1. Determine the number of peaks you would expect to see from the following molecule
a. in a 1H NMR spectrum (do not count splitting patterns).
b. in a proton decoupled 13C NMR spectrum.
2. Determine the structure of this alcohol with the molecular formula C5H12O from its 1H NMR
300-MHz 1H NMR spectrum ppm (8)
The 13C spectrum of a compound with the molecular formula of C5H10O shows peaks at the
following locations. The type of carbon was revealed by DEPT spectra. Draw the structure of
one of the possible isomers.
8=17.6 (CH3), 25.4 (CH3), 58.8 (CH2), 125.7 (CH), 133.7 ppm (Cq)
4. Draw the structure of (Z)-3,7-dimethyl-3-octene
5. Decide which of the following statements are correct for compound A, compound B, both, or
neither of them (write "A", "B", "both", or "neither" on the line given):
a. This compound is more stable.
b. This compound is slightly polar.
C. This compound would release more energy upon hydrogenation.
6. 3-Hexanol is oxidized to the ketone. Where would you expect to see major changes in the IR
spectrum over the course of the reaction? Give approximate wavenumbers and peak shapes
of one appearing and one disappearing peak.
7. Determine the structure of the alkane producing the following mass spectrum. Draw the
fragments causing m/z = 43 and m/z = 85 (include charges and unpaired electrons) and
explain the intensities of these peaks in the mass spectrum.
8. a. Draw the major organic product of this E2 reaction.
b. Draw the conformer out of which this E2 reaction will occur in Newman projection.
C. What would the product look like if we would let this haloalkane react with KOtBu instead
9. Draw the mechanism of the following reaction leading to the major organic product.
Propose reagents to perform the following
11. a. Show the mechanism for the conversion of A into B (and its enantiomer).
b. How could A be converted into C? Show the mechanism.
12. Indicate how this reaction could be performed with good yield. Show the product of the first
step. Only one enantiomer of the product is shown. Show the enantiomer of the first step that
leads to this enantiomer in the product.
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