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Organic Chemistry Chapter 1 HW Key

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SoLVE Chemistry 210
Chapter 1
Review of General Chemistry
1) Draw Lewis structures for each of the following compounds. Predict the molecular geometry,
approximate bond angle and hybridization of the atoms in red. (Old SoLVE Activity and 1.53 from
book)
a. H2O
b. BF4c. CH3CH2OH
d. CH2O
e. C2H4
f.
C2H2
g. CH3OCH3
h. CH3NH2
i.
C3H8
j.
NH3
k. CH4O
l.
C2H3N
m. CH3CN
Note to Facilitators:
Show students page 28
Show students the
hybridization trick with
your fingers.
2) Indicate the hybridization of the orbitals on each carbon, and predict an approximate value for each
bond angle. How many bonds and  bonds are present in the following compounds? (testbank q.
112 and 113 and Old SoLVE Activity)
bonds and 8  bonds
bonds and 2  bonds
bonds and 1  bonds
bonds and 2  bonds
bonds and 6  bonds
3) Determine the formal charge of the atom highlighted in red. Determine the formal charge of the
atom highlighted in red. (Old SoLVE Activity)
4) Draw ONE Lewis structure for a molecule that satisfies the following requirements. (Old SoLVE
Activity)
a. The molecule has 2 carbon atoms, 2 oxygen atoms and 4 hydrogen atoms.
b. The molecule has 7 sigma bonds
c. The molecule has 1 pi bond
d. The molecule has 4 lone pairs
5) Identify the most electronegative element in each of the following compounds:
a.
oxygen
b.
fluorine
c. CH3Li carbon
6) For each type of bond below, determine the direction of the expected dipole moment.
7) For the following compound identify the polar covalent bonds and indicate the direction of dipole
moment using + and - (testbank q. 59, 60)
O
O
Cl
C
H
C
H
Cl
C
C
C
H
H
H
H
H
N
H
H
8) Analyze the polarity of each bond in the following organic compound. Which bond, other than the
C-C bond, is the least polar one in the molecule? Which carbon has the most partial positive
character? Explain. (Old SoLVE Activity)
9) Which of the following compounds have a molecular dipole moment? Indicate the direction
of dipole moment. (testbank q. 164, 165, 167, 168, )
10) What are the likely formulas for the following substances? (Old SoLVE Activity)
GeHx
CXH6
(more than one possibility)
NFx
C2HxO
(more than one possibility)
11) Draw two constitutional isomers for each of the following compounds. (testbank q. 5, 6 and 8)
See page 3 for definition of
constitutional isomer: same
molecular formula but
different connectivity of
atoms.
12) What is the strongest intermolecular force present in the following compound? (testbank q. 173 and
174)
H
H
H
H
H
C
C
C
C
H
H
H
H
O
H
H
H
H
H
H
C
C
C
C
H
H
H
H
Hydrogen bonding
S
H
Dipole-dipole
13) Which of the following compounds have a higher boiling point? Explain why. (testbank q. 184 and
185)
a.
Compound II has a higher boiling point than compound I. Compound II has larger surface area that
allows for stronger fleeting dipole-dipole interactions between molecules.
b.
Compound I has a higher boiling point than compound II. Compound I has hydrogen bonding
interactions between molecules. Compound II has dipole-dipole interactions that are weaker than
hydrogen bonding interactions.
Lewis, Condensed and Bond Line Structures:
1. Identify the number of carbon atoms and hydrogen atoms in the compound below:
From previous SoLVE activity
C5H12
C6H14
C8H18
C12H18
2. Draw a Lewis structure for each of the following condensed structures:
Test bank q. 3, 4, 5 and 9
(CH3)2CHCH2OH
CH3CHOH(CH2)2CHClCH3
CH2=CH(CH2)3C(CH3)3
(CH3)2N(CH2)3CH(CH3)2
3. Draw a bond-line structure for each of the following Lewis structures:
(From previous SoLVE activity)
4. Write a condensed structural formula for each of the following compounds. What is the molecular
formula for each compound? Test bank q. 15, 16, 33, 34, and 35
5. For the following transformation how many H atoms are added, lost or remained the same? Test bank
q. 25, 26 and 28
OH
O
a.
Added two
b.
c.
No change
OH
Lost two
Functional Groups:
6. Identify and name the functional groups present in each of the following molecules. (Note: there may
be more than one functional group in each molecule.)
Some questions are from old SoLVE activity and some are from test bank (50, 54, 55, 56, 58, & 59)