Chapter 9: Problem 58
Using your roadmap as a guide, show how to convert cyclohexane into
hexanedial. Show all reagents and all molecules synthesized along the way.
Chapter 9: Problem 58
Using your roadmap as a guide, show how to convert cyclohexane into
hexanedial. Show all reagents and all molecules synthesized along the way.
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Get started for freeThe reaction of 1-bromopropane and sodium hydroxide in ethanol occurs by an \(\mathrm{S}_{\mathrm{N}} 2\) mechanism. What happens to the rate of this reaction under the following conditions? (a) The concentration of \(\mathrm{NaOH}\) is doubled. (b) The concentrations of both \(\mathrm{NaOH}\) and 1-bromopropane are doubled. (c) The volume of the solution in which the reaction is carried out is doubled.
When cis-4-chlorocyclohexanol is treated with sodium hydroxide in ethanol, it gives mainly the substitution product trans-1,4-cyclohexanediol (1). Under the same reaction conditions, trans-4-chlorocyclohexanol gives 3-cyclohexenol (2) and the bicyclic ether (3).
The Williamson ether synthesis involves treatment of a haloalkane with a metal
alkoxide. Following are two reactions intended to give benzyl tert-butyl
ether. One reaction gives the ether in good yield and the other reaction does
not. Which reaction gives the ether? What is the product of the other
reaction, and how do you account for its formation?
(a)
Complete the following nucleophilic substitution reactions. In each reaction, show all electron pairs on both the nucleophile and the leaving group.
Show how you might synthesize the following compounds from a haloalkane and a nucleophile:
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