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General Organic Chemistry III: Reaction Intermediates
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Carbocations: formation, stability, rearrangements
JEE Advanced level
One or more correct options
Difficulty 3 of 3
g3049
Which of the following cations are aromatic (planar, cyclic, fully conjugated, with
4
n
+
2
pi electrons)?
A
the cyclobutadiene dication,
C
X
4
H
X
4
X
2
+
(planar ring, 2 pi electrons)
B
cycloprop-2-en-1-ylium (cyclopropenyl cation),
C
X
3
H
X
3
X
+
C
cyclopenta-2,4-dien-1-ylium (cyclopentadienyl cation),
C
X
5
H
X
5
X
+
D
cyclohepta-2,4,6-trien-1-ylium (tropylium),
C
X
7
H
X
7
X
+
Answer: A, B, D
Cyclopropenyl has 2 pi electrons (
n
=
0
) and tropylium has 6 (
n
=
1
), so both are aromatic. The planar
C
X
4
H
X
4
X
2
+
has 2 pi electrons, so it is aromatic too. The cyclopentadienyl cation has 4 pi electrons (
4
n
), so it is antiaromatic.
Practice General Organic Chemistry III: Reaction Intermediates
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