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CHEM 1152
Haseltine/Summer 2017
Exam #1
I. Multiple Choice (4 pts. each): select the best answer for each question.
1. How many moles of carbon dioxide are produced by the complete combustion of
one mole of ethylcyclobutane?
(a) 5.5
(b) 6
(c) 6.5
(d) 7
2. Exactly how many hydrogens are present in 2,3,3-trimethylhexane?
(a) 18
(b) 19
(c) 20
(d) 21
3. How many valence electrons are present in a neutral molecule of formula
C3H6O?
(a) 24
(b) 26
(c) 28
(d) 30
4. What is the proper IUPAC name of the following molecule?
(a) 1-butylcyclopropane
(b) 2-butylcyclopropane
(c) 2-cyclopropylbutane
(d) none of these answers
5. Which of the following can exist as cis or trans isomers?
(a) 2-methyl-1-butene
(c) 1-bromopropene
(b) cyclopentane
(d) 1,3-dibromopropane
6. What is the proper IUPAC name of the following molecule?
(a) 1-tert-butyl-4,4-dimethylhexane
(b) 2,2,6,6-tetramethylhexane
(c) 3,3,7,7-tetramethyloctane
(d) none of these answers
7. Which reaction of alkenes doesn’t give a mixture of syn and anti addition
modes?
(a) addition of H2O
(c) addition of Br2
(b) addition of HCl
(d) All of these do syn and anti.
8. Timberlake showed a figure comparing the packing of red and black licorice
sticks vs. tennis balls to illustrate how unbranched alkane molecules could
pack more closely and with more contact between individual molecules
than could branched alkanes. She was using this metaphor to explain the
known differences between unbranched and branched alkanes in their:
(a) boiling points.
(c) densities.
(b) water-solubilities.
(d) all of these answers
9. Which Lewis structure is correct for the neutral molecule H2NNH2?
a) H
H
N
H
b) H
N
H
N
H
H
c) H
H
N
N
H
H
d) H
N
H
N
H
H
10. Which of the following is a tertiary alcohol?
(a) cyclobutylmethanol
(c) 2,4-dimethyl-3-pentanol
(b) 1-ethylcyclopentanol (d) none of these
11. What is the molecular geometry at C3 in 1-butene?
(a) trig. planar (b) linear
(c) tetrahedral (d) bent
12. Which molecule is not a constitutional isomer of the others?
(a) 1-butyne
(c) cyclobutene
(b) 2-butyne
(d) cyclobutane
N
H
13. In a chair conformation of 1,3,5-tribromocyclohexane that has all three
bromo groups in equatorial positions, how many equatorial hydrogens are
present?
(a) 0
(b) 3
(c) 6
(d) more than 6
14. Which alkene cannot obey Markovnikov’s rule as it undergoes hydration?
(a) cyclooctene
(c) 1-hexene
(b) 2-methyl-2-butene
(d) 1-ethylcyclopentene
15. An aromatic compound that has an NH2 group directly attached to the ring
is a/an:
(a) toluene.
(b) phenol.
(c) anisole.
(d) aniline.
II. (16 pts.) Please give the major organic product for each reaction.
Show any expected cis or trans character as part of your answer.
Cl 2
HCl
H2
Ni cat.
OH
conc.
H 3PO 4
III. (10 pts.) Please draw five different cyclic constitutional isomers that
have the formula C5H9Br. Be careful not to draw the same structure
twice. If you draw more than five, circle the ones you want me to grade.
IV. (8 pts.) Please draw both possible chair conformations for trans1-bromo-3-fluorocyclohexane. Show all of the substituents at
carbons 1 and 3.
V. (6 pts.) Please draw each of the following as a bond-line structure,
showing any stereochemistry clearly.
(a) 1,3-propanediol
(b) cis-4-decene
(c) 1,2,4-tribromobenzene