In which pairs, the first ion is more stable than the second?
- (A) & (B) only
- (B) & (D) only
- (A) & (C) only
- (B) & (C) only
Answer
(1) (A) & (B) only
Solution
(A) In the first ion the lone pair of –OMe oxygen delocalises onto C (+R), giving a structure in which every atom has an octet ( O=C), while the second has only +I and hyperconjugation of –Me. So the first is more stable. ✓
(B) The first is a carbanion conjugated with the benzene ring bearing an ortho –NO2 group, so the negative charge is delocalised onto the ring and the nitro oxygens (–R, –I) and it is highly stabilised. The second is a carbocation attached to a ring bearing an ortho –NO2 group, whose –R and –I effects destabilise the positive charge. So the first is more stable. ✓
(C) The first is a primary carbocation (only +I / hyperconjugation), while in the second the CH2 is attached to a C=C (allylic carbocation) and is stabilised by resonance. So the second is more stable. ✗
(D) The first is the tert-butyl carbocation (+I and 9 hyperconjugating H), while in the second –OMe on C gives +R stabilisation, which outweighs hyperconjugation. So the second is more stable. ✗
(A) & (B) only.
Answer: (1)