Chapter 1 – Structure and Bonding
1. Give the ground-state electron configuration for carbon (atomic number 6).
Answer: 1s22s22px12py1 or 1s22s22p2
2. Give the ground-state electron configuration for fluorine (atomic number 9).
Answer: 1s22s22px2 2py2 2pz1 or 1s22s22p5
3. Give the ground-state electron configuration for magnesium (atomic number 12).
Answer: 1s22s22p63s2
4. How many electrons does silicon have in its valence shell?
Answer: four
Write valid Lewis (electron-dot) structures for each formula below. Show all electrons as dots and show all
non-bonding electrons.
Cl
5. C2Cl4 tetrachloroethylene Answer: Cl C C Cl
Cl
6. CO2 carbon dioxide Answer: O C O
7. CH4O methanol
H
Answer: H CO H
H
8. The structure of urea is shown below. Fill in any non-bonding valence electrons that are missing from the
line-bond structure.
O
H2N C NH2
:O :
Answer: .. ..
H2N C NH2
9. The structure of urea is shown below. The carbon atom in urea is:
O
H2N C NH2
3
a. sp hybridized
b. sp2 hybridized
c. sp hybridized
d. not hybridized
Answer: b. sp2 hybridized
Test Items for McMurry’s Organic Chemistry, Seventh Edition 1
10. The structure of urea is shown below. The predicted NH2-C=O bond angle in urea is:
O
H2N C NH2
a. 109.5
b. 120
c. 180
d. not predictable
Answer: b. 120
Determine the hybridization for the indicated atoms in each structure below.
11.
13. 14.
O 12.
CH3 CH2 C O H CH3 C N:
11. The hybridization of this oxygen atom is .
Answer: sp2
12. The hybridization of this oxygen atom is .
Answer: sp3
13. The hybridization of this carbon atom is .
Answer: sp3
14. The hybridization of this carbon atom is .
Answer: sp
15. The molecular formula C2 H 4O 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
Answer: d
16. Explain why the structure you chose in question 15 is not consistent with valence rules.
Answer: The carbon bonded to the oxygen atom in structure d is pentavalent; it has 10 valence electrons.
Carbon can only have eight valence electrons. In addition, the other carbon has only six valence
electrons when it would prefer to have eight.
2 Chapter 1: Structure and Bonding
17. Convert the following structure to a skeletal drawing and give its molecular formula
H Br
H C
H
C C
H C C
H H
H
3-bromo-1-cyclopentene
Answer:
Br
Molecular formula: C5H7Br
18. Draw an orbital picture for acetylene, C2H2. Clearly label each bond type and indicate the type of orbitals
involved in each bond.
Answer:
pi bonds
sp-s sp-s
sigma bond sigma bond
H C C H
sp-sp
sigma bond
pi bonds
Propose possible structures for a molecule that meets each of the following descriptions:
19. Contains two sp3 hybridized carbons and two sp hybridized carbons.
Answer:
H C C CH2CH3
H3C C C CH3
20. Contains one sp3 hybridized carbon and two sp2 hybridized carbons.
Answer:
H3C C CH2
Test Items for McMurry’s Organic Chemistry, Seventh Edition 3
