CH 221 - Reactions and rules

What are the resonance rules?

LP alpha to pi bond

Pi alpha to pi

Pi between atoms of different electronegativities

LP alpha to carbocation

Pi bond alpha to carbocation

What is a conjugate acid?

Molecule that gains a proton after BABB

1. BH₂ * THF

2. H₂O₂ , NaOH

Adds OH to less substituted C, Anti-Markovnikov

mCPBA

Creates epoxide on alkene, Syn addition

Light or heat, HBr, ROOR

Adds Br to less substituted C, Anti-Markovnikov

Br₂ , H₂O

Adds Br to less substituted C and OH to more substituted C, Anti-addition

HBr

Adds Br to more substituted C, Markovnikov

H₂ , Pd/C

Adds H to both ends of an alkene, Syn addition

H₂O, cat H₂SO₄

Adds OH to the more substituted C, Markovnikov

Br₂

Adds Br to both ends of the alkene, Anti-addition

H₂, Lindlar’s catalyst

Turns a triple bond into a double bond by adding Hydrogens, only creates cis alkenes

What are the reactants for SN1 and E1?

OH and H₂O

Deprotonate

acid pKa higher than base pKa

Protonate

acid pKa lower than base pKa