a) Give the mechanistic symbols (SN1, SN2, E1, E2) that are most consistent with each of the following statements: Primary alkyl halides react with potassium tert-butoxide in tert-butyl alcohol mainly by thismechanism.b) State whether the equilibrium constant is greater than, less than, or equal to one, for thefollowing reaction, given the pKa of acetic acid is 4.74 and the pKa of the ammonium ion is 9.25.СH:СО2H (аq) + NH3 (аq) —> СH3CO2: (аq) + NH4* (аq) Unhindered primary alkyl halides react with sodium ethoxide in ethanol mainly by thismechanism.When cyclohexyl bromide is treated with sodium tert-butoxide in tert-butanol, the majorproduct is formed by this mechanism.The substitution product obtained by solvolysis of tert-butyl bromide in ethanol arises by thismechanism.In ethanol that contains a dilute amount of sodium ethoxide, tert-butyl bromide reacts mainly bythis mechanism.When 2-bromobutane is treated with potassium cyanide in DMSO, the major product is formedby this mechanism.

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e the mechanistic symbols (SN1, SN2, E1, E2) that are most consistent with each of the following statements:

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter19: Enolate Anions And Enamines

Section: Chapter Questions

Problem 19.40P: Enamines normally react with methyl iodide to give two products: one arising from alkylation at...

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Enamines normally react with methyl iodide to give two products: one arising from alkylation at nitrogen and the second arising from alkylation at carbon. For example, Heating the mixture of C-alkylation and N-alkylation products gives only the product from C-alkylation. Propose a mechanism for this isomerization.
Aldehydes and ketones undergo acid-catalyzed reaction with alcohols to yield hemiacetals, compounds that have one alcohol-like oxygen and one ether-like oxygen bonded to the same carbon. Further reaction of a hemiacetal with alcohol then yields an acetal, a compound that has two ether-like oxygens bonded to the same carbon. (a) Show the structures of the hemiacetal and acetal you would obtain by reaction of cyclohexanone with ethanol. (b) Propose a mechanism for the conversion of a hemiacetal into an acetal.
A problem often encountered in the oxidation of primary alcohols to acids is that esters are sometimes produced as by-products. For example, oxidation of ethanol yields acetic acid and ethyl acetate: Propose a mechanism to account for the formation of ethyl acetate. Take into account the reversible reaction between aldehydes and alcohols:
Alkynes undergo hydroboration to give alkenylboranes, which can be oxidized to give carbonyl compounds with hydrogen peroxide. The net result of the two- step sequence is hydration, which gives aldehydes from terminal alkynes. In these reactions, the alkyne is oxidized to form an enol, which then tautomerizes to a carbonyl. Draw the structure of the enol formed in the conversion of 1-hexyne to hexanal. Click and drag to start drawing a structure.
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