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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Question

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 this
mechanism.
b) State whether the equilibrium constant is greater than, less than, or equal to one, for the
following 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 this
mechanism.
When cyclohexyl bromide is treated with sodium tert-butoxide in tert-butanol, the major
product is formed by this mechanism.
The substitution product obtained by solvolysis of tert-butyl bromide in ethanol arises by this
mechanism.
In ethanol that contains a dilute amount of sodium ethoxide, tert-butyl bromide reacts mainly by
this mechanism.
When 2-bromobutane is treated with potassium cyanide in DMSO, the major product is formed
by this mechanism.

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