CHE 261
Practice Final Exam
Name _______________________
A. Please select the most appropriate answer for each of the following multiple
choice questions.
1. _______ Rank the following compounds in order of increasing boiling point
OH
1
A. 1<2<3
3
2
B. 1<3<2
C. 2<1<3
D. 3<1<2
2. _______ Which of the following is NOT a gas at room temperature?
A.
B.
C.
D.
propane
propanol
propene
all of the above are gases at room temperature
3. _______ Rank the following compounds in order of increasing acidity:
acetic acid
1
A. 1<2<3
methylamine
3
HNO3
2
B. 3<1<2
C. 3<2<1
D. 2<3<1
4. _______ Rank the following compounds in order of increasing pKb:
1-butyne
1
A. 1<2<3
butylamine
2
B. 3<1<2
C. 3<2<1
sodium ethoxide
3
D. 1<3<2
5. _______ The reduction of 3-methyl-2-butanone results in the formation of
a(n)
A.
B.
C.
D.
10 alcohol
20 alcohol
30 alcohol
none of the above
6. _______ Which of the following statements is NOT true about the following
compound:
CH3
A.
B.
C.
D.
has a geometric isomer
requires R/S nomenclature
is optically active
can undergo electrophilic addition reactions
I blew it on this one!
Addition reactions are electrophilic.
Geometric isomers = cis/trans
This molecule doesn’t exhibit
cis/trans isomerism.
7. _______ Carboxylic acids are acidic because
A.
B.
C.
D.
acidic hydrogen is attached to an electronegative element
conjugate base is resonance stabilized
carbon of the carbonyl is partially positive and has an inductive effect
all of the above
8. _______ The hybridization of the nitrogen in the following molecule is:
N
A.
B.
C.
D.
sp
sp2
s2p
sp3
9. _______ The type of bonds between the carbon and oxygen atoms in the
following molecule are:
A.
B.
C.
D.
2 sigma bonds
2 pi bonds
1 sigma + 1 pi bond
3 overlapping p orbitals
O
10. _______ The combustion of one move of cyclobutane, C4H8, produces how
many moles of water?
A.
B.
C.
D.
two
three
four
five
11. _______ The most stable product of the dehydration of 2-methyl-2pentanol is:
A.
B.
C.
D.
2-methyl-2-pentene
2-methyl-1-pentene
3-methyl-2-pentene
1-hexene
12. _______ Which of the following is an acetal?
a) OH
OH
O
b)
c)
O
OH
O
d) OH
OH
O
13. ______ Which of the following is NOT a derivative of a carboxylic acid:
A.
B.
C.
D.
Methylethanoate
Acetic anhydride
N-ethylethanamide
Diethylether
14. ______ Which of the following reactions produces a compound that does
NOT contain a carbonyl:
A.
B.
C.
D.
Fischer Esterification
Williamson Ether Synthesis
Oxidation of a primary alcohol
Markovnikov addition of water to an alkyne
15. ______ Ethylene oxide is a(n):
A.
B.
C.
D.
Ether
Hetereocyclic compound
Epoxide
All of the above
16. Give the name of FOUR of the six plastics that are collected for recycling.
For each plastic, indicate whether the plastic is prepared by an addition
polymerization or a condensation polymerization.
1
2
3
4
5
6
–
–
–
–
–
–
poly(ethylene terephthalate) – condensation
high density polyethylene - addition
poly(vinyl chloride) - addition
low density polyethylene - addition
polypropylene - addition
polystyrene - addition
17. Name each of the following compounds:
O
NHCH 3
NO2
CH(CH 3)2
(Z)-3-ethyl-3-hepten-2-one
(1R,2S)-N-methyl-2-(1-methylethyl)-cyclopentamine
4-ethyl-3-methyl-5-nitro-1-hexyne
18. Conformations
•
Using Newman projections, draw the most stable conformation of 1chloro-2-methylpropane (along the C1—C2 bonding axis). Indicate why
this conformation is the most stable.
Cl
H
CH3
H
H
CH3
Staggered conformations are more stable than eclipsed conformations.
The Cl and the methyl groups will try to be as far away from each other as
possible. This means the Cl and one of the methyls will be anti.
•
Draw the most stable chair conformation of cis-1,2-dimethylcyclohexane.
Indicate why this conformation is the most stable.
19. For the compound provided below:
• Assign its R/S configuration
• Draw and label its enantiomer and assign its R/S configuration
• Draw and label one of its diastereomers and assign its R/S configuration
CH3
CH3
R
CH3
S
R
Cl
S
S
R
Cl
Cl
20. For each of the following terms, give a brief but explicit definition as
applied to organic chemistry. Also give an example for each.
Term
Chiral
compound
Organic Chemistry
Definition
molecule with 4
different groups
attached to a carbon
molecule that
contains bonds that
do not integer bond
orders
Meso compound compound with more
than one chiral center
but is not chiral
overall
Example
H
F
Cl
Br
Resonance
CH3
HO
H
HO
H
CH3
Nucleophile
Racemic
mixture
Lewis Base
e- pair donor
Equimolar mixture of
enantiomers
O
(±)-strychnine
21. Show how to prepare 1-methylcyclohexanol from cyclohexanol. (Hint:
more than one step is required!)
OH
O
H3C
OH
1) ether
K2Cr2O7
+ CH3MgBr
H2SO4
2) H3O+
22. Based on the IR spectrum below, provide a reasonable structure AND
NAME for unknown compound having a molecular formula: C4H6O2. Justify
your answer.
Acid O – H
stretch
C=O
stretch
sp3 C – H
stretch
C=C
stretch
23.
1.
Predict the major organic product for each of the reactions below:
3-penten-1-ol
K2Cr2O7/H2SO4 Æ
+
K2Cr2O7
OH
OH
H2SO4
O
OH
O
2.
3.
NaBH4
2-bromo-3-methylpentane
t-butoxide
Br
t-butoxide
4.
3-ethyl-1-hexene + H3O+ Æ
H3O+
OH
5.
OH
O
1) CH3CH2MgI
2) H3O
+
24.
(-)-Strychnine (structure shown below) can be found in the seeds of
Strychnos nuxvomica. It is commonly used in poison bait for rodents.
• Identify all functional groups in this
molecule.
*
arene, amide, amine, ether, and alkene
*
*
*
*
*
•
•
How many stereocenters does this
compound have?
6
What are three properties make this compound an “alkaloid”?
1) toxic
2) derived from plants
3) cyclic amine
•
The term “alkaloid” is derived from the word “alkaline”. What would
make this compound “alkaline”?
alkaline = basic
substituted, aliphatic amines are particularly basic
•
What does the (-) mean in the name “(-)-strychnine”?
(-) enantiomers bend plane-polarized light to the left
•
Is the structure shown the “free base” form or the “hydrochloride” form?
free-base, the structure is not a salt