CHEMISTRY DEPARTMENT

Name of Student: ___________________________________________ ID Number ____________

SPECTROSCOPY AND STRUCTURE ELUCIDATION

(Term 3, AY 2022-2023)
I.
1. 6. 11. 16.

2. 7. 12. 17.

3. 8. 13. 18.

4. 9. 14. 19.

5. 10. 15. 20.

II.

1.

2.

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CHEMISTRY DEPARTMENT

SPECTROSCOPY AND STRUCTURE ELUCIDATION

DIRECTIONS:
1. The exam consists of 15 items of multiple choice-type of questions. Choose the letter that
corresponds to your choice of the best answer. Print your answer and use capital letters
only. There is only one answer per number. Each number is worth 2 points.
2. During the conduct of the examination, students are not allowed to
a. borrow calculator, pen, eraser or correction fluid
b. use pencil on the answer sheet.
c. Use the cell phone as calculator and/or attend to calls or messages sent through the
cellular phone. For this reason, kindly switch off your cellular phone(s).
d. refer to personal copies of the Periodic Table or notes
e. talk to one’s seatmate
f. leave the examination room without prior permission from the proctor.
g. be involved in any form of cheating
3. Please submit the questionnaire, answer sheet and test booklet at the end of the examination
period to the proctor.
God Bless You and Good Luck!
__________________________________________________________________________________
The exam starts here.

I. Multiple Choice (40 points)

1. Which of the following statements is wrong? 5. Which H of 1-chloropent-2-ene shows the largest
chemical (downfield) shift in its NMR spectrum?
A. UV absorption is attributable to electronic
transitions. A. the H on C1
B. UV spectra provide information about B. the H on either C2 or C3
valence electrons. C. the H on C4
C. IR absorption is attributable to transitions D. the H on C5
between rotational energy levels of whole
molecules. 6. Which C of hex-3-en-2-one shows the largest
D. NMR spectrometers use radiofrequency (most downfield) chemical shift in the NMR
electromagnetic radiation. spectrum?

2. Which is the correct order of increasing wave A. C1 C. C3

number of the stretching vibrations of (1) C-H B. C2 D. C4
(alkane), (2) O-H (alcohol), (3) C=O (ketone),
and (4) C≡C (alkyne)? 7. Which of the following statements regarding IR
spectroscopy is wrong?
A. (4) < (3) < (2) < (1)
B. (3) < (4) < (2) < (1) A. IR radiation is higher in energy than UV.
C. (3) < (4) < (1) < (2) B. IR spectra record the transmission of IR
D. (4) < (3) < (1) < (2) radiation.
C. Molecular vibrations are due to periodic
3. How many signals does the aldehyde motions of atoms in molecules, and include
(CH3)3CCH2CHO have in 1H NMR and 13C NMR bond stretching, torsional changes, and bond
spectra? angle changes.
D. IR spectra give information about bonding
A. five 1H signals and six 13C signals features and functional groups in molecules.
B. three 1H signals and four 13C signals
C. five 1H signals and four 13C signals 8. Which of the following statements regarding
D. three 1H signals and six 13C signals NMR spectroscopy is wrong?

4. Which of hydrogens in the molecule gives a A. NMR signals towards the left of the spectral
triplet signal in a normal 1H NMR spectrum? chart correspond to larger chemical shifts.
B. Chemical shifts are larger when the
frequencies of the radiation which induces
the nuclear transitions are higher.
C. Chemical shifts are larger when shielding
effects are greater.
A. hydrogen a C. hydrogen c D. A hydrogen signal splits into n+1 peaks by
B. hydrogen b D. hydrogen d spin-spin coupling when the number of
equivalent hydrogen atoms on adjacent
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atom(s) is n, and no other neighboring atoms 14. How many signals does the unsaturated ketone
are involved. (CH3)2CHCH2C(O)CH=CH2 have in 1H NMR
and 13C NMR spectra?
9. Which of the following statements regarding
mass spectrometry is wrong? A. five 1H signals and six 13C signals
B. six 1H signals and six 13C signals
A. In a normal mass spectrometer, electron C. six 1H signals and seven 13C signals
impact causes a molecule to lose an electron D. five 1H signals and seven 13C signals
and become a molecular radical cation which
decomposes into fragment cations and 15. Which of the following statements in the context
radicals. of 1H NMR spectroscopy is true?
B. Only cations can be detected by a normal
mass spectrometer. A. Arene C-H chemical shift (δ) values are
C. A compound whose molecules contain just greater than simple alkenes C-H chemical
one bromine atom shows two molecular ion shift values because of the aromatic ring
peaks of similar intensity, one at +1 and one current.
at -1 of the average m/z value. B. Arene C-H chemical shift (δ) values are
D. Molecular ion peaks always have even- smaller than simple alkenes C-H chemical
numbered values of m/z. shift values because of the aromatic ring
current.
10. Which of the following statements is wrong? C. Arene C-H signals are always multiplets.
D. Arene C-H signals are always singlets.
A. A conventional mass spectrometer employs
high energy UV radiation. 16. Which carbon of hex-3-en-2-one has the
B. A conventional mass spectrometer does not smallest (most upfield) chemical shift in the
employ a spectrophotometric detector. NMR spectrum?
C. Conventional mass spectrometry does not A. C1 C. C3
always require samples of high purity. B. C2 D. C4
D. A mass spectrum does not show signals due
to uncharged radicals. 17. Which indicates the multiplicities for hydrogens
on C1, C3, and C4 of butanone attributable to
11. Absorption of radiation in the UV range spin-spin coupling in its 1H NMR spectrum?
attributable to n→π* electronic transitions is
characteristic of which of the following types of A. Hs on C1, singlet; Hs on C3, doublet; Hs on
compounds? C4, triplet.
B. Hs on C1, singlet; Hs on C3, triplet; Hs on
A. Aromatic hydrocarbons. C4, quartet.
B. Unsaturated carbonyl compounds. C. Hs on C1, singlet; Hs on C3, quartet; Hs on
C. Non-conjugated polyenes. C4, triplet.
D. Conjugated polyenes. D. Hs on C1, triplet; Hs on C3, doublet; Hs on
C4, triplet.
12. Which of the following statements is wrong?
18. Which indicates the correct order of carbon
A. he wavenumber of a band in an IR spectrum chemical shifts of the four carbons of the
is proportional to the frequency of the following compound.
associated molecular vibration.
B. Water is a good solvent for recording UV
spectra of water-soluble compounds.
C. Water is a good solvent for recording IR
spectra of water-soluble compounds.
D. Hydrogen bonding in hydroxy compounds A. CMe < C2 < C3 < C1
leads to broadening of spectral bands B. CMe < C3 < C2 < C1
attributable to O-H stretching vibrations. C. CMe < C2 < C1 < C3
D. CMe < C1 < C2 < C3
13. Which is the correct order of increasing wave
number of the stretching vibrations of (1) C-H 19. Which of the following statements regarding
(alkane), (2) C-H (alkene), (3) C-H (alkyne), and electron-impact mass spectrometry is true?
(4) C-H (arene)?
A. Samples need isotopic labels.
A. (1) < (2) ≈ (3) < (4) B. The base peak is formed by loss of one
B. (4) < (3) ≈ (2) < (1) electron from each vaporized molecule by
C. (3) < (4) ≈ (2) < (1) an electron beam.
D. (1) < (4) ≈ (2) < (3) C. Compounds must have a functional group to
show a mass spectrum.

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D. A meaningful mass spectrum can

sometimes be obtained on a very small
sample of an impure compound.

20. Which of the following statements regarding

mass spectrometry is false?

A. The base peak of a simple ketone is usually

attributable to an acylium ion.
B. The molecular ion of carbonyl compounds
with a -C-H readily undergoes elimination of
an alkene to give a relatively stable enol
radical cation.
C. The molecular ion peak of some alcohols is
very weak because it readily loses an alkyl
radical to give a relatively stable oxonium
(hydroxycarbenium) ion.
D. Structurally isomeric alkanes cannot be
distinguished by low resolution mass
spectrometry.

END OF MULTIPLE CHOICE

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CHEMISTRY DEPARTMENT

II. STRUCTURAL ELUCIDATION (15 points each)

Directions: Determine the structure of the following compounds based on the different spectral
analysis performed. Justify your answer by explaining the results of every spectrum.

1.

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CHEMISTRY DEPARTMENT

2.

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