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Assignment 4

The assignment focuses on aromatic nucleophilic substitution reactions, requiring students to arrange various compounds by their reactivity with NaOMe, predict products of specified reactions, and explain observed reaction rates for halogens. It includes multiple parts, each addressing different aspects of nucleophilic aromatic substitution. Students are expected to provide justifications for their predictions and explanations.

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Shyam Kumar
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2 views

Assignment 4

The assignment focuses on aromatic nucleophilic substitution reactions, requiring students to arrange various compounds by their reactivity with NaOMe, predict products of specified reactions, and explain observed reaction rates for halogens. It includes multiple parts, each addressing different aspects of nucleophilic aromatic substitution. Students are expected to provide justifications for their predictions and explanations.

Uploaded by

Shyam Kumar
Copyright
© © All Rights Reserved
Available Formats
Download as PDF, TXT or read online on Scribd
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Assignment - 4

CY1001: Aromatic Nucleophilic Substitution

(1) Arrange the following in the increasing rate of nucleophilic aromatic substitution reaction
with NaOMe.
NO 2 O2N NO 2
NO 2

Cl Cl Cl NO 2
Cl Cl
NO 2 NO 2

(2) Predict the product(s) for the following reaction. Justify.


D
Br NaNH 2
?
liq.NH 3

(3) Predict the major product for the following reactions

aq. NaOH
F Cl + Ph-SH
Δ
NO 2
a)

OMe
NaNH3
Liq. NH3
b) Cl

Cl KNH 2
H
N Liq. NH 3
CN
c) O

NH 2
C5H11 ONO MeOH
H+ heat
COOH (source of HNO 2)
d)

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O
F CO2Et
NH
+
F N N
Me

e)

NO2
Cl NaOH

OH
f)

(4) Explain the observation for the following reaction. The relative rates for X = Cl, Br, I,
and F are 4.3, 3.3, 1.0, and 3300, respectively.

X
N
+
O2N NO2 N
H
O2N NO2

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