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CHE3703 - Organic Chemistry III
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CHE3703 - Organic Chemistry III All previous years questions and answers explained.
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CHE3703Organic
Chemistry III
, CHE3703/201/2/2019
Tutorial Letter 201/2/2019
Organic Chemistry (III)
CHE3703
Semesters 2
Department of Chemistry
This tutorial letter contains assignment 02 keys.
, CHE3703/201/2/2019
QUESTION 1
1.1
H O Nu
H O H O H O
Nu
N O N O N O
O N O O O
O
The nitro group is strongly electron withdrawing by both inductive effect and resonance effect,
and it pulls electrons away from the ring making it electron poor and therefore electron
withdrawing. The ring, in turn, withdraws electrons from the carbonyl group making the
carbonyl carbon electron poor and therefore strongly electrophilic for attack by a nucleophile.
H O H O H O Nu
O
H
Nu
OCH3 OCH3 OCH3 OCH3
The methoxy group is moderately electron donating by inductive effect and strongly donating
by resonance effect. The methoxy group pushes the electron density towards the ring by
inductive effect operating through the sigma bond making it electron rich. Oxygen of the
methoxy group donates a pair of electrons towards the ring by resonance effect operating
through pi bonds and become positively charged. The ring becomes electron rich with one of
the resonance hybrids having adjacent opposite charges. This resonance hybrid is neutral and
therefore poorly electrophilic.
(8)
2
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