NAME: ______________________________

CHM 2210 - Dr. Iannotti

Assignment 2 CH 15 and 16: IR, Mass Spectrometry and NMR
40 points (2 points each)
1.

Which of the following processes takes place upon absorption of infrared radiation?
a. bond vibration
b. electron excitation
c. nuclear spin flip
d. electron spin flip

2. What is required for a bond to give an infrared absorption?

a. a change in bond length during vibration
b. a change in bond angle during vibration
c. a change in bond dipole during vibration
d. a change in reduced mass during vibration

3. Which of the following bonds undergoes stretching at the highest frequency?

a.
b.
c.
d.

OH
CH
C=O
CC

4. Which of the following bonds (circled) gives the weakest absorbance in the infrared
spectrum?

5. Which of the following functional groups is likely to be present in a molecule that has peaks
in the infrared spectrum at 1630-1820 cm-1 (strong, broad) and 1000-1250 cm-1; but does
not have peaks at 3200-3650 cm-1?
a. alcohol
b. aldehyde or ketone
c. ether
d. ester
6. Which of the following compounds gives an infrared spectrum with peaks at 3000-3500 cm
and ~1750 cm ?

7. How could you distingish between 1-hexyne and 2-hexyne by infrared spectroscopy?

ANS:

8. Which of the following is the definition of the base peak of a mass spectrum?
a. the peak corresponding to the most abundant ion
b. the peak corresponding to the ion with lowest m/e
c. the peak corresponding to the molecular ion peak
d. the peak corresponding to the ion arising to loss of a proton from the molecular
ion
9. Which of the following corresponds to the molecular ion in EI mass spectrometry?
a. the most abundant ion
b. the ion with the smallest m/e
c. the ion formed by removal of an electron from the molecule
d. any ion formed by fragmentation of the molecule
10. Which of the following sets of molecular ions does an alkyl bromide possess?
a. two molecular ions in a 2:1 ratio separated by two mass units
b. two molecular ions in a 1:1 ratio separated by two mass units
c. three molecular ions in a 1:2:1 ratio separated by two mass units
d. two molecular ions in a 3:1 ratio separated by two mass units
11. Which of the following is most consistent with a molecule having a molecular ion with m/e of
77?
a. the molecule contains bromine
b. the molecule contains nitrogen
c. the molecule is an alcohol
d. the molecule is a hydrocarbon
12. What are the most common products of the fragmentation of a molecular ion?
a. two radicals
b. an anion and a cation
c. a radical and a cation
d. two cations
13. Which of the following bonds of the octane radical cation is least subject to fragmentation?

14. Which of the following gives rise to a prominent M - 18 peak in the mass spectrum?
a. hexane
b. 1-chloropentane
c. 1-pentanol
d. 3-methylpentane
15. Which feature in the 1H NMR spectrum provides information about the number of types of
different protons in a compound?
a. number of signals
b. integral
c. splitting
d. chemical shift
16. Which feature in the 1H NMR spectrum provides information about the electronic
environment of the protons in a compound?
a. number of signals
b. integral
c. splitting
d. chemical shift
17. Which of the following is not true regarding 1H NMR spectroscopy?
a. "shielding" leads to peaks at lower values of
b. a "downfield" peak appears at a higher value of
c. for a particular proton depends on the magnetic field strength of the instrument
used.
d. on a 300 MHz instrument, a proton that adsorbs irradiation at a frequency 1200
Hz higher than the adsorption of TMS appears at 4 ppm.
18. How many sets of equivalent protons are there in hexane?
a. 2
b. 3
c. 6
d. 7
19. What is the splitting of the signal in the 1H NMR spectrum for the methyl protons of
propane?
a. singlet
b. doublet
c. triplet
d. quartet
20. Which of the following combinations of peaks appears in the 1H NMR spectrum of butane?
a. a triplet and a doublet
b. a triplet and a quartet
c. a triplet and a sextet
d. two singlets