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Q. What will be the decreasing order of stability of following carbocations ?Chemistry Question Image

UPSEEUPSEE 2016Organic Chemistry – Some Basic Principles and Techniques

Solution:

Structure (I) is aromatic.

Structure (II) shows $-1$ effect due to presence of $N \left( CH _{3}\right)_{3}$ group, which destabilises the carbocation.

Structure (III) shows $-1$ and R-effects, which destabilises the carbocation more.

Structure (IV) contains positive charge on its ring. Hence, it is less stable than structures I, II and III.

Structure (V) contains positive charge with triple bond, which has high tendency to gain electrons. Hence, it is least stable among all.

$\therefore $ Decreasing order of stability

$I\, >\, II >\, III \, >\,IV >\, V$