Chapter 1 - Structure and Bondin1!
1.
Give the ground-state electron configuration for carbon (atomic number 6).
Answer:
2.
Give the ground-state electron configuration for fluorine (atomic number 9).
Answer:
3.
li2s22p/
2p/2p/
or Is22i2/
Give the ground-state electron configuration for magnesium (atomic number 12).
Answer:
4.
li2s22PX12p/ or li2i2p2
li2i2p63i
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.
..
5.
C2Cl4 tetrachloroethylene
Answer:
6.
CO2 carbon dioxide
Answer:
7.
C~o
Answer:
8.
:CI:
:Cl:C::C.:C.l:
~.:Ql: ..
:o::c::o:
.. ..
methanol
H
H:C:O:H
.. ..
H
The structure of urea is shown below. Fill in any non-bonding valence electrons that are missing ITom the
line-bond structure.
0
" NH2
H2N- C-
:0:
Answer:
9.
..
II
..
H2N- C- NH2
The structure of urea is shown below. The carbon atom in urea is:
0
" NH2
H2N- Ca.
sp3 hybridized
b.
c.
d.
sp2 hybridized
sp hybridized
not hybridized
Answer:
b.
Test Items for McMurry's
Sp2 hybridized
Organic Chemistry,
Seventh Edition
I
r
10. The structure of urea is shown below. The predicted NH2-C=0 bond angle in urea is:
0
II
H2N- C- NH2
a.
b.
c.
d.
109.50
1200
1800
not predictable
Answer:
b. 1200
Determine the hybridization for the indicated atoms in each structure below.
11.~
13.
:0:
II
CH3- CH2- c-
..JI.
2-
H
11. The hybridization ofthis oxygen atom is -
Answer:
14.
\CH3-\c= N:
/12.
.
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 C2H4O can be converted into three-line bond (Kekule) structures that are
consistent with valence rules. Which one of the following Kekule structures is not consistent with valence
rules?
H
H
H 0
0
H
H
\
I
/
\
\
/
I
II
d. C-C=O
c. H-C-C-H
b. C=C
a. H-C-C-H
/
/
\
I
I I
I
H
H
H
O-H
H
H
H
Answer:
d
16. Explain why the structure you chose in question 15 is not consistent with valence rules.
Answer:
2
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.
Chapter 1: Structure
and Bonding
17. Convert the following structure to a skeletal drawing and give its molecular fonnula
H
H,
,/
Br
C
'C-H
/\/
\
H C-C II
H''''''\
' H
H
3-bromo-l-cyclopentene
Answer:
Br
0
Molecular fonnula: CsH7Br
18. Draw an orbital picture for acetylene, CzHz. Clearly label each bond type and indicate the type of orbitals
involved in each bond.
Answer:
pi bonds
Propose possible structures for a molecule that meets each ofthe 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 spz hybridized carbons.
Answer:
H3C- C== CH2
I
H
Test Items for McMurry's
Organic Chemistry,
Seventh Edition
3