Chemistry 201-101
Test # 1
Dr. Richard Rogers
September 10, 2009
Name: _____________________________________________
1. What is the relationship between the following atom(s) X? Include the identity of X in
your answer. (1 point each).
a) 13X and 11X
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b) 14X and 14X
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2. Draw a Lewis structure for each species. (2 points each)
a) CH3C(NH)NH2
b) CH3CH2CH(OH)CN
c) CH3CH2CHO
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3. Show the electronic configuration for phosphorous (P). (2 points)
4p
3d
4s
3p
3s
2p
2s
E
n
e
rg
y
1s
4. Show the dipole moment (
or zero, label it N. (1 point each).
a) H 3 C CH 3
b)
Cl3 C Cl
e)
H3C Mg
) for the indicated bonds. If the dipole moment is low
c)
H
d) H3C O
2
H 2C O
5. Draw the resonance structure(s) for the following ion. (5 points).
CH2
6. Label the following as either resonance forms (RF) or different compounds (DC). (2
points each).
OH
O
a)
b)
N
H
CH3
H
H
N
H
H3C
H
H
H
H
H
c)
H
O
OH
H 3C C
d)
H
H
H
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7. In the following reaction, label each reactant/product as an acid (A), base (B),
conjugate acid (CA) or conjugate base (CB). (4 points).
H
H 3C O
H
+
H 3C
O
+
CH3OH
CH3
H3 C
H
O
CH3
8. Label each reactant in the following reactions as either an electrophile (E) or
nucleophile (N) and use curved arrows to show the movement of electron pairs in each
reaction. (4 points each).
H 3C
a) (CH3)3P
H
b)
CH3CH2
H3C P CH2CH3
H3C
Br
H
+
C C
H
+
H2C CH2Br
Br Br
H
HO
c)
B(OH)3
+
H2O
D
B
O
HO
H
HO
4
+
Br
+
Br
9. What is a bond? Use 10 words or less. (3 points).
10. In each case given below, what kind of molecular orbital (σ, σ*, π, π*) would result
when the two indicated atomic orbitals interact in the manner indicated? Note: lighter
shade indicates a positive phase, while the darker shade indicates a negative phase. (1
point each).
a)
b)
c)
d)
11. Give the hybridization of each indicated atom. (1 point each)
N
O
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12. Acetaldehyde is shown below. Answer the following questions about this molecule.
(1 point each).
O
H3C
H
a) What is the shape of the methyl carbon?
b) What is the shape of the carbonyl carbon?
c) What is the CCO bond angle?
d) In the methyl group, what is the HCH bond angle?
13. For the indicated molecule, answer the following questions. The numbers-1,2,3,4,5serve only to identify each carbon. (1 point each).
O
H H
5 H
C
1
3 C O
H
C C C4
H 2
H
a) How many pi bonds are present?
b) How many p orbitals are present?
c) How sigma bonds are present?
d) What is the angle formed by C2C3C4?
e) Is there free rotation around the C4C5 bond?
f) Is there free rotation around the C2C3 bond?
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14. For each pair of compounds shown below, tell whether they are constitutional
isomers (CI), stereoisomers (SI) or non-isomeric (NI). (1 point each).
a)
b)
c)
CH3
Br
H3C
H3C
Br
Br
Br
Br
Br
CH3
Br
d)
H3C
CH3
H3C
CH2Br
H
15. Label each molecule below as a hydrogen bond donor (D), hydrogen bond acceptor
(A) or both (B). (1 point each).
O
a)
O
b)
NH
OH
c)
O
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16. Classify each of the following molecules as to what functional group each contains,
i.e. ketone , cycloalkene , etc. (1 point each).
a)
OH
b)
O
N
c)
O
d)
O
e)
f)
N
H
g)
O
17. Using the line-angle method, draw the structure of 4-t-butyl-2-cyano-6-fluoro-5hydroxy-2-methyloctane. (3 points).
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18. Using the Newman projection and looking along the C1C2 axis, draw and label the
totally eclipsed, gauche (staggered) and anti (most stable) forms of 1-fluoropropane. (2
points each).
19. Using a perspective drawing (wedges and dashed lines), draw the anti conformer of 1fluoropropane and the cis isomer of 1,2-dimethylcyclopropane. (2 points each).
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20. Using the line-angle method, draw the boat and chair conformers of cyclohexane.
Clearly show the axial and equatorial bonds on each structure. For clarity, do not add
“H” or any other substitute to these bonds. (2 points each).
21. Using the line angle method, draw the conformations of the following compounds. In
each case circle the more stable conformation. Only show the exocyclic bonds bonded to
the named substitutes, i.e. do not show any “H”s or their bonds. (3 points each).
a) cis-1-iodo-2-methylcyclohexane
b) trans-1,3-dimethylcyclohexane
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