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Experiment 38 Determination of the Structure of a Natural Product in Anise Oil
(b) The pH of the reaction mixture was 7 when you filtered it, and you
obtained a brown solid. (c) You recorded the IR spectrum of the oxida-
tion product rather than that of anisene itself.
6. Describe the probable role of the phase-transfer catalyst in this reac-
tion, giving equations for the relevant reactions.
7. Following the format in Appendix V, construct a flow diagram for the
synthesis of your methoxybenzoic acid.
8. (a) Draw the structure of the compound C10H200 that is obtained by
the catalytic hydrogenation of anisene. (b) Draw the structure of the
compound C,H,OH that is obtained when anisene is treated with
9. You could confirm the structure of anisene by synthesizing it from
known starting materials. Outline a synthesis of anisene from benzene
and alcohols that have four carbon atoms or fewer.
10. The structure shown has been proposed for coniferyl alcohol, which
can be obtained the hydrolysis of coniferin, a natural product found
in the sap of conifer trees. Assuming that the structure of coniferyl
alcohol had not been reported in the literature, describe how you
would go about proving its structure. Indicate what chemical tests and
degradations might be carried out, and describe the expected results
and conclusions. Summarize the information that could be derived
from infrared analysis. Then show how the alcohol could be synthesized
from readily available starting materials.
proposed structure for
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1. Derive a systematic name for anisene and find its common name in The
Merck Index or another reference book.
2. (a) Write a balanced equation for the reaction of anisene with potassi-
um permanganate, assuming that the products include manganese diox-
ide and the potassium salt of acetic acid. (Note: The reaction mixture is
alkaline.) (b) Assuming that 5 drops of anisene is about 1.0 mmol, cal-
culate the mass of potassium permanganate required to oxidize that
much anisene and the percentage in excess that was actually used.
3. (a) The three carbon atoms of anisene’s side chain might have formed
two separate side chains rather than one. Give the structures of these
side chains. (b) Give the structures of all the dicarboxylic acids that
could have resulted from complete side-chain oxidation of anisene had
it contained these two side chains.
4. (a) Using a balanced equation for the oxidation reaction (see Exer-
cise 2a), calculate the atom economy and reaction efficiency of your
synthesis. (b) Describe some green features of your synthesis, and any
that aren’t so green.
5. Describe and explain the possible effect on your results of the following
experimental errors or variations. (a) You forgot to add the Aliquat 336.
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