Chemistry 1506 Practice Exam 1
Youngstown State University
Department of Chemistry
Chemistry 1506
Practice Exam 1
25 Questions, 4 points each
1. What is the correct IUPAC name for the following compound?
CH 2 CH 2CH 3
CH 3 C CH 3
CH 3
(a) 2-methylisopentane (b) 2,2,-dimethylisopentane (c) 2,2,-dimethylpentane (d) t-butylpropane
2. Which structure corresponds to the name 1,4-diethylcyclohexane?
(a)
(b)
CH 2 CH 2
CH 3 CH 2 CH
CH 3CH 2
CH
CH CH 2CH 3
(d)
CH 3 CH 2
CH
CH 3CH 2
CH 2
CH 2
CH 2
CH 2 CH 2
1,4-diethylcyclohexane
CH
CH
CH 2
CH 2 CH 2
(c)
CH 2CH 3
CH 2
CH
CH 2
CH CH 2CH 3
CH 2
CH 2
CH 2 CH 2
CH 3 CH 2
3. How many O2 molecules are required to balance the complete oxidation of cyclobutane as shown
below?
CH 2 CH 2
+
(a) 2
CO 2
O2
CH 2 CH 2
(b) 4
(c) 6
+
H 2O
(d) 8
4. How many geometric isomers are possible for the compound whose formula is C2H2Cl2, one of
which is shown below?
Cl
C CH 2
Cl
(a) 1
(b) 2
(c) 3
(d) 4
5. Saturated hydrocarbons undergo what reaction in biological systems?
(a) bromination
(b) oxidation
(c) hydration
(d) none
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Chemistry 1506 Practice Exam 1
6. Which name is correct?
(a) 2,3-dibromocyclobutane
(c) 1,2-dimethylcyclopropane
(b) 1,4-diethylcyclobutane
(d) 4,5,6-trichlorocyclohexane
7. Which structure is incorrect?
(a)
CH 3
CH 3 CH
(c)
Br
CH 2 CH 2
CH 3
CH 3CH 2
(b)
CH 2 CH 3
Br
H
CH 3CH 2 C CH 3
Br
(d)
Br
Br
CH 3CHCH 2 C CH 3
Br
8. When writing the C=C, both bonds appear the same, however we know in fact that:
(a) there is free rotation around it.
(c) one is a σ bond and the other is a π bond
(b) one is straight and the other is bent.
(d) they are both p bonds.
9. If water were added to the olefin below, in dilute H+, what would be the name of the major product?
CH 3 CH 2
C CHCH 3
+
(a) 2-ethyl-3-pentanol
(b) 2-ethyl-2-pentanol
(c) 3-ethyl-2-pentanol
(d) 3-ethyl-3-pentanol
H 2O
CH 3 CH 2
10. What would be the name of the hydrocarbon resulting from the addition of H2 (over Ni) to the
following olefin?
CH
CH 3 CH
CH
CHCH 3
+
H2
CH 2 CH 2
(a) 2,4-dimethylcyclohexane
(b) 1,5-dimethylcyclohexane
(c) 3,6-dimethylcyclohexane
(d) 1,4-dimethylcyclohexane
11. What is the IUPAC name of the following olefin?
CH 3CH 2 CH
CHCHCH 2 CH 3
Br
(a) 3-bromo-5-heptene
(b) 5-bromo-3-heptene
(c) 3-bromo-4-heptene
(d) 4-bromo-3-heptene
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Chemistry 1506 Practice Exam 1
12. Which of the following formulas corresponds to cis-3-octene?
(b)
(a)
CH 3CH 2
CH 2CH 2CH 3
CH 3CH 2 CH 2
C C
H
H
C C
H
H
CH 2CH 2CH 3
(d)
(c)
CH 3CH 2 CH 2CH 2
CH 3CH 2
CH 2CH 3
C C
H
C C
H
H
H
CH 2CH 2CH 2 CH 3
13. Which of the following is a secondary (2o) alcohol?
(a)
(b)
CH 3CH 2 OH
CH 3CH 2 CHCH 2 CH 3
(c)
CH
(d)
CH 3CHCH 2OH
CH
CH 3
OH
CH
CH
C OH
CH
14. Name the product of the following reaction.
(a) 1-propanol
(b) 2-propanol
(c) 1-butanol
(d) 2-butanol
H+
CH 3CH 2 CH CH 2
+
H 2O
15. What product would result from the oxidation of cyclohexanol (below).
CH 2 CH 2
CH 2
(a)
(b)
(c)
(d)
[O]
CH OH
CH 2 CH 2
cyclohexene
cyclohexane
cyclohexanone
cyclohexanal
16. Which compound would fail to react with oxidizing agents MnO4- and Cr2O72-?
OH
(a)
CH 3OH
(b)
CH 3CH 2OH
(c)
CH 3CHCH 3
OH
(d)
CH 3 CCH 3
CH 3
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Chemistry 1506 Practice Exam 1
17. Choose whether 2-methyl-2-pentanol is 1o, 2o, 3o, or 4o.
OH
CH 3CH 2CH 2 CCH 3
(a) 1o
CH 3
(b) 2o
(c) 3o
(d) 4o
18. What product (if any) would result from the oxidation of 2-methyl-2-hexanol?
(a) 2-methyl-2-hexanone
(b) 2-methyl-2-hexanal
(c) 2-methyl-2-hexene
(d) No Reaction
19. What is the organic product of a reaction of ethanal with Tollen’s reagent (Ag+/OH-/NH3)?
[Ag metal forms a silver mirror as Ag+ is reduced].
O
O
(a)
(b)
CH 3C
O
(c)
CH 3C
CH 3C
OH
H
O
-
(d)
No Reaction
20. What is the organic product of a reaction of acetone (2-propanone) with Benedict’s reagent
(Cu2+/OH-)?
OH OH
O
OH
(a)
CH 3 CHCH 3
(b)
CH 3 CCH 3
(c)
CH 3 CH
CH 2
(d)
No Reaction
21. To convert ethanal to ethanol, one must do a(an) (type of reaction)?
(a) oxidation
(b) reduction
(c) addition
(d) condensation
22. What aldehyde and alcohol were used to form the following hemiacetal?
(a)
(b)
(e)
(f)
OH
CH 3 CH
OCH 3
acetaldehyde and methanol
acetaldehyde and ethanol
formaldehyde and methanol
formaldehyde and ethanol
23. What reaction would lead to the following product?
OH
O
CH 3CH 2C CHC
H
H CH 3
(a)
(b)
(c)
(d)
oxidation of 1-hexanol
reduction of 3-hexanone
aldol condensation of propanal
ketal condensation
24. What is the molecular formula of glycerol, 1,2,3-trihydroxypropane?
(a) C3H6O3
(b) C3H8O3
(c) C3H9O3
(d) C3H10O3
25. How many carbon atoms are there in a molecule of 1,2,5-triisopropylcyclohexane?
(a) 9
(b) 12
(c) 15
(d) 18
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