CHEM 202 Exam 2
Name ______________________________
1. (24 pts) Name the following alkanes, alkenes and alkynes using IUPAC nomenclature:
a)
b)
Br
d)
c)
2. (12 pts) Give proper line-angle structures for the following IUPAC names:
a) cis-1-iodo-3-heptene
b) trans-1,3-dimethylcyclohexane
3. (4 pts) a-Farnesene is a compound found in the waxy coating of apple skins. Complete the systematic name by
indicating the proper E or Z designation in the blanks (__) provided. If an E/Z designator is not appropriate, place an
X in the blank.
3,7,11-trimethyl-(1___,3___,6___,10___)-docecatetraene
4. (4 pts) In the space provided draw the lowest energy conformer of 2-methylbutane, looking down the C2-C3 bond
using a Newmann projection:
5. (6 pts) Shown below is a chair conformer of trans-3-methylcyclohexanol. In the space to the right of the equilibrium
arrows draw the other chair conformer that comes about from the ring flip:
6. (6 pts) Label each of the six groups shown on the following isomer of menthol as axial or equatorial. Do you think this
is the lowest energy conformer? Why or why not?
H
H
H 3C
H
OH
7. (4 pts) List the strongest type of strain that exists in each structure. If no strain exists write “none”.
1
_______________________
_______________________
_______________________
o
o
o
_______________________
o
8. Classify the following functional groups by name and substitution (1 , 2 , 3 or 4 ).
9. Rank the following compounds in order of increasing boiling point (1 – lowest bp, 4 – highest bp):
10. Rank the following analgesics in order of increasing water solubility (1 – least soluble, 4 – most soluble):
Which drug do you think gets into the bloodstream the fastest? ________________________ Which drug do you
think has the longest lifetime in the tissues (think carbon chains in fatty acids)? ________________________
11. Show the mechanism for the addition of H—Cl to 1-propene below. Place arrows indicating the proper movement of
electrons and indicate any intermediates and the product(s) formed.
Reaction 1
12. Given the following diagram, label the following:
Reaction 2
d
b
g
c.
d.
e.
k.
m.
i
c
k
h
a
f
e
j
m
Which reaction is faster overall? _____ How many steps are in each reaction? _____ What step determines the
overall rate for reaction 2? ______ Which reaction is overall more exothermic? _____ The process a à c would
best be described as __________ from a thermodynamic point of view. The process h à j would best be
described as _________ from a kinetic point of view. What is the most stable species shown above? _____
What is the least stable? _______
2
CHEM 202 Exam 2
Name ________KEY_____________
13. (24 pts) Name the following alkanes, alkenes and alkynes using IUPAC nomenclature:
a)
b)
E-3,5-dimethyl-3-heptene
3-bromo-1-methylcyclohexene
d)
Br
c)
2-ethyl-1,5-dimethylcycloheptane
5-sec-butyldecane
14. (12 pts) Give proper line-angle structures for the following IUPAC names:
a) cis-1-iodo-3-heptene
b) (Z)-3-methyl-3-octene
15. (4 pts) a-Farnesene is a compound found in the waxy coating of apple skins. Complete the systematic name by
indicating the proper E or Z designation in the blanks (__) provided. If an E/Z designator is not appropriate, place an
X in the blank.
3,7,11-trimethyl-(1_X_,3_E_,6_E_,10_X_)-docecatetraene
16. (4 pts) In the space provided draw the lowest energy conformer of 2-methylbutane, looking down the C2-C3 bond
using a Newmann projection:
17. (6 pts) Shown below is a chair conformer of trans-3-methylcyclohexanol. In the space to the right of the equilibrium
arrows draw the other chair conformer that comes about from the ring flip:
18. (6 pts) Label each of the six groups on the following isomer of menthol as axial or equatorial. Do you think this is the
lowest energy conformer? Why or why not?
3
19. (4 pts) List the major type of strain that exists in each structure. If no strain exists write “none”.
Angle
Steric
None
o
torsional
o
o
o
20. Classify the following functional groups by name and substitution (1 , 2 , 3 or 4 ).
21. Rank the following compounds in order of increasing boiling point (1 – lowest bp, 4 – highest bp):
22. Rank the following analgesics in order of increasing water solubility (1 – least soluble, 4 – most soluble):
Which drug do you think gets into the bloodstream the fastest? Asprin (water soluble) Which drug do you think has
the longest lifetime in the tissues (think fatty acids)? Ibuprofen – soluble in non-polar
23. The addition of hydronium to an alkene follows a similar mechanism to the addition of H—X. Identify the nucleophile
and electrophile. Place an arrow indicating the proper movement of electrons and indicate the initial products formed.
Electrophile
Nucleophile
Reaction 1
24. Given the following diagram, label the following:
c.
d.
e.
k.
m.
Reaction 2
d
b
g
Intermediate
Transition state
Products
Energy
Reaction progress
i
c
k
h
a
f
e
j
m
Which reaction is faster overall? 2 How many steps are in each reaction?
2 What step determines the
overall rate for reaction 2? 1 or g Which reaction is overall more exothermic? 1 The process a à c would best
be described as endothermic from a thermodynamic point of view. The process h à j would best be described
as fast from a kinetic point of view. What is the most stable species shown above? e What is the least stable?
d.
4