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Multiple Choice Questions: Each question is worth 2 points.

There is no penalty for wrong


answers. (10 points)

1) Select the INCORRECT statement about NMR spectroscopy.


a. The stronger the magnetic field in an NMR instrument, the larger the energy
difference between the alpha and beta spin states of a nucleus.
b. Radiowaves with energy equal to the resonance frequency of a nucleus cause a
transition from the parallel to antiparallel spin state.
c. The signal detected by the NMR instrument is the result of having an equal
number of nuclei in the alpha and beta spin states.
d. The resonance frequency of a given nucleus in influenced by nearby electrons, but
not nearby nuclei.

2) How many positive signals would be expected in a DEPT-135 spectrum of the molecule
shown below?
a. 2
b. 3
c. 5
d. 6
e. 8

3) Which of the following molecules would be expected to generate the largest M+2 peak in
its mass spectrum?
a. Chlorobenzene
b. Bromobenzene
c. Toluene
d. Nitrobenzene

4) Select the INCORRECT statement about Mass Spectrometry?


a. The base peak is the peak with largest intensity.
b. The molecular ion peak is the peak with the largest m/z ratio.
c. The molecular ion peak represents molecules composed of the most abundant
isotopes of each element.
d. Peaks with a m/z ratio below that of the molecular ion represent positively
charged fragments formed through bond cleavages.

5) Select the INCORRECT statement about IR spectroscopy.


a. The more atoms a molecule has, the more vibrational modes it has.
b. Vibrational modes are IR active if they change the dipole moment of the molecule.
c. Carbonyl stretches are more strongly absorbing than alkene stretches because the
C=O bond is a stronger bond.
d. Conjugated double bonds absorb at a lower frequency because of the partial single
bond character that conjugation introduces.
Short answer questions: Provide your answers in the spaces provided.

1) For each of the following structures, circle the most deshielded hydrogen(s) and put a star
next to the most shielded hydrogen(s). (4 points)

2) How many signals would you expect to see in the 1H and 13C NMR spectra of the following
compounds? For the hydrogen signals, indicate their relative integrations expressed as the
lowest possible whole number ratio. (9 points)

# of H signals
Relative integration
of H signals
# of C signals

3) For each of the following pairs of compounds, circle the technique which would most easily
distinguish between the structures. (4 points)
6) Propose a structure for X (C6H10O) given the following data. For full marks, you must show
your work, including the assignment of ALL peaks in the 1H and 13C NMR. Note that there are
two possible structures for X; either one will be accepted. (10 points)

IR spectrum Low-resolution MS

1
H NMR spectrum

13
C NMR spectrum

Proposed structure of compound X:


7) Fill in the missing reagents and/or products (major only) for each of the following synthetic steps.
More than one step may be required for some transformations. (30 points; 2 points per box).
8) Provide a detailed stepwise mechanism for each of the following reactions. Unless otherwise
indicated, resonance contributors are not required.

a) (3 points)
b)
(5 points)
c)

(6 points)

(Include all significant resonance contributors for any charged intermediates; clearly
indicate which resonance contributor is the most stable.)
9) Design a synthesis for ONE of the following compounds starting from aniline (circle the one
you choose). Show the reagents and reaction conditions required for all steps, as well as the
structure of any intermediates formed. NOTE: You do NOT need to show any retrosynthetic
planning OR any mechanisms for this question. (8 points)