Sublimation / Elimination

What is a good leaving group?

Pka of conj. acid < 0

What is a good nucleophile?

negatively charged

What is a strong base?

pka of conj. acid >11

Poor Nuc / Weak Base

Methyl

SN2

Poor Nuc / Weak Base

1

SN2

Poor Nuc / Weak Base

2

SN1

E1 Δ

Poor Nuc / Weak Base

3

SN1

E1 Δ

Good Nuc / Weak Base

Methyl

SN2

Good Nuc / Weak Base

1

SN2

Good Nuc / Weak Base

2

SN2

Good Nuc / Weak Base

3

SN1

E1 Δ

Good Nuc / Strong Base

Methyl

SN2

Good Nuc / Strong Base

1

SN2

E2 (bulky)

Good Nuc / Strong Base

2

E2

Good Nuc / Strong Base

3

E2

What is the zaitsev product?

Most substituted alkene

What is the hoffman product?

least substituted alkene

When will Hoffman be the major product?

when there are bulky bases

How do protic solvents effect SN1/E1 and SN2/E2?

SN1/E1 → Lowers energy of REACTANTS, slows down rxn

SN2/E2 → Lowers energy for RDS, encourages leaving group to leave

How do aprotic solvents effect SN1/E1 and SN2/E2

SN1/E1 → no effect

SN2/E2 → no effect!