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|. Which of the following is NOT a basic component of a mass spectrometer?
Choose one ‘Aion source
answer. 8, mass analyzer
detector
D. difraction grating
|. The most abundant ion in a mass spectra, which is assigned a relative abundance of 100, is referred to as the
CChoase one A Base peak
answer, 8, Reference peak
. Detection tit
D. Blank corelation
The mass spectra of fluorine
Choose one 2:15 similar to te spectra of bromine and chlorine
answer, b. Consists of only one peak, since its moncisotopic
Consists of two peaks, separated by two Da
4. Consists of two peaks, appearing at 19 Da and 38 Da
The five peaks ina mass spectrum of chlorine can be attributed to
Cchoose one 2. Loss of electrons
answer. », ts oxidative abiity
The presence of two abundant isotopes
4. All of the above
CCalbration ofa mass spectrometer Is
Choose one 2, Performed externaly, with @ known sample measured independently
answer. b. Performed internally, with a known sample that is premixed with the unknawn
«. Unnecessary because the mass detector is highly stable
4. Both a and b are correct; calibration can be internal or external
The xeaxis ofa mass spectrum typlelly reports
Choose one 2 Mass to charge (m/z) ratios
answer. ». Parts per milion (ppm)
« Wavenumbers (em)
4. Wavelength (nm)
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Iva mass spectra contains peaks at 35 and 37 Da,
Choose one {. it most kely contains chlorine
answer. b. it can be identified as RbBr
«twas analyzed in a gas matrix containing argon
4. itwas analyzed in a gas matrix containing krypton
|. MALDI and ESI are
CChoose one _2. Ionization methods commonly used for biochemical analysis
answer, b, Detection methods used for spectral fingerprinting
«. Separation methods used prior to MS analysis
«Mass analysis techniques requiring external calibration
Tandern rass spectrometers
Choose one ‘2. Contain two or more mass analyzers
answer, , Can be used for structural studies
6. Can be used for sequencing studies
4. All of the above
The molecular ion (M+)
Cchoose one 2a. the highest molecular weight peek observed ina spectrum
answer, b, Has an assigned relative abundance of 100,
Represents the parent molecule minus an electron
4. Both a and ¢ are correct
Due to structural stably, the moleculi lon peaks are strong in mass spectra of,
Choose one a. akeohols
answer. ». aromatics
«alkanes
4. carboxylic acids
Timecoffight (TOF) mass analyzers
Choose one 2. Allow simultaneous detection of all species and have unlimited mass ranges
species
«. Require extremely high vacuum conditions to avoid colisions of fons and are often paired with
pulsed ionization sources
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, Measure the time requied for an ion to travel a known dlstance, dependent on the mass of the
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4d. All of the above
Ina mass spectrum of an alcohol, the molecular ion i usually small or non-existent due to
CChoase one 2. Cleavage of the hydroxy! group
answer. b Rearrangement of the molecule to form an ester
«Cleavage ofthe C-C bond adjacent tothe hydroxyl group
4, Formation ofa dimeric species
|W analysis ofa nicrogen-containing molecule shows a molecular ion peak with an adé miz ratio.
CChoase one 2. It contains an even number af nitrogen atoms
answer. b, It contains an odd numberof nitrogen atoms
«Teas rearranged via the MeLafferty rearrangement
4. The mass analyzer needs to be recalbrated; nitrogen containing molecules always give an even
m/z ratio
Which of te following i true about sector mss analyzers?
Choose one 2. They are inexpensive and compact
answer. b, They have low resolution and senstivty
«They are Incompatiole with EST and MALDI ionization methods
4. They can detect only low mass ranges
(Quadrupole and fon trap mass analyzers isolate ions for analysis by
Choose one 2. Varying the applied voltage and radiofrequency potentials
answer. », Accelerating lons through an electric felé
«. Aceleratng ions through a magnetic fla
4, Desorption from an electrode surface
‘Why i inductively coupled plasma (ICP) typically only used as an ionization method for elemental analysis?
Choose one 2. Only low molecular weight molecules can be analyzed.
answer. b, It requires the sample to be clssolved in a carrier gas prior to sample injection.
alkenes > alkanes
answer. b Alkanes > alkynes > alkenes
6 Alkenes > alkynes > alkanes
4d. Alkynes > alkanes > alkenes
In nor-tinear molecules, how many fundamental vibrations may exist (letn = the number of stom)?
Choose one 230-6
answer. bones
cn
2m
‘Why are some fundamental vibrations not observed?
Choose one 2. They exist outside ofthe mid-IR (observed) region,
answer, b, They are too weak or ovetap with other visations,
They are degenerate with other vibrational mades.
4. All of the above are correct.
In order for an IR vibration o be allowed, what condition must be met?
CChoose one ‘2. There must be a change in dipole moment ofthe molecule,
answer, b, There must be a change in the polarizability of the molecule
«The spin state ofthe molecule must fp.
4. There must be @ chromopharie species,
‘Which of the following statements about IR spectroscopy is FALSE?
Choose one 2, Absorptions due to C=0 bond stretching are generally weak
answer, b, Stretching frequencies are higher than corresponding bending frequencies,
«Single bonds have lower stretching frequencies than triple bonds.
4. Conjugation lowers the energy required to cause a bond to stretch.
The stretching frequency of which funeslonal group would be most useful in the detection of metal ligand complexes?
Choose one 20H
answer, bco
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coca
ocH
The shife in the C=O stretching frequency in a metaligand complex i influenced by all ofthe following except
CChoase one 12. The electron density of the metal center,
answer. b, The geometry ofthe molecule,
«The electron-donating or electron-nithdrawing effects of other ligands.
4d. The intensity ofthe infrared source used.
Pump-probe experiments in infrared spectroscopy can result in information about
Choose one 2 The molecular functional group vibrational fetes.
answer. b, The mechanisms of radiaactve decay.
«The amount of p-backbonting cheracter in a metaligand bond,
4d. The electronic transition levels within a molecule.
The vibrational ifetime of molecular functional groupe is dificult to study directly because
Choose one ‘2, They occur on the picoseconds timescale.
answer, », The funcional groups undergo rapid isomerizations.
«The electron donating abllties interfere with detection.
4. The intense olor of the molecules does not allow transmission of the source radlation.
The fingerprint region of the IR spectra correspond to
CChoose one 2. Bending frequencies
answer, b, Stretching frequencies
«Symmetric made frequencies
4. Asymmetric mode frequencies
How many fundamental vibrations would exist for ethyne (HCCH)?
Choose one a7
answer. bs
<8
a
‘Within the 3500-3300 en region, how can primary, secondary, and tertary amines be distinguished?
Choose one 2. Primary amines have two bands, secondary amines have one ban¢, and tertiary amines have
answer. no NH stretch,
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». Primary amines have one band, secondary amines have two bands, and tertiary amines have
three bands
«Primary amines have no bands, secondary amines have one banc, and tertiary amines have
‘wo bands,
4, Primary and tertiary amines have intense single bands, while secondary amines have two weak
bands
Hydrogen bonding causes the hydroxyl IR band to do what?
Choose one 2. Shift to lower frequencies and broaden
answer: », Shift to higher frequencies and sharpen
«Shift to higher frequencies and broaden
4, Shift to lower frequencies and sharpen
Which ofthe following regions would be most useful in determining the substcution patterns ofan alkene?
Choose one 2. The =CH stretch, occuring between 3100 - 3010 wavenumbers
answer. b. The =C+H out-ofplane bend, occurring between 1000 - 650 wavenumbers
«The C=C stretch, curring at 1660 - 1600 wavenumbers
4, None ofthe above would indicate substitution pattems,
The aromatic overcanelcombination bands (occurring between 2000 and 1667 em!) can be useful in determining
CChoase one 2. The rng substitution pattern (ortho, meta, para, ett)
answer: b, The number of carbons present in the aromatic ring
«The rate of proton exchange between the solvent and the analyte
4d, The cegree of resonance within the aromatic ng
Ethers, esters, and alcohols all contain C-O stretching bande. How can an ether be distinguished from the other wo
compounds?
Cchoase one The absence of
answer. b, Alcohols and esters have spt C-0 bands, while ethers show only one bend.
«The CO band of an ether appears ina ifferent region than that af an alcohol or ester
4d, Alcohols and esters have very broad C-O bands due to hydrogen bonding, while ethers have &
very sharp band.
‘and 0-H bands eliminate esters and alcohols.
Identify tis compound
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1004
8
i
i
&
1
Relative Intensity
&
L
20+
20 40 60 80 100 120 140 160 180 200 220
m/z
Choose one 2.2,4,6-trinivotoluene
answer. », 3-aminatoluene
2aminestyrene
4. pritrotoluene
7
Identify this compound
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woe
Cchoose one 2. methanol
answer, b. methane
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« formaldehyde
4d. acetone
72
Identify this compound
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Be.
i
CChoase one 2, ethylsothiocyanate
answer. ». isoamyl alcohol
«propylene glycol
4d. ethypropylether
73
Identify this compound
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sisnots
‘ ,
Bs De
A i ie
4 i
K (
a 7 gay a =
choose one 2. ghenphosphine
ansver b. doo eer
«. benzyl bromide
4 heraturoberzene
ry
Identify this compound
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1004
204
&
L
Relative Intensity
&
L
20+
| anced | Ihe dreclthetieredl mM
o T T 1 T T T Tey T T ry
2 406080 100 120 «14 469 tg0 200. 230
m/z
CChoase one 2. dbromochlorefluorometane
answer. ». carbon tetrachioride
«, bromochlorofluroiadomethane
«methylene bromide
75
The electromagnetic radiation used for NMR spectroscopy fills in which region?
CChoase one 2. Microwave
answer. boxy
Gemma ray
4, Radio wave
76
Cand '60 nuclei cannot be observed by NMR spectroscopy. Why!
Choose one 2. They have zero spin and yield no signal
answer. b, They have ow natural abundance.
«. They interact too strongly withthe magnetic fel
4. They cause complex spin-spin interactions, which cannot be interpreted.
7
All of the following are |= 4 systems, except
CChoose one a
answer. bie
oMNn
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dH
[Nuclei with even masses and odd numbers of protons and nevtrans
Cchoase one 2. Have integral spins and can be observed by NMR.
answer. b, Have fractional spins and can be observed by NMR.
«Have integral spins and cannot be observed by NMR.
4d. Have fractional spins and cannot be observed by NMR.
Which ofthe following is NOT a reason why tetramethylsline (TMS) is often used for a reference in NMR spectroscopy?
Cchoase one 2: Itis chemically inert and miscible with organic solvents.
answer. b. It gives a single, snarp peak in 2 region where other organic molecules do nat have signals
«Its signal appears atthe same frequency regardless of the applied magnetic fed.
4. Itis easily removed from the sample after analysis.
Which ofthe following would be a poor choice a a proton NMR solvent?
CChoase one 2. Restone-d6
answer b, Deuterium oxide
«Carbon tetrachloride
4d. otoluene
‘What structural information does 'H-NMR spectroscopy NOT provide
Choose one 2. The numberof diferent types of hydrogens in a molecule,
answer, », The relative numbers of cfferent types of hydrogens,
«. The electronic environment of differen types of hydrogens:
4. The relative abundance of afferent isotopes of hydrogen.
The universal sale for reporting chemical shifts in NMR is
Choose one ae
answer. ppm
Mie
denn
‘An NMR spectrum is acquired by
Choose one 2. Varying the magnetic field with @ constant rf signal
answer. ». Varying the rf signal with @ constant external magnetic fe.
Varying the signal and the external magnetic fel, simultaneously
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4
‘a and bare correct.
84
Which of the following appears the most lowfield?
Choose one 2. Aldehydes
answer. », Alcohols
Alkanes
<. Aromaties|
85
Iva proton fs more "shielded" ie will appear
CChoase one 2. Lowfied, at 8 low ppm or Hz
answer, b. Highfield, at alow ppm or Hz
Lowfield, ata high ppm or He
4. Highfield, at @ high ppm or He
86
Which of the following correctly describes the relative intensities of splitng an NMR peak?
Choose one 2. Thiplet-1:3:1
answer, , Quartet - 1:4:4:1
«.Pentet = 1:3:5:3:1
4, Sextet ~ 1:5:10:10:5:1
87
‘Adjacent protons can act as magnets and affect the amount of radiation required for proton resonance in NMR. This
Choose one 2. Rapid relaxation and unreliable integration results
answer, b. Spin-spin coupling, resulting in peak spiting
Increased shielding, forcing the chemical shift to be lower
4. Decreased shielding, forcing the chemical shift to be higher
88
By irradiating two dissimilar nucle, an increase in the difference in population between the “spin-aligned” and "spin-opposed”
states occurs and increases the signal inensiy. This is referred to as
Choose one ‘2 Nuclear Overhauser Enhancement (NOE)
answer, b, Heteronudear Correlation Spectroscopy (HETCOR)
«Correlation Spectroscopy (COSY)
4d. Distortionless Enhancement by Polarization Transfer (DEPT)
89
Discortionless Enhancement by Polarization Transfer (DEPT) would allow which of the following NMR peaks to be
Aistinguished from ene another?
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Choose one ‘2 Methylene groups from methyl groups
answer. b. Hydroxyl groups from amine groups
«Othe, meta, and para substituent groups an a benzene tng
4. Aromatic carbons from aliphatic carbons
90
Ina COSY spectrum, the datk spots along the diagonal
Choose one 2. Do not yield structural information because they correspond to the same peak on each
answer. coordinate axis.
b. Allow distinctions to be made between heteronuclear coupling constants
«. Do not give any structural identifiation because they are too intense to be deconvoluted.
4d. Give the most structural information because they diferentate between diferent
hybrizations
a1
‘Aralysis of two peaks in a proton NMR spectrum gives a 3:2 integration. This means that
Choose one '. There are three hydrogens on one carbon end two on another.
answer, b. The ratio between the two types of hydrogen environments is 3:2.
«One of the peaks is @ methyl group and the other isa methylene group.
4. The peaks belong to a straight cha aliphatic compound
92
Magnetic Resonance Imaging (MRI) isan application of NMR spectroscopy in which ofthe following ways?
Choose one 2 Tt measures the distrbution of hydrogen nuclt in the boy.
answer, b. It measures the distribution of carbon nucle in the body.
«Tt seans fer unique nuclei within human tissues.
4. Itallows a non-invasive measure of bone dent.
93
Identify this compound
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200
T T T T T T T T
180 160 140 120 100 80 60 40
pen
2. 2-butanone
», butanol
butane
. 2utene
94
Identify thie compound
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100-4
804
8
L
20+
Relative Intensity
8
1
a
8
150 175
2. 2,2-dichloropropane
. 2,2-dibromopropane
. 2,2-dichloropropanol
4d, 2,2-libromopropanol
Identify this compound
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eo we
T T T 1 T T r J i '
10 3 8 7 6 & 4 3 2 af oO
weneo-222 BR
choose one a. actatenyce
Dnsver b. acetic ai
ethane
4. det eter
Identify this compound
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answer. b. ethanethiolate
4. samy oete
97
Identify this compound
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1008 8 u 6 5 4 3 2 1 °
wen-02-218 ppm
Choose one 2. ethylvinyl ether
answer. ». Isopropyl ether
«. Pbutylacetate
. butyric acid
98
Identify this compound
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100]
20+
>
2
5 60-4
g ie fen .
3B 404
3
g
20
Meech Ll ik
° ' pete ert cerry ' potty
2 OO Oe
m/z
choose one 2. methylene corde
answer. b. 1,1-dicholoroethane:
«carbon tetrachloride
4d. dlbromomethane
99
Identify this compound
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Choose one 2, Putyleyclohexane
answer b, ebutybenzene
«. ebutythexanol
4d. tbutylyclohexanone
100
Identify thie compound.
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Choose one 2. triethylamine
answer ». tributyiamine
«.dinitroethane
4. ammonium acetate
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