Chapter 12: Q59E (page 354)
Show how you might use a Wittig reaction to prepare the following alkenes. Identify the alkyl halide and the carbonyl components.
a.

b.

Short Answer
a.

b.

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Chapter 12: Q59E (page 354)
Show how you might use a Wittig reaction to prepare the following alkenes. Identify the alkyl halide and the carbonyl components.
a.

b.

a.

b.

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Question: At what approximate positions might the following compounds showIR absorptions?
(f)

Question: Camphor, a saturated monoketone from the Asian camphor tree, is used among other things as a moth repellent and as a constituent of embalming
fluid. If camphor has M+=152.1201 by high-resolution mass spectrometry,
what is its molecular formula? How many rings does camphor
have?
Question: How could you use infrared spectroscopy to distinguish between the
following pairs of isomers?
(a)
(b)
One consequence of the base-catalyzed isomerization of unsaturated ketones described in Problem 22-55 is that 2-substituted 2-cyclopentenones can be interconverted with 5-substituted 2-cyclopentenones. Propose a mechanism for this isomerization.

Assume that you are carrying out the dehydration of 1-methyl cyclohexanol to yield 1-methyl cyclohexene. How could you use infrared spectroscopy to determine when the reaction is complete?
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