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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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4 14)
Based on the IR and proton NMR below, determine the structure of the compound with molecular formula C
4
H
9
NO. Calculate the DU. At the bottom of each peak is a letter. Label the hydrogen in your structure with the letters corresponding to their peaks. Label all important peaks in the IR. Show all work for partial credit. (20 pts.)
DU = [(4 x 2) + 2 – 9 + 1]/2 = 1 from C=O peak in IR; C=O peak in IR is in the range of amide functional group Peak a, the broad singlet, is the NH
2
group; Peak b is a CH with multiple neighbors; Peak c are two equivalent CH
3
’s next to a CH 1 1 6, d a b C=O Csp
3
-H Carboxylic acid 4000 3000 wavenumber cm
-1
2000 1500 1000 500 2 broad singlet 1 6, d a b NH
2
Csp
3
- H C=O
5 15)
Based on the IR and 13
C NMR below, determine the structure of the compound with molecular formula C
4
H
6
O. Calculate the DU. At the bottom of each peak is a letter. Label the hydrogen in your structure with the letters corresponding to their peaks. Label all important peaks in the IR. Show all work for partial credit. (20 pts.)
DU = [(4 x 2) + 2 – 6]/2 = 2, comes from triple bond because triple bond peak in IR. Peak at 3300 cm
-1
indicates triple bond is terminal C
≡
C bond. No C=O peak or O-H peak means oxygen functional group is an ether. NMR peaks a and b must be groups next to O. Peaks a and c are only peaks that can correspond to triple bond (can’t have triple bond carbon with more than 1 H). Leaves other side of ether as ethyl group from peaks b and d. 4000 3000 wavenumber cm
-1
2000 1500 1000 500 C CH
2
CH CH
3
a b c d ignore these peaks Csp
3
- H Csp- H C
≡
C
6 16)
Based on the proton NMR below, provide a structure for the following molecular formula: C
6
H
12
O
2
. Calculate the DU.Label each peak in the spectrum with a letter and label the corresponding hydrogen in your structure with the appropriate letter. (15 pts.)
DU = [(6 x 2) + 2 – 12]/2 = 1; peak a is CH
3
with no neighbors and C bonded to O (3.7 ppm); peak b CH with many neighbors, peak c CH
2
with many neighbors; peak d CH
3
next to CH; peak e CH
3 next to CH
2
; accounts for 5 carbons, sixth carbon must be C=O 17)
Based on the carbon NMR below, provide a structure for the following molecular formula: C
8
H
7
ClO. Calculate the DU. At the bottom of each peak is a letter. Label the carbon in your structure with the letters corresponding to their peaks. (17 pts.)
DU = [(8 x 2) + 2 – 7 – 1]/2 = 5 indicates benzene ring, confirmed by 2 peaks between 7 and 8 (b and c); benzene peaks integrate to 4, so benzene has two substituents. Two doublets each integrating to 2 indicates the substituents will be opposite each other. Peak at 10 (a) is from an aldehyde hydrogen and singlet means it has no neighbors. Peak d indicates there is a CH
2
group with no neighbors and chemical shift indicates it is next to Cl. 3 2, m 1, m 3, d 3, t a b c d e 2, s 2, d 2, d 1, s a b c d
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Related Documents
Related Questions
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
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
Consider the molecules
— BrF5.
A. Draw the best Lewis structure for this molecule. Label any atoms with nonzero formal charge.
B. Label each bond angle. As part of your answer be sure to include if it is more or less than the ideal bond angle.
C. What is the electron geometry around the bromine atom?
D. Are the bonds in the molecule polar?
E. Is the overall molecule polar?
— CH2 F2 .
A. Draw the best Lewis structure for this molecule.
B. Label each bond angle. Answers for A-D here:
C. Redraw the shape of the molecule. Draw all dipoles.
D. Is the overall molecule polar?
— Consider the molecule CH2 CF2 .
A. Draw the best Lewis structure for this molecule.
B. Label each bond angle.
C. Redraw the shape of the molecule (according to the exacting specifications of your instructor). Draw all dipoles.
D. Is the overall molecule polar?
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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
Draw the Lewis structure for CO.
A. Calculate the formal charge on each atom in CO.
B. Draw the dipole for CO.
C. Calculate the oxidation numbers for the carbon and oxygen atoms in CO.
D. Formal charges, dipoles, and oxidation numbers are different ways of understanding the charges on covalently-bonded atoms. They tend to agree or be similar. At least in some ways, they disagree for CO. Formal charge guidelines assume that all bonding electrons are shared evenly between the two bonded atoms. Oxidation number guidelines assume that the more electronegative atom in the bond gets all of the electrons. Dipole theory assumes that the bonded electrons are associated more with the more electronegative atom. Now that you understand the basis for the oxidation number guidelines, determine the oxidation number for each carbon in propane assuming that the more electronegative atom gets all of the bonded electrons. You will need to draw the Lewis structure of propane for your answer.
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
Р
ed Lewis structure
H-CC-H
[H_H_O_H]*
Η
N_0_a:
Is the proposed Lewis structure reasonable?
Yes.
No, it has the wrong number of valence electrons.
The correct number is:
No, it has the right number of valence electrons but doesn't satisfy the
octet rule.
The symbols of the problem atoms are:*
Yes.
No, it has the wrong number of valence electrons.
The correct number is:
No, it has the right number of valence electrons but doesn't satisfy the
octet rule.
The symbols of the problem atoms are:*
Yes.
No, it has the wrong number of valence electrons.
The correct number is:
No, it has the right number of valence electrons but doesn't satisfy the
octet rule.
The symbols of the problem atoms are:*
arrow_forward
Fill in the table. Central atom is listed first. A. Write the number of valence electrons below the formulaB. Draw the Lewis structureC & D. Write the Electron Group Geometry and Molecular Shape NamesE. Write the bond angleF. Write the molecular polarity. "P" for polar and "NP" for nonpolar.
SpeciesValenceElectrons(1 pt.)
LewisStructure(2 pt.)
Electron PairGeometryName(1 pt.)
Molecular ShapeName (1 pts.)
BondAngle (1 pt.)
Molecular Polarity(1 pt.)
PO43-
NOBr
Upload
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?
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2. Draw the lewis structures for both resonance structures of the OCBr+ ion and select the statement that is true
a. The molecule sometimes looks like one resonances structure, and at other times it looks like the other resonance structure
b. In one resonance structure, the carbon is in the center, and in the other one, the oxygen is in the center
c. The bond between carbon and oxygen would best be described as 2.5 bonds (halfway between a double and a triple bond)
d. In one resonance structure the positive charge is on the bromine, and in the other, it is on the carbon.
arrow_forward
4. CHCl3
a.
Lewis structure
Electronic geometry_
C.
d. Molecular shape_
e. Bond angle?
b. Draw the different bonds and label
their polarity.
inorpelt b
Soigns broff
02 8
arrow_forward
Draw the Lewis structure for the molecule, AX3, where A has 5 valence electrons and X (which is more electronegative than A) has 7 valence electrons. Which choice correctly describes the Lewis structure?
a) the structure has three A—X single bonds and one lone pair of electrons on A
b) the structure has two A—X single bonds, one A=X double bond, and no lone pairs of electrons on A
c) the structure has two A—X single bonds, one A=X double bond, and one lone pair of electrons on A
d) the structure has three A—X single bonds and two lone pairs of electrons on A
e) the structure has three A—X single bonds and no lone pairs of electrons on A
arrow_forward
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Related Questions
- 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_forward2. 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_forwardb. There is one additional resonance structure. NH₂ c. There is a total of five resonance structures (including the original structure). : OHarrow_forward
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