Problem
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1.
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Draw
a structure corresponding to the following IUPAC name:
3-methyl-2-buten-1-ol
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2.
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Give
an acceptable name for the following substance.
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3.
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Explain why nonafluoro-2-methyl-2-propoxide is a much weaker base than
tert-butoxide.
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Phenols
Refer to the data below to answer the following
questions.
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4.
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Refer
to Phenols. Which of the acids in the Table has the weakest conjugate base?
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Reaction 17-2
To answer the following questions, consider the
reaction below:
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5.
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Refer
to Reaction 17-2. On the structures provided below, draw arrows which account for the complete
stepwise mechanism for this reaction.
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Reaction 17-3
To answer the following questions, consider the
reaction below:
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6.
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Refer
to Reaction 17-3. Write the complete stepwise mechanism for the reaction. Show all intermediates and
all electron flow with arrows.
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Grignard Reagents
A highly useful
and general method for the synthesis of alcohols is the addition of Grignard reagents to carbonyl
compounds. Show what Grignard reagent and what carbonyl compound you would start with to prepare each
alcohol below. List all possibilities.
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7.
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Refer
to Grignard Reagents.
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Organic Products
Give the major
organic product(s) of the following reactions or sequences of reactions. Show all relevant
stereochemistry.
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8.
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Refer
to Organic Products.
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9.
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Outline the synthetic steps necessary to carry out the conversion below. You may use
any organic or inorganic reagents you need. Show the structures of all intermediate compounds that
would probably be isolated during the course of your synthesis, and show all necessary
reagents.
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10.
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Propose a structure for an alcohol that has the following 1H NMR
spectra.
C7H8O (neat solution; no
solvent)
Spectrum obtained from: SBDSWeb:
http://www.aist.go.jp/RIODB/SDBS
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