Answered: Consider the reaction scheme below.…

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

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions

Section19.SE: Something Extra

Problem 50MP

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Concept explainers

Organometallic Compounds of s- and p- block elements

Organometallic compounds have a minimum of one bond between a metal compound and a carbon atom. Metalloid elements such as silicon, tin, and boron form organometallic compounds which can be utilized in a few commercial chemical reactions.

Question

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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