3. a. The reaction sequence shown in Figure 4 demonstrates the synthesis of a disubstituted benzene derivative O from compound M through two Electrophilic Aromatic Substitution reactions. C6H5Cl M CI AICI3 G N Figure 4 HNO3, H₂SO4 C₂H6CINO3 O (i) Draw the chemical structure of compound M. (ii) Draw the mechanism for the transformation of compound M to intermediate N using curly arrows. (iii) Draw the chemical structure of compound O.

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
Chapter11: Ethers, Epoxides, And Sulfides
Section: Chapter Questions
Problem 11.37P: Following are the steps in the industrial synthesis of glycerin. Provide structures for all...
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3. a.
(i)
The reaction sequence shown in Figure 4 demonstrates the synthesis of a
disubstituted benzene derivative O from compound M through two Electrophilic
Aromatic Substitution reactions.
(ii)
C6H5Cl
M
CI
AICI3
2
N
Figure 4
HNO3, H₂SO4
CaH6CINO3
O
Draw the chemical structure of compound M.
Draw the mechanism for the transformation of compound M to intermediate N
using curly arrows.
(iii)
Draw the chemical structure of compound O.
(iv) Draw the mechanism for the transformation of intermediate N to compound O
using curly arrows.
(v) Account for the regiochemical outcome observed in compound O.
Transcribed Image Text:3. a. (i) The reaction sequence shown in Figure 4 demonstrates the synthesis of a disubstituted benzene derivative O from compound M through two Electrophilic Aromatic Substitution reactions. (ii) C6H5Cl M CI AICI3 2 N Figure 4 HNO3, H₂SO4 CaH6CINO3 O Draw the chemical structure of compound M. Draw the mechanism for the transformation of compound M to intermediate N using curly arrows. (iii) Draw the chemical structure of compound O. (iv) Draw the mechanism for the transformation of intermediate N to compound O using curly arrows. (v) Account for the regiochemical outcome observed in compound O.
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