H H H H H

ANS: d

Propose a structure for a molecule that meets the following description.

8. Contains only two sp3 hybridized carbons and two sp hybridized carbons.

ANS:
CH3 C C CH3 or CH3 CH2 C CH

9. Contains only one sp3 hybridized carbon and two sp2 hybridized carbons.

ANS: H3C C CH2

10. Consider the formation of an sp2 hybrid orbital. Which of the following is true?
a. Four equivalent hybrid orbitals are produced.
b. One s and one p atomic orbital are involved.
c. One p atomic orbital remains unhybridized.
d. The hybrid orbitals produced can form π bonds.
e. none of the above

ANS: c

11. According to atomic theory:

a. the nucleus is positively charged.
b. the nucleus contains both charged and uncharged particles.
c. the electrons contribute very little to the total mass of the atom.
d. the electrons are located in the atomic space outside the nucleus..
e. all of the above

ANS: e

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12. In drawing the Lewis structure for an organic compound, the carbon atoms should always be shown
with
a. lone pairs of electrons.
b. four single bonds.
c. eight total electrons.
d. a positive charge.
e. none of the above

ANS: c

13. Covalent bonding

a. involves a transfer of electrons from one atom to another.
b. occurs when atoms share all their valence electrons.
c. occurs when unpaired valence electrons are shared between atoms.
d. occurs when nonvalence electrons are shared between atoms.
e. none of the above

ANS: c

14. Which of the following best represents the shape of a 2p atomic orbital of carbon?

1 2 3 4
a. 1
b. 2
c. 3
d. 4

ANS: b

15. Which of the following best represents the shape of a sp3 hybrid orbital of carbon?

1 2 3 4

a. 1
b. 2
c. 3
d. 4

ANS: c

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16. How many electrons are there in the valence shell of the carbon atom of a methyl anion, CH3-?
a. 5
b. 6
c. 7
d. 8

ANS: d

17. Which of the following statements is not true?

a. The carbon-carbon single bond of an alkane is weaker than the carbon-carbon triple bond of an
alkyne.
b. The carbon-carbon triple bond of an alkyne is shorter than the carbon-carbon double bond of an
alkene.
c. The carbon-carbon triple bond of an alkyne is exactly three times as strong as a carbon-carbon
single bond of an alkane.
d. The carbon-carbon single bond of an alkane is longer than the carbon-carbon triple bond of an
alkyne.

ANS: c

18. Draw all the lone pairs (nonbonding valence electrons) on the structure of phosgene, a poisonous gas
once used as a chemical warfare agent.

C
Cl Cl

ANS:
O

C
Cl Cl

19. Specify the hybridization of each carbon atom of limonene, a natural product present in citrus fruits,
and thujone, which is derived from wormwood, a traditional component of the notorious liquor,
Absinthe.

CH3 CH3

H3C CH2 H3C CH3

limonene thujone

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 ANS:
sp3 sp3
CH3 CH3
sp2 sp3
O
sp3 sp2 sp3
sp2
sp3 sp3 sp3 sp3
sp3

sp2 sp3
sp3 sp2 sp3 sp3
H3C CH2 H3C CH3
limonene thujone

20. Convert the skeletal drawing of the pharmaceutical Vioxx into a molecular formula.

CH3SO2

ANS: C17H14O4S

21. Draw a picture showing the orbitals involved in the π-bonds of cyclopenta-1,3-diene, a commonly
encountered reagent in organic synthesis.

ANS:

5
22. Draw all possible structures of CFnClm where n and m vary from 0 to 4.

ANS:

F F F F Cl

C C C C C
F F F Cl Cl
F Cl Cl Cl Cl
F F Cl Cl Cl

23. Draw two possible isomers of C6H6 in which all the carbon atoms are sp2 hybridized.

ANS:

and or: or:

24. Draw the structure for CCl2F2 using solid, wedged, and dashed lines to show the tetrahedral geometry.

ANS:
F

C
F
Cl
Cl

Consider the following two structures.

CH3CH2OH CH3OCH3

25. Which of the following correctly describes the structure of these compounds?

a. All carbon atoms are sp3 hybridized.

b. All of the bonds are sigma bonds.
c. Each oxygen atom has two nonbonding pairs of electrons.
d. The bond angle around each oxygen atom is ideally about 109.5o.
e. All of the above

ANS: e

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26. What is the expected hybridization around the sulfur atom in diethyl sulfide?

CH3CH2 S CH2CH3
a. sp
b. sp2
c. sp3
d. The sulfur atom is not hybridized.

ANS: c

27. Which of the following statements is not true according to molecular orbital (MO) theory?
a. Antibonding orbitals are higher in energy than the corresponding bonding orbital.
b. The head-on overlap of an s and a p atomic orbital can produce a σ molecular orbital.
c. A π molecular orbital forms only from the combination of p atomic orbital wave functions.
d. The subtractive combination of atomic orbital wave functions produces a bonding molecular
orbital.

ANS: d

28. The molecular orbital shown below is most likely of what type?

a. σ bonding
b. σ antibonding
c. π bonding
d. π antibonding

ANS: c

29. In the two structures shown below, what do the positions labeled with the arrow have in common?

OH OH

a. the same type of hybridization on the carbon atom

b. the same geometry around the carbon atom
c. the same number of hydrogen atoms bonded to the carbon atom
d. both carbon atoms are involved in a π bond

ANS: c

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30. The following species forms during an organic reaction.

H H

H C C

H H

What is the formal charge on the carbon atom indicated by the arrow?
a. 0
b. +1
c. −1
d. +2
e. −2

ANS: b