Chapter 9: Problem 20
Each carbocation is capable of rearranging to a more stable carbocation. Limiting yourself to a single 1,2 -shift, suggest a structure for the rearranged carbocation.
Chapter 9: Problem 20
Each carbocation is capable of rearranging to a more stable carbocation. Limiting yourself to a single 1,2 -shift, suggest a structure for the rearranged carbocation.
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Get started for freeSolvolysis of the following bicyclic compound in acetic acid gives a mixture of products, two of which are shown. The leaving group is the anion of a sulfonic acid, \(\mathrm{ArSO}_{3} \mathrm{H}\). A sulfonic acid is a strong acid, and its anion, \(\mathrm{ArSO}_{3}{ }^{-}\), is a weak base and a good leaving group. Propose a mechanism for this reaction. \(\mathrm{O}\)
Treatment of 1 -aminoadamantane, \(\mathrm{C}_{10} \mathrm{H}_{17} \mathrm{~N}\), with methyl 2,4-dibromobutanoate in the presence of a nonnucleophilic base, \(R_{3} N_{\text {, involves two successive }} S_{N} 2\) reactions and gives compound A. Propose a structural formula for compound A.
The 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.
1-Chloro-2-butene undergoes hydrolysis in warm water to give a mixture of these allylic alcohols. Propose a mechanism for their formation.
Write the expected substitution product(s) for each reaction and predict the
mechanism by which each product is formed.
(a)
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