Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Consider the three carbocations shown below, denoted as (i), (ii), and (iii) from left to right: Identify the correct order of their stability.
Options
- A(iii) > (ii) > (i)
- B(i) > (ii) > (iii)
- C(iii) > (i) > (ii)
- D(ii) > (iii) > (i)
Correct answer
A. (iii) > (ii) > (i)
Step-by-step solution
Carbocation stability is determined by electronic effects such as resonance (+M), hyperconjugation, and inductive effect (+I). In carbocation (i), the positive charge is on a secondary carbon. It is stabilized only by hyperconjugation (5 -hydrogens) and the +I effect of the alkyl groups. The positively charged carbon atom has an incomplete octet. In carbocations (ii) and (iii), the positively charged carbon is adjacent to a nitrogen atom. The lone pair of electrons on the nitrogen atom can be donated to the empty p