Which intermediate is most stable?

Build an intermediate by putting H or CH3 on a charged carbon; +I arrows and C–H hyperconjugation overlaps with the empty p orbital are drawn and counted, with a stability meter; a toggle switches to a radical or a pyramidal carbanion.

Make the most stable carbocation (tert-butyl, 9 α-H) and then the most stable carbanion (methyl); goal checks both.

Carbanion stability follows the carbocation order; carbanion drawn planar.

• Inductive effect: a permanent shift of σ-bond electrons towards a more electronegative atom, polarising the chain; it weakens quickly and is usually negligible beyond three bonds.
• −I (electron-withdrawing) groups include –NO₂, –CN, –COOH, –COOR, halogens and aryloxy (–OAr); among halogens the −I effect is F > Cl > Br > I.
• +I (electron-releasing) groups are mainly alkyl groups such as –CH₃ and –C₂H₅.
• Resonance (mesomeric) effect: a permanent polarity caused by delocalisation of π electrons or lone pairs through a conjugated system.
• +R groups push electron density into the conjugated system: halogens, –OH, –OR, –OCOR, –NH₂, –NHR, –NR₂, –NHCOR.
• −R groups pull electron density out of it: –COOH, –CHO, >C=O, –CN, –NO₂.
• Electromeric effect: a temporary, complete transfer of a π-electron pair to one atom of a multiple bond, occurring only while an attacking reagent is present and disappearing when it is removed.
• +E: π electrons move to the atom to which the reagent attaches; −E: they move to the atom away from the attacking reagent.
• Hyperconjugation: delocalisation of σ electrons of a C–H bond on the carbon next to (alpha to) a carbocation or a π system; more alpha hydrogens mean more stabilisation.
• Hyperconjugation is also called no-bond resonance, and it adds to the explanation of the 3° > 2° > 1° > CH₃⁺ carbocation order and of the stability of more substituted alkenes.

Teaching this idea? Put the simulation on your own page or LMS with this code.