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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Aprobarbital, a barbiturate once used in treating insomnia, is synthesized in three steps from diethyl malonate. Show how you would synthesize the necessary dialkylated intermediate, and then propose a mechanism for the reaction of this intermediate with urea to give aprobarbital.

Question: Propose structures for compounds that meet the following descriptions:
(a)with IR absorptions at 3300 and 2150
(b)with a strong IR absorption at 3400
(c) with a strong IR absorption at 1715
(d) with IR absorptions at 1600 and 1500
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.

Two mass spectra are shown in Figure 12-8. One spectrum is that of 2-methyl-2-pentene; the other is of 2-hexene. Which is which? Explain.
a.

b.

How would you synthesize the following substances from benzaldehyde and any other reagents needed?
a.

b.

c.

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