Consider the reaction scheme below. PhLi HONH,, HCI A ELOH B D (i) Deduce the structures of compounds A, D and intermediate C. (ii) Outline the mechanism for the conversion of A to B. 2)
Consider the reaction scheme below. PhLi HONH,, HCI A ELOH B D (i) Deduce the structures of compounds A, D and intermediate C. (ii) Outline the mechanism for the conversion of A to B. 2)
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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![а)
Consider the reaction scheme below.
PhLi
HONH,, HCI
A
ELOH
B
(i)
Deduce the structures of compounds A, D and intermediate C.
(ii)
Outline the mechanism for the conversion of A to B.
b) Pyrrole and indole both react with the reagents shown below to give compounds E
and F respectively.
Reagents:
POC13, NazCO3, H2O
N.
E
F
(i)
(ii)
(iii)
Show how the electrophile is generated.
Account for the regioselectivity observed.
Complete the mechanism for the formation of compound F.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F72b28a69-75ea-4f82-b47b-d872deab4066%2Fe8c2223f-167d-4f8d-8dd1-ad85cbafca3b%2Ftsk5lrzd_processed.jpeg&w=3840&q=75)
Transcribed Image Text:а)
Consider the reaction scheme below.
PhLi
HONH,, HCI
A
ELOH
B
(i)
Deduce the structures of compounds A, D and intermediate C.
(ii)
Outline the mechanism for the conversion of A to B.
b) Pyrrole and indole both react with the reagents shown below to give compounds E
and F respectively.
Reagents:
POC13, NazCO3, H2O
N.
E
F
(i)
(ii)
(iii)
Show how the electrophile is generated.
Account for the regioselectivity observed.
Complete the mechanism for the formation of compound F.
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