The reaction sequence shown in Scheme 5 demonstrates the synthesis of a substituted benzene derivative Q. NH2 NANO2, HCI HNO,, H,SO, CHSCIN2 CHINO 0°C Scheme 5 Draw the structure of intermediate O. (i) Draw the mechanism for the transformation of aniline N to intermediate O. (ii) Identify the reagent X used to convert compound O to the iodinated compound Р. (iv) Identify the possible structures of compound Q.

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
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.42P: When cis-2-decalone is dissolved in ether containing a trace of HCl, an equilibrium is established...
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The reaction sequence shown in Scheme 5 demonstrates the synthesis of a
substituted benzene derivative Q.
NH2
NANO,, HCI
HNO,, HSO,
CoHsCIN2
CH,INO,
0°C
N
Q
Scheme 5
Draw the structure of intermediate O.
(ii)
Draw the mechanism for the transformation of aniline N to intermediate O.
(iii) Identify the reagent X used to convert compound O to the iodinated compound
Р.
(iv) Identify the possible structures of compound Q.
(v)
Draw the mechanism for the transformation of intermediate P to compound Q.
(vi)
Account for the regiochemical outcome observed in the reaction forming
compound Q.
Transcribed Image Text:The reaction sequence shown in Scheme 5 demonstrates the synthesis of a substituted benzene derivative Q. NH2 NANO,, HCI HNO,, HSO, CoHsCIN2 CH,INO, 0°C N Q Scheme 5 Draw the structure of intermediate O. (ii) Draw the mechanism for the transformation of aniline N to intermediate O. (iii) Identify the reagent X used to convert compound O to the iodinated compound Р. (iv) Identify the possible structures of compound Q. (v) Draw the mechanism for the transformation of intermediate P to compound Q. (vi) Account for the regiochemical outcome observed in the reaction forming compound Q.
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