Quiz #1

Name __________________________________
25 points total SHOW YOUR WORK
1. Short answer question.
(a) Absorption ________________ is the measurement of the amount of light absorbed by a
compound as a function of the wavelength of light.
(b) The energy of a photon is ________ proportional to its wavelength.

(c) The energy of a photon is ________ proportional to its frequency.

(d) An infrared wavelength of 4.48m is equivalent to a wavenumber of ________ cm-1.

(e) What wavelength in mm is equivalent to a wavenumber of 1750 cm-1?

(f) The region of the IR spectrum which contains the most complex vibrations (600-1400 cm-1) is
called the _____________ region of the spectrum.

(g) In order for a vibration mode to be observable in the IR, the vibration must change the ________
of the molecule.

(h) An ___________ molecular ion peak usually indicates the presence of an odd number of nitrogen
atoms in the molecule.

(i) The mass spectrum of alcohols often fail to exhibit detectable M peaks but instead show relatively
large ________ peaks.

(j) In a mass spectrum, the peak of greatest abundance is referred to as the ________.
(k) In the presence of an external magnetic field the approximate ratio of 1H nuclei with spins
compared to spins is respectively: ________.
(l) ________ is commonly used as an internal reference in NMR spectroscopy; its signal is assigned d
= 0 in 1H and 13C NMR spectroscopy.
(m) On a 90 MHz spectrometer, calculate the frequency at which a proton absorbs if it appears at 4.20
ppm.
(n) What is the relative area of each peak in a quartet spin-spin splitting pattern?
(o) Give two reasons why 13C NMR is less sensitive than 1H NMR.
(p) Why is carbon-carbon splitting typically not seen in 13C NMR spectra?

2. Rank the following bonds in order of increasing stretching frequency (cm-1) in IR spectroscopy:

3. Rank the following bonds in order of increasing stretching frequency (cm-1) in IR spectroscopy:

4. If the mass spectrum of chlorobenzene shows a peak with an m/z value of 114, having an abundance
of 15%, calculate the m/z value and approximate abundance of the molecular ion peak.

5. For the following compounds, give approximate frequencies for distinctive peaks in the IR spectrum.
(a)

(b)

(c)

6. The following is the mass spectrum of an unknown liquid with bp 100-105 C.

(a) What compound is this?
(b) Suggest structures for the fragments at 136, 107, and 93.
(c) Why is the peat at m/z 57 so strong?

7. For the following compound shown below,

(a) Sketch 1H spectrum, showing approximate chemical shifts
(b) Sketch 13C spectrum (totally decoupled, with a singlet for each type of carbon), showing
approximate chemical shifts
(c) Sketch 13C spectrum in the off-resonance-decoupled spectrum
(d) Sketch 13C spectra expected using the DEPT-90 and DEPT-135 techniques.

8. Predict the multiplicity and the chemical shift for each shaded proton in the following compounds.

9. Deduce the identity of the following compounds from the spectral data given.
(a) C5H10O:
1
H NMR (ppm): 1.2 (6H, doublet), 2.1 (3H, singlet), 2.8 (1H, septet)
-1
IR (cm ): 2980, 1710
MS: m/z 71, 43

(b) C9H7Cl
-1
IR (cm ): 3050, 2950, 2220, 1620
1
H NMR (d): 7.8 (2H, d), 7.2 (2H, d), 2.1 (3H, s)
13
C NMR (d): 140 (s), 132, (s), 125 (d), 122 (d), 88 (s), 83 (s), 18 (q)
(c) C3H6Br2:
1
H NMR (d): 2.4 (2H, quintet), 3.5 (4H, triplet) (ppm)