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1 CHEM 213 Organic Chemistry Spring 2024 Exam 1 Answer Key 1)
Why do C
≡
C bonds vibrate at a higher frequency than C=C bonds? a.
The triple bond is the stronger “spring” due to its stronger bond. b.
Since the C
≡
C atoms are bonded to less atoms, they have a smaller mass than the C=C atoms. c.
Vibrations break the
bonds and the triple bond wants to be broken less than the double bond. d.
Actually, C=C bonds vibrate at a higher frequency. 2)
The peaks in an infrared spectrum correspond to… a.
…the IR lightwaves that cause the molecule to slow down. b.
…the IR lightwaves transmitted by the sample. c.
…the IR lightwaves with frequencies that match vibrations in the molecule. d.
IR lightwaves have nothing to do with the peaks. 3)
What IR absorption bands are consistent with this structure? a. …3400, 3050, 2900 cm
-1
b. …2900, 1650, 3400 cm
-1
c. …3400, 1650, 1600 cm
-1
d. …3400, 2900, 2250 cm
-1
4)
B
eff
, the magnetic field felt by a nucleus, is determined by… a. … only the applied magnetic field. b. … the applied magnetic field plus electron shielding. c. … the applied magnetic field, electron shielding and any nearby magnetic fields, such as the magnetic field induced by benzene ring current. d. … the applied magnetic field, electron shielding, nearby magnetic fields and the vibrations of the nucleus 5)
13
C NMR can tell you… a. …about functional groups present and how shielded some carbons are. b. …the number of non-equivalent carbons in the molecule. c. …whether or not your compound has an alkyl ring. d. …all of the above. e. …only a and b. f. …only a and c. 6)
How many carbon atoms does a molecule contain if in its mass spectrum the relative abundance of the M+ peak is 50.1% and of the M+1 peak is 5.5%. a. 10
b. 9 c. 8 d. 7
2 7)
List 4 of the 5 non-fingerprint region IR peaks (
range and vibration
) you expect to see for the following molecule. (16 pts.)
a. C
≡
N, 2260-2210 cm
-1
c. Csp
3
-H, 3000-2800 cm
-1
b. C=C, 1620-1680 cm
-1
d. Csp
2
-H, 3100-3000 cm
-1
e. O-H, 3600-3200 cm
-1
8)
For each of the following compounds below tell how many signals you would expect the molecule to have in its proton NMR specturm (ignoring splitting) (12 pts.)
9)
Predict the splitting patterns for the protons indicated by the arrow. (12 pts.)
quartet singlet triplet of triplets triplet 10)
For each of the compounds below tell how many signals you would expect the molecule to have in its normal, broadband decoupled 13
C NMR spectra. (6 pts.)
3 11)
Rank (1-4) the chemical shifts of the indicated hydrogens from highest
(1) to lowest
(4). (8 pts.)
12)
Label all non-fingerprint peaks in the IR below. Based on these peaks, make a separate list of the functional group(s) most likely in the molecule that made this spectrum. (10 pts.)
Possible functional groups: alcohol, alkene 13)
Provide a molecular formula for the compound with the following mass spectrum. (8 pts.)
77 112 114 C
6
H
5
Cl 3:1 ratio of M+ peak and M+2 peak indicates Cl (35 amu) 112 – 35 = 77 (benzene cation peak) Rule of 13: 77/13 = 5.9 ~ 6 12 x 6 = 72 77 – 72 = 5 = # of H’s ignore this peak O-H Csp
3
-H C=C Csp
2
-H
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Related Questions
5. The reason there is danger in exposure to high-energy radiation (e.g., ultraviolet and X rays)
is that the radiation can rupture chemical bonds. In some cases, cancer can be caused it. A
carbon-carbon single bond has a bond energy of approximately 348 kJ per mole. What
wavelength of light is required to provide sufficient energy to break the C-C bond? In which
region of the electromagnetic spectrum is this wavelength located?
arrow_forward
A mixture of Hz and Clz is stable, but a bright flash of light passing through it can cause the mixture to explode. The light causes Cl2
molecules to split into Cl atoms, which are highly reactive. What wavelength of light, in nm, is necessary to cause the Cl2 molecules to
split? The bond energy of Clz is 242.6 kJ/mole.
Part 1
Your answer is correct.
Calculate the energy, in J, needed to break 1 Cl-CI bond if it takes 242.6 kJ to break a mole of Cl-CI bonds.
Enter your response in scientific notation as 1.00e-10, for example.
40.3e-20
eTextbook and Media
Hint
Attempts: 2 of 15 used
Part 2
Your answer is incorrect.
What frequency of light is necessary to cause the Clz molecules to split?
Enter your response in scientific notation as 1.00e-10, for example.
arrow_forward
Answer the following questions about compound
a. Label the shortest C–C single bond.
b. Label the longest C–C single bond.
c. Considering all the bonds, label the shortest C–C bond.
d. Label the weakest C–C bond.
e.Label the strongest C–H bond.
f.Explain why bond [1] and bond [2] are different in length, even though they are both C–C single bonds.
arrow_forward
6,7,8,9,10 Letters ONLY
arrow_forward
2. The Lewis structure for the acetate ion [C₂H3O2]¹ is given below:
le
a. Read section 1.9. What is the geometry (shape) around each of the carbon atoms
in the acetate ion - tetrahedral, trigonal planar or linear?
b. Each of the oxygen atoms in the acetate ion have an octet. Draw all lone pairs of
electrons in the acetate ion given above.
c. Read section 1.7. Use electron pushing to generate a resonance structure of the
acetate Lewis structure given above.
arrow_forward
b. There is one additional resonance structure.
NH₂
c. There is a total of five resonance structures (including the original structure).
: OH
arrow_forward
APTER 8 CHAPTER ASSESSMENT
Covalent Bonding
Reviewing Vocabulary
Match the definition in Column A with the term in Column B.
Column A
Column B
1. The tendency of an atom in a compound to attract electrons
I 2. A kind of bond in which there is unequal sharing of electrons
a. structural formula
b. molecule
3. Any bond in which there is electron sharing
c. VSEPR model
4. The particle formed when two or more atoms bond covalently
d. coordinate covalent bond
5. Reactions that occur when more energy is released forming new
e. hybridization
bonds than is required to break bonds in the initial reactants
f. oxyacid
6. A kind of bond in which electrons are shared in an area centered
between the two atoms
g. electronegativity
7. A kind of bond formed by overlap of parallel orbitals
h. sigma bond
8. Any acidic compound that contains oxygen
i. polar covalent
j. pi bond
9. A model that shows how the atoms are arranged in a molecule
k. covalent bond
m.
10. Reactions that occur when more energy is…
arrow_forward
2. Use the table below to estimate AH for the
reaction NO + O3 → NO2 + O2. Does this
reaction consume or produce heat?
Single Bond Energies (kJ/mol of bonds)
н сN oS F C Br I
Н 436
C 413 346
N 391 305 163
O 463 358 201 146
S 347 272
226
-
F 565 485 283 190 284 155
Cl 432 339 192 218 255 253 242
Br 366 285
201 217 249 216 193
-
I 299 213
201
278 208 175 151
-
-
Multiple Bond Energies (kJ/mol of bonds)
C=C 602
C=N 615
C=O 799
C=C 835
CEN 887
C=O 1072
N=N 418
N=O 607
N=N 945
O=O 498
arrow_forward
Chemistry
Organize the following three molecules in order of increasing stability in water (least
>
arrow_forward
2. Avogadro does not "waste" his time drawing a Lewis structure before
determining the shape of PF3. He thinks that the shape of PF3 must be trigonal
planar because there are three fluorine atoms bonded to the central
phosphorus atom.
a. Draw the Lewis structure for PF3.
b. Was Avogadro's answer for the shape of a PF3 molecule correct? Explain
c. Why is it important to draw the Lewis structure for a molecule before
identifying the shape of the molecule?
3. Draw the Lewis structure of ozone, O3. Describe why ozone has a bent shape
instead of a linear shape.
arrow_forward
How much energy (in kJ) is required to separate (break) one mole of H-H bonds?
Bond
Length (pm) Energy (kJ/mol)
H-H
74
436
H-C
106.8
413
H-N
101.5
391
H-O
97.5
467
O A) +436 kJ
B) -436 kJ
O C) +74 kJ
D) -74 kJ
E) 106.8 kJ
arrow_forward
Given the table of bond energies, which of the following is an accurate comparison of the energetics of breaking bonds?
H-H 436
H-F 569
H-CI 432
H-Br 366
H-I 298
C-H 410
C-c 350
CIN 300
C10 350
C-F 450
CICI 330
C-Br 270
CII
240
Table of Average Bond Energies (kJ/mole)
N-H 390
NIN
240
N-F
270
N CI 200
N-Br 240
N1O 200
O-H
460
O O
142
O -F 180
O -CI 200
220
✓
F-F 157
F-Cl
251
F-Br
234
Cl-Cl
Cl-Br
243
219
Br-Br 194
1-1
153
179
1-Br
I-CI 208
280
1-F
C=C
C=0
CIN
C=S
010
498
N=N 418
N=0
607
C C
C=O
C=N
NEN
611
745
615
477
835
1077
891
941
It is harder to break a C-C single bond than a C=C double bond because breaking the single bond releases more energy.
It is harder to break a C-C double bond than a C-C single bond because breaking the double bond requires more energy.
It is harder to break a C-C single bond than a C=C double bond because breaking the single bond requires more energy.
It is harder to break a C=C double bond than a C-C single bond because breaking the double bond releases…
arrow_forward
Given the table of bond energies, which of the following is an accurate comparison of the energetics of breaking bonds?
H-H 436
H-F 569
H-CI 432
H-Br 366
H-I
298
C-H 410
C-C 350
CIN 300
C10 350
C-F
450
C-Cl 330
C-Br 270
CII
240
Table of Average Bond Energies (kJ/mole)
N-H 390
NIN
240
N-F
270
N_CI 200
N-Br 240
N1O 200
0 H
010
0-F
O -CI
O -1
460
142
180
200
220
Y
F-F 157
F-Cl
251
F-Br 234
CI-CI
243
Cl-Br 219
Br-Br
1-1
1-Br
I-CI
I-F
194
153
179
208
280
C=C
C=0
C=N
C=S
010
N=N
N=O
C C
C=O
CEN
NEN
611
745
615
477
498
418
607
835
1077
891
941
It is harder to break a C-C single bond than a C=C double bond because breaking the single bond releases more energy.
It is harder to break a C-C double bond than a C-C single bond because breaking the double bond requires more energy.
It is harder to break a C-C single bond than a C=C double bond because breaking the single bond requires more energy.
It is harder to break a C=C double bond than a C-C single bond because breaking the double bond…
arrow_forward
1. How can you tell if a compound is covalent?
2. What distinguishes a covalent bond from an ionic bond?
3. How do you know how many valence electrons an atom has?
4. What is electronegativity? Is electronegativity a property of atoms or bonds?
5. What is polarity? Is polarity a property of atoms or bonds?
6. Describe in detail the N-F bond in terms of the relevant electronegativities and polarities.
7. What does VSEPR stand for and how does it allow one to predict the shapes of covalent molecules?
arrow_forward
SEE MORE QUESTIONS
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Related Questions
- 5. The reason there is danger in exposure to high-energy radiation (e.g., ultraviolet and X rays) is that the radiation can rupture chemical bonds. In some cases, cancer can be caused it. A carbon-carbon single bond has a bond energy of approximately 348 kJ per mole. What wavelength of light is required to provide sufficient energy to break the C-C bond? In which region of the electromagnetic spectrum is this wavelength located?arrow_forwardA mixture of Hz and Clz is stable, but a bright flash of light passing through it can cause the mixture to explode. The light causes Cl2 molecules to split into Cl atoms, which are highly reactive. What wavelength of light, in nm, is necessary to cause the Cl2 molecules to split? The bond energy of Clz is 242.6 kJ/mole. Part 1 Your answer is correct. Calculate the energy, in J, needed to break 1 Cl-CI bond if it takes 242.6 kJ to break a mole of Cl-CI bonds. Enter your response in scientific notation as 1.00e-10, for example. 40.3e-20 eTextbook and Media Hint Attempts: 2 of 15 used Part 2 Your answer is incorrect. What frequency of light is necessary to cause the Clz molecules to split? Enter your response in scientific notation as 1.00e-10, for example.arrow_forwardAnswer the following questions about compound a. Label the shortest C–C single bond. b. Label the longest C–C single bond. c. Considering all the bonds, label the shortest C–C bond. d. Label the weakest C–C bond. e.Label the strongest C–H bond. f.Explain why bond [1] and bond [2] are different in length, even though they are both C–C single bonds.arrow_forward
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