1.
Draw the structure of the following compounds. Include all hydrogens in the structure
(i.e. CH3CH3 rather than C-C for ethane).
a) 2,2-dimethylbutane
b) 1-ethyl-4-isopropylcyclohexane
c) cis-2-hexene
d) ethylene
e) (Z)-2-bromo-2-pentene
2.
3.
Hydrocarbon X has 50 carbons, 2 π bonds, and one ring.
How many hytdrogens are present in a molecule of X ?
Complete the following Newman projection for the most stable conformation
of octane viewed down the C3-C4 bond.
Answer
Complete the wedge-dotted line structure for the following Newman projection:
4.
CH3
H
Br
H
H
CH3
H
Br
How many of the four methyl groups in the following structure will be equatorial
in the more stable chair conformation?
5.
CH3
CH3
CH3
CH3
Indicate (in the boxes) the isomer relationship between the following pairs.
Your only choices are constitutional, configurational, or conformational:
6.
H
a)
and
CH3
CH3
H
H
H
H
b)
CH3
CH3
CH3
and
H
CH3
CH3
H
H
CH3
7.
Indicate (in the boxes) the acids and the bases in the following acid-base reaction:
O
O
F
S
OH
+
O
HO
S
O
OH
FS
(-)
O
+
H
O
O
H +
O
Br
8.
CHCH2CH3
Br
X
For the above structure X:
9.
a)
How many chirality centers are present
in the structure of X?
b)
How many configurations are possible for
molecules with the constitution of X?
Give the formal charge on the indicated atom in the following structures:
CH3
CH3
a)
CH3
b) CH3
C
CH3
C
CH3
O
S
O
OH
energy
A
B
C
progress of reaction
9.
For the above energy diagram:
a)
Which product (A, B or C) is formed at
the slowest rate?
Answer
b)
Which product (A, B or C) is most stable?
Answer
10.
H
CH3
OH
H
CH3
H
CH3
H
OH
HO
HO
HO
CH3
H
A
a)
OH
CH3
CH3
H
C
B
Which one of the above structures (A, B or C)
would have (2R, 3R) as its configuration prefix?
Answer
b)
Which two of the above structures are
related as enantiomers?
+
Answer
c)
Which one is properly termed a ‘meso compound’?
Answer
d)
Which one is an achiral molecule?
Answer
Answer
Br
Br
Br
CH3
A
11.
Br
CH3
CH3
B
CH3
D
C
For the above four structures (A, B, C & D):
a)
Which one is (1R, 2S)-1-bromo-2-methylcyclohexane?
Answer
b)
Which one is identical to X (below)?
CH3
Answer
H
H
X
c)
Br
Which one is the enantiomer of A?
Answer
d)
Which two are diastereomers of B?
and
Answer
Answer
e)
If C has a specific rotation of (+)20o, which one
must have a specific rotation of (-)20o?
Answer
f)
Which one would be mixed with D to form
a racemic mixture?
Answer
12.
(+)
H
(+)
CH2
CH3
A
CH3
(+)
C
B
Which of the above three carbocations (A, B or C) is the most stable?
Answer
13.
CH3
CH2
CH3
A
C
B
Which of the above three olefins (A, B or C) releases the least
heat upon catalytic hydrogenation to form methylcyclohexane?
Answer
14.
Draw the structure of Compound X (C10H16) in the box,
based on the following ozonolysis result:
1) O3
2) Zn,
H3O+
Compound X
(C10H16)
CH3
O
O
C
C
CH2
O
+
CH3
O
C
H
C
H
C
CH3
CH3
15. Draw the structure of the major organic product of the following reactions.
a)
1) BH3
CH3
2) H2O2, NaOH
show stereochemistry
b)
CH3
C
H2O,
CHCH2CH3
H2SO4
CH3
c)
CH3
C
CHCH2CH3
CH3
d)
1) Hg(OAc)2, H2O
2) NaBH4
H
H
C
CH3
OsO4
C
show stereochemistry
O
C
e)
O
O
H
CH3
H
C
CH3
NMO
CH3
CO2H
Cl
C
+
H
Cl
show stereochemistry
16. Draw the structure of the olefin monomer (in the box) used to make the following polymer:
ROOR
CH2
CH
CH2
CH
polymer
olefin monomer
CH2
CH
17. Draw appropriate structures in the boxes:
a)
CH3
C
CH3
CHCH2CH3
+
HBr
more stable carbocation intermediate
major organic product
b)
CH3
+
Br2/H2O
bromonium ion intermediate,
show stereochemistry with
wedge/dotted lines
c)
major organic product,
show stereochemistry
CH2
CH
HCl
initial carbocation
1,2 hydride shift
Cl(-)
organic product
rearranged carbocation