Sultan Qaboos University

Department of Chemistry

CHEM4426 Spectroscopic Structure Determination Sat, 13thJune, 2020

3:00 –7:00 pm
Final Exam

Name: ……………………………..
Spring 2020
ID No: …………………………….

Total Marks: 80

Question Total Marks Marks Obtained

Question 1 5

Question 2 16

Question 3 7

Question 4 12

Question 5 7

Question 6 16

Question 7 7

Question 8 10

TOTAL 80

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Q-1. Select the correct answer of the following questions: (5 Marks)

I. The 1H-NMR signal splitting of C-5 hydrogens in the following molecule in chiral solvent is:

a) septet b) doublet c) doublet of doublets d) triplet

II. The C=O stretching IR band in the following molecule is:

a) 1240 cm-1 b) 1640 cm-1 c) 1810 cm-1 d) 1715 cm-1

III. The MS McLafferty rearrangement peak in the following molecule is:

a) 44 b) 60 c) 58 d) 99

IV. The number of 13C-NMR signals in the following molecule is:

a) 4 signals b) 5 signals c) 6 signals d) 3 signals

V. The number of 1H-NMR signals in this molecule is:

a) 3 b) 4 c) 5 d) 6
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Q-2. Study the following MS spectrum of 3-methyl-2-pentanone and answer the subsequent questions:
(16 Marks)

I) In the spectrum, label the base peak and the molecular ion peak.
II) Draw a structure for the base peak fragment, and explain what makes it a base peak fragment?

III) Draw the mechanism and give the name of the fragmentation that leads to the formation of the base peak
fragment.

IV) Draw the mechanism and give the name of the fragmentation that leads to the formation of fragment with
mass 72.

V) What is the structure of fragment 85? Why this fragment is not the base peak?

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Q-3. The EI mass spectrum of an unknown compound is given below. Interpret the spectrum and identify the
structure of the compound from the characteristic fragments. (7 Marks)

Q-4. I. Match the following IR absorption bands with the given molecules. (4 marks)

II. Explain the observations in the IR of the following stereoisomers. (4 Marks)

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III. A student recorded IR spectrum (neat) of an unknown compound. He suspected that the IR spectrum
belongs to one of these 3 compounds. Circle the correct compound. Explain (4 Marks)

Explain:

5
Q-5. Analyze the following IR spectrum; calculate DU, identify the characteristic IR bands and give one
possible structure for the compound with molecular formula (C5H10O2). (7 Marks)

Q-6. I. Explain why the circled carbon in compound-1 shows 13C-NMR downfield signal at 130.1 ppm
while the circled carbon in comound-2 shows an upfield signal at 115.2 ppm? (4 marks)

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II. Study this molecule and answer the following questions: (12 Marks)

a) How many different 1H-NMR signals you will expect for the molecule.
b) Circle the most deshielded hydrogen(s) in the molecule.
c) Which carbon atom is most shielded?
d) Are the two hydrogens of carbon-2 homotopic, enantiotopic or diastereotopic? Explain

e) Put in the following

Hydrogen number table chemical
the estimated
shiftchemical
(ppm) shifts of all hydrogens and(Splitting)
Multiplicity their splitting (solvent: CDCl

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Q-7. Analyze the following 1H-NMR spectrum; calculate DU, assign all the 1H-signals and give the
structure of the compound. (C6H10O3) (7 marks)

Q-8. Provide a structure consistent with the set of spectra provided. (10 marks)
- Interpret the key MS fragments and IR bands.
- Assign all the NMR chemical shifts
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- Analyse the H-H cosy and H-13C cosy spectra

9
Q-9. Write your analysis and answer for question-9 in this page:

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End of the Exam

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