Bases and Nucleophiles

E2 happens in...

One step

NaOH

Strong base weak nucleophile

Strong base weak nucleophiles make what reactions?

1° ~ E2

2° ~ E2

3° ~ E2

Weak base strong nucleophiles make what reactions?

1° SN2

2° SN2

3° SN1

RS-

Weak base strong nucleophile

HO-

Strong base strong nucleophile

NaH

Strong base weak nucleophile

Cl-

Weak base strong nucleophile

MeO-

Strong base strong nucleophile

Br-

Weak base strong nucleophile

HS-

Weak base strong nucleophile

MeONa / NaOMe

Strong base strong nucleophile

DBU

Strong base weak nucleophile

tBuOK

Strong base weak nucleophile

DBN

Strong base weak nucleophile

H2S

Weak base strong nucleophile

H2O

Weak base weak nucleophile

EtOH

Weak base weak nucleophile

MeOH

Weak base weak nucleophile

Weak base weak nucleophiles make what reactions?

1° none

2° none

3° 50% SN1 and 50% E1

EtO-

Strong base strong nucleophile

EtONa / NaOEt

Strong base strong nucleophile

Strong base strong nucleophiles make what reactions?

1° 30% E2 and 70% SN2

2° 70% E2 and 30% SN2

3° E2

RSH

Weak base strong nucleophile

H2SO4

Weak base weak nucleophile

I-

Weak base strong nucleophile

Slow reactions mean what in terms of products?

They make one product

Fast reactions mean what in terms of products?

They make two products

Equation for optical purity (ee)

samples optical rotation/pure optical rotation