Heterolytic Reaction Attacks

nucleophilic attack

Lone pairs to from nucleophile to electrophile (e- deficient species)

loss of leaving group

heterolytic bond cleavage where atoms detaches from molecule, taking electrons with it

Carbocation Rearragement

movement of a carbocation from an unstable state to a more stable state through the use of various structural reorganizational "shifts" within the molecule

• Resonance is better than induction

• substituent that moves is the smaller one because that reaction will happen faster

allylic C+ (next to pi bond) > 3° > 2° > 1° > methyl group

electrophile

electron-deficient species that forms bonds with nucleophiles by accepting an electron pair

nucleophile

electron-rich species that forms a covalent bond by donating an electron pair

amphoteric

able to react both as a base and as an acid.

induction

Electronegative substituents withdraw electron density via the sigma orbital network within the molecule.

Inductive electron withdrawal stabilizes electron rich centers (e.g., anions) and destabilizes electron poor centers

(e.g., cations).

alkyl grups have the lowest withdraw strength, then halogens, then ketonesm and the strongest is nitrogen groups??

primary

carbon atom bonded to only one other carbon atom, least stable

secondary

carbon atom bonded to only two other carbon atom

most stable carbocation

allylic C+ (next to pi bond) > 3° > 2° > 1° > methyl group

hyperconjugation

hydrogen’s nearby electron density help stabilize carbocation empty p-orbital