Organic Chemistry- Sn1, Sn2, E1, E2

3 > 2 >>>> 1….. Methyls cannot react

Sn1, E1, E2

Methyl > 1 > 2 > …….3 cannot react

Sn2

Polar protic solvents: polar solvents with protons to donate

Sn1, E1

Polar aprotic solvents: polar solvents that do not have an H bond donor

Sn2, E2

High temp

Sn1, E1, E2

low temp

Sn2

Form carbocations +

Sn1, E1

Concerted (happens at once)

Sn2, E2

Stepwise

Sn1, E1

Concerted (happens all at once)

Sn2, E2

Racemic mixtures

Sn1

Lots of possible reactions, double bond formation with methyl or hydride shift, and always give the most stable product

E1

Stereoinversion (2 products)

Sn2

I- > Br- > Cl- > F-

Sn1

F- > Cl- > Br- > I-

Sn2

NEt3

Polar aprotic solvent

DMSO

Polar aprotic solvent

acetone

Polar aprotic solvent

acetonitrile

Polar aprotic solvent

DMF

Polar aprotic solvent

H20

Polar protic solvent

MeOH

Polar protic solvent

EtOH

Polar protic solvent

acetic acid

Polar protic solvent

NaH, NaNH2

NEt3, PO tert-butyl, lithium diisopropylamide

Strong base weak Nu

NaOH, NaOMe, NaOEt

Strong base strong Nu

R-NH2, R-S, HS, CN, N3, I, Br, Cl, RSH, H2S

weak base strong Nu

H20, MeOH, EtOH, acetic acid

weak base weak Nu

H3PO4, H2SO4

strong acid terrible Nu

Strong base Weak Nu

1: E2

2: E2

3: E2

Strong base Strong Nu

1: E2 (30%) / Sn2 (70%)

2: E2 (70%) / Sn2 (30%)

3: E2

Weak Base Strong Nu

1: Sn2

2: Sn2 (90%) / Sn1 (10%)

3: Sn1

Weak base Weak Nu

1: no rx

2: Sn1 (60%) / E1 (40%)

3: Sn1 (50%) / E1 (50%)

Strong acid Terrible Nu

1: E1

2: E1

3: E1

-H20 is LG (dehydration)