2510_2023Sm_Pre1
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Course
2510
Subject
Chemistry
Date
Apr 3, 2024
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18
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CU ID (7 digit number)
Chemistry 2510
Cornell University
Summer 2023
Prelim 1
DO NOT OPEN THIS PRELIM UNTIL YOU ARE TOLD TO BEGIN.
Please write your answers directly on the question page.
All calculated values must be supported by work presented on the page in order to receive full
credit. Numerical answers should be presented with proper units.
You may find it helpful to read through the entire exam and work first on questions that are quick
and/or you are confident in. Once those are complete, you can return to the ones you find more
difficult.
Please follow the directions for each question and enclose answers in boxes where they are
provided.
The exam is printed double-sided and has 7 numbered questions on 10 pages. There is a separate,
colored double-sided packet with a periodic table, a ruler and information needed for several
problems.
Sign below to affirm that you are not presenting anybody else’s work as your own.
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2
Question 1
Finn Hudson struggles with headaches, so he always has Excedrin Extra Strength with
him. See colored sheets for relevant information.
a)
(8 pts) He wants to purify caffeine, so he grinds up 4 tablets and adds 25.0 mL of ethyl
acetate. After filtering out the insoluble material, he proceeds to add 15.0 mL of buffer (aq)
(pH ~7.5). Below, please indicate the probable location of each compound by drawing its
structure in the correct box (
pay attention to protonation state and formal charges
)
.
Assume
each compound only exists in one of the solvents.
b)
(6 pts) Finn believes that the three compounds are not separable by acid base extraction
because each of the three has an acidic proton (H). Is he correct? Explain briefly.
c)
(2 pts) If Finn obtained 0.421 g of caffeine, what was his percent recovery?
1c answer
Ethyl acetate layer
Buffer (aq) (pH ~7.5) layer
3
Question 2
Quinn Fabray wants to make aspirin from salicylic acid and finds a mixture of benzoic
acid and salicylic acid that the chemistry teacher had prepared for a recrystallization experiment
(like the one you did, except that salicylic acid was the target compound). She has a 1.5 g sample of
salicylic acid contaminated with an unknown amount of benzoic acid.
Compound
Solubility at 0°C (g/L)
Solubility at 100°C (g/L)
Benzoic Acid
1.7
68
Salicylic Acid
2.17
66.6
a)
(5 pts) What is the maximum theoretical percent recovery of salicylic acid?
b)
(5 pts) She gets distracted and accidentally adds 47.3 mL of boiling water to dissolve the
original sample. Rather than start over, she boils the sample until the volume is reduced to
1.3 mL, then cools it to 0°C. What mass of salicylic acid does she theoretically recover?
c)
(5 pts) Quinn repeats the procedure (correctly) and determines that she recovers 96% of the
1.5 g starting sample. From this she reasons that the starting sample is 4% salicylic acid. Is
her logic correct? Explain.
2b answer
2a answer
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4
Question 3
Rachel Berry is analyzing the salicylic acid that Robin purified.
a)
(4 pts) She measures the melting point of a small amount of the salicylic acid as 160-
161.5°C (lit: 159°C). Briefly explain the relevance of this result.
b)
(4 pts) Rachel runs a TLC of the salicylic acid and sees a vertical smear extending for half
the plate. What does this indicate about the purity of the compound, if anything?
c)
(4 pts) Sam Evans suggests that Rachel load less sample before running the TLC again. Is
this a reasonable suggestion? Why or why not?
d)
(4 pts) For a TLC of two unknown compounds, when the solvent front is 8.5 cm, the two
spots have R
F
values of 0.25 and 0.62. If the compounds are run again with a solvent front
of 6.0 cm, how far will each spot travel?
5
Question 3 (cont).
e)
(6 pts) Quickies…
i) When running a TLC plate should the lid be ON or OFF the sample chamber?
ii) How deep should the running solvent be relative to the sample origin?
iii) A nonpolar compound will have a LARGE or a SMALL R
F
?
iv) Increasing the polarity of the running solvent DECREASES or INCREASES the R
F
of a polar
compound?
v) How do you know when to stop running a TLC?
vi) Which will result in a lower R
F
for a very polar compound 50:50 or 10:90 ethyl acetate:hexanes?
f)
(4 pts) Puck purifies his reaction mixture by column chromatography after the synthesis
in question 4b. His grid TLC is shown below. On the analytical TLC, fill in a reasonable
approximation of expected results from the indicated fractions.
Fraction #:
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
Analytical TLC
Grid TLC of Fractions
1
2
3
4
5
TLC of Mixture
Before Column
Run Column Chromatography
6
7
8
9
10
6
Question 4:
Kurt Hummel is performing the oxidative cleavage reaction but, foolishly, he relies on
Sue Sylvester to provide the reagents. Instead of the expected diol, Sue gives him 2-methyl-1-
phenylhexane-1,2-diol. Mike uses 3.5 g of the diol and excess oxygen along with sufficient catalyst.
(See data on colored sheets.)
a)
(4 pts) What is the theoretical yield (in grams) for the synthesis of the benzaldehyde?
b)
(5 pts) Kurt runs a TLC and sees three spots by UV detection. One has the same RF as the
starting material. He states that this means that the side product was not formed. Do you
agree with Mike? Explain briefly.
4a answer
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7
Question 5:
To prepare for column chromatography of the reaction mixture from question 4,
Santana Lopez finds IRs of the 4 compounds of interest (the starting diol, the two products and the
possible side product). However, distracted by memories of dancing with Brittany Pierce, she fails
to label the printouts and mixes them in with her IRs from the other experiments. The IRs are in the
colored packet.
Please determine which IR correlates to each structure. Write the number of the corresponding IR
in the box next to the compound. (2 pts each)
OH
HO
O
O
O
HO
5a answer
5b answer
5c answer
5d answer
8
Question 6
Will Schuester finds a bottle labelled “magic voice potion”. Emma Pillsbury suggests
they perform some analysis on the compound to determine what it is. Using diethyl ether as the
organic solvent they measure the aqueous partition coefficient of the compound at various pHs (see
below).
pH
2
4
6
7
K
10.8
5.3
0.03
0.0006
a)
(3 pts) Is the compound an acid, a base or non-ionizable (neither an acid or base)? Explain
your answer.
b)
(3 pts) TLC indicates the presence of impurities, so they dissolve the compound in ethyl
ether. They want to wash out impurities and leave the compound in the ether. Should they
use a low pH or a high pH in the aqueous layer?
c)
(5 pts) Starting with 7.0 g of the compound in 25 mL of ether, they extract once with 10.0 mL
of pH = 6 buffer. What mass of the target compound remains in the ether layer?
d)
(5 pts) Unsatisfied with the results in part d, Emma performs a second extraction of the ethyl
ether layer. The bottle of buffer is running low so she only adds an additional 3.0 mL of
pH = 6 buffer. How much compound remains in the ether layer after the second extraction?
9
Question 7:
Dave Karofsky sets up the reflux apparatus below for the S
N
2 reaction, but Artie
Abrams is paying close attention. What 5 errors does Artie correct? Why do these errors need to be
corrected? (Explain briefly why the error is a safety or performance concern.)
1)
2)
3)
4)
5)
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10
DO NOT OPEN UNTIL TOLD TO BEGIN
Question 1 Data:
Back of a package of Excedrin Extra Strength
Basic nitrogen (pKa 0.7)
Acidic hydrogen
pKa 14
O
N
N
N
N
O
caffeine
H
O
OH
O
O
aspirin
Acidic hydrogen
pKa 2.97
O
N
H
OH
acetaminophen
Acidic hydrogen
pKa 9.5
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Question 4 Data:
Reactants
: 2-methyl-1-phenylhexane-1,2-diol
MW: 208.5 g/mol
Also, molecular oxygen and the catalyst
OH
HO
Expected Products
: O
O
Benzaldehyde
MW: 106.1 g/mol
hexan-2-one
MW: 100.1 g/mol
Possible side product
: O
HO
Question 5 IR Data:
IR #1
IR #2
Question 5 IR Data (cont):
IR #4
IR #3
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Question 5 IR Data (cont):
IR #6
IR #5
H
Be
1.008
9.012
1
4
Hydrogen
Beryllium Md
(258)
101
Mendelevium
No
(259)
102
Nobelium
Fm
(257)
100
Fermium
Es
(252)
99
Einsteinium
Cf
(251)
98
Californium
Bk
(247)
97
Berkelium
Cm
(247)
96
Curium
Am
(243)
95
Americium
Pu
(244)
94
Plutonium
N
p
(237)
93
Neptunium
U
238.0
92
Uranium
Pa
231.0
91
Protactinium
Th
232.0
90
Thorium
T
he
P
eriodic
T
able
of
e
lemenTs
Li
6.941
3
Lithium
He
4.003
2
Helium
B
10.81
5
Boron
C
12.01
6
Carbon
N
14.01
7
Nitrogen
O
16.00
8
Oxygen
F
19.00
9
Fluorine
M
g
24.31
12
Magnesium
Ca
40.08
20
Calcium
Sc
44.96
21
Scandium
Ti
47.87
22
Titanium
V
50.94
23
Vanadium
Cr
52.00
24
Chromium
Mn
54.94
25
Manganese
Fe
55.85
26
Iron
Co
58.93
27
Cobalt
Ni
58.69
28
Nickel
Cu
63.55
29
Copper
Zn
65.39
30
Zinc
Ga
69.72
31
Gallium
Na
22.99
11
Sodium
Rb
85.47
37
Rubidium
K
39.10
19
Potassium
Cs
132.9
55
Cesium
Fr
(223)
87
Francium
Al
26.98
13
Aluminum
Cd
112.4
48
Cadmium
A
g
107.9
47
Silver
Pd
106.4
46
Palladium
Rh
102.9
45
Rhodium
Ru
101.1
44
Ruthenium
Tc
(98)
43
Technetium
Mo
95.94
42
Molybdenum
Nb
92.91
41
Niobium
Zr
91.22
40
Zirconium
Y
88.91
39
Yttrium
Sr
87.62
38
Strontium
In
114.8
49
Indium
Tl
204.4
81
Thallium
H
g
200.6
80
Mercury
Au
197.0
79
Gold
Pt
195.1
78
Platinum
Ir
192.2
77
Iridium
Os
190.2
76
Osmium
Re
186.2
75
Rhenium
W
183.8
74
Tungsten
Ta
180.9
73
Tantalum
Hf
178.5
72
Hafnium
La
138.9
57
Lanthanum
Ba
137.3
56
Barium
Nh
(286)
113
Nihonium
Cn
(285)
112
Copernicium
Ce
140.1
58
Cerium
R
g
(282)
111
Roentgenium
Ds
(281)
110
Darmstadtium
Mt
(268)
109
Meitnerium
Hs
(277)
108
Hassium
Bh
(264)
107
Bohrium
S
g
(266)
106
Seaborgium
Db
(262)
105
Dubnium
Rf
(261)
104
Rutherfordium
Ac
(227)
89
Actinium
Ra
(226)
88
Radium
Fl
(289)
114
Flerovium
Mc
(290)
115
Moscovium
Yb
173.0
70
Ytterbium
Tm
168.9
69
Thulium
Er
167.3
68
Erbium
Ho
164.9
67
Holmium
Dy
162.5
66
Dysprosium
Tb
158.9
65
Terbium
Gd
157.3
64
Gadolinium
Eu
152.0
63
Europium
Sm
150.4
62
Samarium
Pm
(145)
61
Promethium
Nd
144.2
60
Neodymium
Pr
140.9
59
Praseodymium
Lv
(293)
116
Livermorium
Ts
(294)
117
Tennessine
Pb
207.2
82
Lead
Bi
209.0
83
Bismuth
Po
(209)
84
Polonium
At
(210)
85
Astatine
Sn
118.7
50
Tin
Sb
121.8
51
Antimony
Te
127.6
52
Tellurium
I
126.9
53
Iodine
Ge
72.63
32
Germanium
As
74.92
33
Arsenic
Se
78.96
34
Selenium
Br
79.90
35
Bromine
Si
28.09
14
Silicon
P
30.97
15
Phosphorus
S
32.07
16
Sulfur
Cl
35.45
17
Chlorine
Kr
83.80
36
Krypton
Xe
131.3
54
Xenon
Rn
(222)
86
Radon
Ar
39.95
18
Argon
Ne
20.18
10
Neon
O
g
(294)
118
Oganesson
Lu
175.0
71
Lutetium
Lr
(262)
103
Lawrencium
1A
2A
3B
4B
6B
8B
1B
2B
7B
5B
6A
3A
7A
5A
4A
8A
1
2
3
4
5
6
7
11
12
13
14
15
16
17
18
9
10
8
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