OC strong nucleophiles/ bases / E1 E2 Sn1 Sn2

-CN

strong nucleophile

weak base

-OH

sting base

strong nuclophile

-OCH3

strong base

strong nucleophile

CH3OH

Weak nuclei phill and weak base

-N3

strong nucleophile

weak base

-Cl

sting nucleophile

weak base

-Br

strong nucleophile

weak base

t-BuO

always does which rxn

strong base

weak nucleophile

E2 becz bulky base

-OCH2CH3

strong base and strong nucleophile

-OR

strong base

strong nucleophile

-I

strong nucleophile

weak base

-SH

strong nucleophile

weak base

-SR

strong nucleophile weak base

NR

strong nucleophile

Ok base

PR

strong nuchlophile weak base

Strong nucleophiles/ weak bases that do Sn2

(7)

CN

N3

Cl

Br

I

SH

SR

NR

PR

strong bases/ strong nucleophiles that can do E2 or SN2

(2)

-OH

-OR

strong bases and strong nucleophiles can do

E2 or SN2 or both

how to determine if a strong nucleophile and a strong base will do E2 or SN2 or both

E2= tertiary

Sn2= primary

E2 and Sn2 if secondary

what type of solvent is Acetone

Aprotic

what type of solvent is DMSO

Aprotic

what type of solvent is DMF

aprotic

what type of solvent is acetonitrile

aprotic

what type of solvent is ether

aprotic

what type of solvent is THF

aprotic

name all of the aprotic solvents

acetone

DHF

DMSO

THF

acetonitrile

ether

what does it mean to be protic

can H-Bond

Solvolyisis

Is sn1

aprotic strong nucleophile trend

up and to the left

protic strong nucleophile trend

down and to the left

Brief explain SN2

needs a strong nucleophile

does backside attack

inverts stereochemistry

CH3>1>2

what type of solvent is used in SN2

aprotic < preferred

can do protic

Sn2 rate law

rate = K [nuc][electrophile]

Sn1 breif explanation

leaving group leaves on its own first

carbocation forms

re arrange can occur

can do strong or weak nucleophile

can produce a racemic mix

Sn1 solvent used

prtoic

Sn1 rate law

rate= K[electro}

zatizev

remove hydrogen from the B-carbon with the least Hs (most substituted)

E2 brief explain

1 step

follows zaitzev

usually forms an alkene

H must be anti peri planar from leaving group

strong base

3>2>1

E2 rate law

Rate=K [nuc][elect]

E2 solvent

aprrotic preffered

can do protic

E2 base

must be strong base

E1 brief explain

leaving group leaves 1st

forms a carbo cation --- rearrange possible

weak or strong base comes in and takes an H following zaitzevs rule

3>2

E1 solvent

protic

things to remember about t-Buo

bulky base

always does E2

anti zaitzev

conjugation

when the double bond formed from E2 is one singe bond away from another double bond

gives stability

uses antizatizev