Chapter 22: Q12P (page 1161)
Propose a mechanism for the reaction of cyclohexyl methyl ketone with excess bromine in the presence of sodium hydroxide.
Chapter 22: Q12P (page 1161)
Propose a mechanism for the reaction of cyclohexyl methyl ketone with excess bromine in the presence of sodium hydroxide.
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Get started for freeShow how an acetoacetic ester synthesis might be used to form a δ -diketone such as heptane-2,6-dione.
Propose a mechanism for the conjugate addition of a nucleophile (Nuc:-) to acrylonitrile (H2C=CHCN) and to nitroethylene. Use resonance forms to show how the cyano and nitro groups activate the double bond toward conjugate addition.
The Knoevenagel condensation is a special case of the aldol condensation in which an active methylene compound reacts with an aldehyde or ketone, in the presence of a secondary amine as a basic catalyst, to produce a new C=C. Show the starting materials that made each of these by a Knoevenagel condensation.
Predict the products of the following reactions.
a. Cyclopentanone +Br2 in acetic acid
b. 1phenylethanol + I2 excess
c.
d)
e)
f)
g)
h)
i)
In Solved Problem 22-9, the target molecule was synthesized using a Michael addition to form the bond that is to the upper carbonyl group. Another approach is to use a Michael addition to form the bond that isto the other (lower) carbonyl group. Show how you would accomplish this alternative synthesis.
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