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Name __________________________________
(f) The region of the IR spectrum which contains the most complex vibrations (600-1400
cm-1) is called the fingerprint ________ region of the spectrum.
(g) In order for a vibration mode to be observable in the IR, the vibration must change the
___dipole moment _____ of the molecule.
(h) An _____odd___ 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 __M-18______ peaks.
(j) In a mass spectrum, the peak of greatest abundance is referred to as the base peak ___.
(k) In the presence of an external magnetic field the approximate ratio of 1H nuclei with
spins compared to spins is respectively: __50:50______.
(l) __tetramethylsilane ______ 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. 378 Hz
(n) What is the relative area of each peak in a quartet spin-spin splitting pattern?
1:3:3:1
(o) Give two reason why 13C NMR is less sensitive than 1H NMR.
Natural isotopic abundance of 13C is about 100 times less than that of 1H or gyromagnetic
ratio of 13C is much smaller.
(p) Why is carbon-carbon splitting typically not seen in 13C NMR spectra?
Only 1% of the carbon atoms are 13C so the probability of two 13C nuclei being adjacent is
very small.
(b)
(c)
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
(CH3)2CHCOCH3
(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)