Chemistry 106

First Exam
Februaryl T, 2014
N u,',',,
Q9
t!z'-\'''\''i7
Write your name on this sheet and on the Scantron ansrvcr sheet'
Write thc color of this paper on the Scantron sheet'
Only answers on the Scantron sheet will count'
Read each question carefully belore you ansn'er it'
Usc
your time u'isely' Answer the ones you can do easily, first'
Read the questions carefully. Answer the question asked!
Good Luck!
CI
C,'
Number correct Total Points
(Only your
best 33 will
be counted)
') *'
t-J
758
L The alcohol lbmred bl,fennenlation olfruil. grain, or potatoes
is
A. menthol
B. ethylene glycol
C. elhanol
D. methanol
2. which of the follou'ing compounds is most likely responsible for the odor of a skunk?
A. isoamyl acetate
B. ethylene glycol
3. Counl the number of stereocenlers in the following molecule and then calculate the ,ncLrimunl
number o/ possible srereoisonte,s. The maximum number of stereoisomers is:
A. t6 8.8 c.4
D.2
4. Menthol. shown here. is an example of a
6
ott lt ouo
lttn
tn'f-f-f-t-"
H OHH
A. primary alcobol
B. secondary alcohol
C. tertiary alcohol
D. phenol
C. cinnamaldehvde
o
D. 3-methylbutane- I +hiol
Itrc_.,zcltl
(\'
Y
CH:
5. Ethylene glycol, HOCH2CH2OH, commonly used as antifreeze, dissolves in the water in a car's
radiator by
A. a chemical reaction with water
C. London forces
N
.\
l)
C-l'
rrtr
. lI
'
\r
I I t'
,
av
,
-a
'\
L-,/
/_.
t
\
I
.
--R
U\
t
'l
u
6.
7.
NHCH
),
(/
D
O-*'O
Cr
c
B. solvated ions
D. forming hydrogen bonds to water
What is the IUPAC name of the following compound? [
{
cH.
ll
\'
1".
A.3-octanol
C. 3.5-dimethylhexanol
: I
t- -L
'.
"'ttfi""'[XfH'
B. 2,4-dimethyl-4-hexanol D. 3,5-dimethyl-3-hexanhl
. , . i
l:
\'.
Which of the following objects is chiral?
A. sock B. snail shell C. spoon D. pencil
8. Which of the following compounds is an aliphatic (not aromatic) amine?
t..
N
._)
13.
14.
15.
16.
Name the follbwing compound.
l'g
{i c-c-Y-
l:
t' tl
A. dibutylamine B. diisopropylamine C. propylamine
Identily the functional groups (X.Y, and Z) in the molecule of
vanillin shown here.
A. X = ketone, Y = ether, Z = alcohol
B. X= aldehyde, Y: ether, T = phenol
C. X = aldehvde. Y = ketone. Z: alcohol
D. X = carboxylic acid, Y: ketone,2 = phenol
I
11
clt. cHl
|'. I
CHr-C- N
-J-CIlr
-Tt
lt lt II
l
D. hexylamine
,r,,1-r,
rJ
B.
D-
A. alcohol
B. thiol
CH3CH2CH2CH2SH
D
4
/-',4.
Which statement best explains why amine drugs like benadryl or
Y
novocaine are often administered as their hydrochloride salts?
A. Increased solubility in wa1er.
B. Increased stability
(shelflife) because they are less likely to react with oxygen
C. Reduced toxicity
D. Both A and B
An unknown compound dissolves in aqueous HCl, but is insoluble in water, aqueous NaHCO:
and aqueous NaOH. Which of these compounds is it?
ctr"n'
'C.
aldehyde
D. amine
18. Which of the following compounds is the strongest acid?
A.
cH3cH2cH2cH2cH2cH2oH
c.
17. The following molecule contains which functional group?
CH3CH2CH2CH2NH2
c
c)-"'
CHTCHzOCHzCH3 CH3CH2CH2CH2OH
9. \\/hich ol'the lbllowing amines u'ill have the highcst boiling poinr?
Their molecular weights arc
-
)
the sanre or very similar. so thal is not a lactir.
'
*
\
--N'H
\
,
\
rcHrlrN cH3cH:NCH3
L__l
cHjcH2cH2NHz
'\.
\,
' \'\
A B C D
,, {*
'\'
t
\\
10. Which of the following compounds would be the major organic producr lormed in the following
dehvdration reaction? \
....-'.'%n-iruuglr
cH3cHcH2cH3
Too'
H
-?
-t^-i - c-- rr
5
'i
r
'#--- '
*'$"f,:;"
';
@,-l
;
4t
-c
='.'c,
c*t- =4cHz t)
A'
cHrcHCHrcH,
c CH3CH{HCH3
i
-i
-
1
ocHr
11-
C
-c=
4
'
+
,^r
B.
cH3ccH2cH3
D. H2c=cHcH2cHt
LH
7i
ll
:
c
tl Lll
f)
I l. Which of the following statements best explains why Vitamin A is less Soluble in water than 2-
propanol?
A. VitaminAisasolid
71.m1
B. Vitamin A cannot form hydrogen bonds
C. Vitamin A is not a salt
D. The alkyl portion of Vitamin A is too big to be brought into
solution by a single OH group
tJ
-L
-t
I
H
$
c-\
\'l
5
12. The following compormds are examples of
Ho..,--o
c'
:
H-C-OH
I
H-C-OH
CHrOH
o.
\6-oH
i
H'C-OH
I
Ho-9-H
CH2-OH
A,
B.
Vitahin A
identical molecules
enantiomers
retinol
C. diastereomers
D. ciVtrans isomers
26.
(S)-can onc. which tastcs like caraway seeds. has a speci'lic rotation of -62.5'. What is the
specific rolation of
(R)-can'one?
A. -125' B.
+62.5'- c:62.5'
D.
+5.25'
27. Which of the following compounds would be oblained if you mixcd the alcohol shoun belou'
with an oxidizing agent like K:CrrOr?
[O]
stands for the oxidation.
A
8-"
3
c
boJD 8""
(no reaction)
ofthe compound below?
14o
t
t('tu
' 'r'
11
Ho -H2C' t
alL
i
?' f',
Ho-Hrc-cirff,
H'""'Fcur-oH
AB
29. Which of the following statements best describes the colors
you would expect on the electrostatic
potential map of CHTCHzCHzCHzOH?
A. Oxygen red; hydroxyl H blue; methyl carbon
green
B. Oxygen blue; hydroxyl H red; methyl carbon green
C. Oxygen red; hydroxyl H red; methyl carbon blue
D. Oxygen
green; hydroxyl H yellow; methyl carbon blue
.)
r.
\(-""
bs
oH
cD
J
B""g
28. Which of the following compounds is NOT an enantiomer
OH
I
g..';C.-cHr-on
H:C
t\l
(lH
AA
,l.r'r-
'I
9. Which of thc follorving compounds is the enantiomer of
1S.;-2-pentanol?
'
A. (S)-3-pentanol
B.
(R)-2-pentanol
C. (e)-2-pentanol
D. trans-2-pentanol
20. Which of the follou'ing reagents is needed to carry out the follorving reaction?
."r.rr^t,
ll*C{
,
cuscu2RHr
+ cp
A. NaOH B_ HCI C.
O:
D.
NaHCO;
21. Which of the following compounds is the enantiomer of
A.
F..
-CH.
B.
Br r 9Hs
Br
A
iy
'",4"
c
,*+;,
D
H,c{,H
22. Which of the following amines will exist primarily (>99%)
in its protonated form in blood at a
pH of 7.4?
D-
23. (S)-cawone has a specific rotation of-62.5". A racemic mixture ofthe R and S carvone
enantiomers will have a rotation of
A. 00 B. -62.5" C.+62.5" D. -125.
24. Which of the following compounds cannot form hydrogen bonds to water?
c.
25. Which ofthe following statements best describes hydrogen bonds.
A. They are intermolecular forces.
B. They are weaker than covalent bonds
C. They are possible when a molecule contains an N-H or O-H group
D. All of these statements
a
U(
ns4 ,u
?
CH:
GJ
I
H
NH,
x
lil
\-,,/
B.
o
A.
)
d
D.
HO
d
o
H
I
AOB
34. Chirality is important in living systems because
A.En4mesareproteinsrvithspecificallyshapcdactivesitessothcl.onl-vreaclu.iththc
proper comPound.
B. The protein nrolecules that interact
with srnall molecules
and send messages
to the brain
about scint or taste have chiral binding sites to give them specificity'
c. The biomolecules
to u,hich chemical messenger
molecules like serotonin
or adrenaline
bind are chiral so they only respond to the right compounds'
D. All of these.
35. when globular proteins in water fold into their active conformations,
the specific
side chains on
amino acids make some of them more likely 1o end up on the outside of the molecule'
facing
theaqueous(water)environment,whileothersaremorelikelytobefoundorrtlreinsideof
the
protein, a*uy from the water' Which of the following
amino acids- would be most likely
,o
"la
up on the outside of the progt4;lacing the water? The name of the amino acid and the
slructure of its side chain arb giv.-fn'
A. phenylalanine
C. serine
HOCH:-
D. cysteine
HSCH2-
*t
EFCH,_
B. alanine
cHr-
36. Which of the following statements about chiral drugs is FALSE?
A. The correct stereoisomer
of a chiral drug is most effective'
B. Drugs tlat are chiral are always sold and administered as a single enantiomer'
'
-C. The enantiomer ofa chiral drug can have very different effects and can be very
dangerous.
D. The enantiomeric
form of some chiral drugs is harmless and
just
makes it less effective'
30- In a'l'V ad lor thc Rcd l,obsler chaitt oftcstauranls.
thc announccr
savs.
"\\ihcn
Iilc gircs
1ou
a
I lcnlon. squeeze it on lobsler." Which ol'the fblloning besr explains tlre benefirs (cherricallr.
spr:aking) of squeczing lemon orr
1.our
lobster.
A. The limonene in thc lenron goes rvell u,ith the lishl, lastc ol.lobstcr.
B' The- lirnonene in lhe lenron reacts uilh the anrines in the lobstcr 1o make the lobsler
more lender.
C. l'he citric acid in lemon reacts with amines in lobster. removing the fishy taste and snrell
bccause the resulting ammonium sah is not volatile.
D. The citric acid in lcnon reacts u'ith amines in lobstcr. removing the fishy taste and smell
because the resulting compound does not dissolve in u,a1er.
31. Chose the answer that best explains the chemical reason that methanethiol,
CHrSIl. has a lower
boiling point (6'c)
than methanol (65"c)
even though it has a much higher molecular
weight.
A. Methanol can form hydrogen bonds to waler.
B. The alcohol can form hydrogen bonds between the O of one molecule and the hydroxyl H
of another; sulfur cannot do this.
C. The covalenl S-H bond in the thiol is weaker than the covalent O-H bond in the alcohol.
D. Methanthiol is a gas at room temperature.
32. Which of the following compounds is the major organic product of the following reaction?
^d^
*
B
rl
'-
/
)attro"
-.,-,..i
I
t
H:so,r
iY"
Y\"
t)
33- Which of the following reagents would you choose to distinguish between t}1e following two
compounds by a solubiliry test?
o
,..t-\-
tt
c
^#
\._/
A. 5%HCl B. 5%NaHCO3
C. S%NaOH D. H,O