Organic Chemistry - Substitution/elimination

Front 1

Sn1 Substrate Hierarchy

Back 1

3° > 2° > 1°

Front 2

Sn2 Substrate Hierarchy

Back 2

1° > 2° > 3°

Front 3

Sn1 Requirement: Nucleophile

Back 3

N/A - Irrelevant

Front 4

Sn2 Requirement: Nucleophile

Back 4

Strong Base

Front 5

Sn1 Requirement: Leaving Group

Back 5

Weak Base

Front 6

Sn2 Requirement: Leaving Group

Back 6

Weak Base

Front 7

Sn1 Requirement: Solvent

Back 7

Polar PROTIC

Front 8

Sn2 Requirement: Solvent

Back 8

Polar aPROTIC

Front 9

Sn1 stereochemistry:

Back 9

Racemic

Front 10

Sn2 stereochemistry:

Back 10

Inversion

Front 11

E1 Stereochemistry:

Back 11

N/A

Front 12

E2 Stereochemistry:

Back 12

Anti

Front 13

E1 Substrate Hierarchy

Back 13

Allylic > 3° > 2° > 1°

Front 14

E2 Substrate Hierarchy

Back 14

3° > 2° > 1°

Front 15

E1 Nucleophile:

Back 15

Weak Nuc/base

Front 16

E2 Nucleophile:

Back 16

Strong Base

Front 17

E1 Leaving Group:

Back 17

Weak Base

Front 18

E2 Leaving Group:

Back 18

Good Base

Front 19

E1 Solvent

Back 19

Polar PROTIC

Front 20

E2 Solvent

Back 20

Polar aPROTIC

Front 21

Solvent: aprotic
Substrate: 3°
Base/Nuc: Good
Leaving Group: Good

Back 21

E2
Base/Nuc & Leaving group are N/A

Front 22

Solvent: aprotic
Substrate: 1°
Base/Nuc: Good Nuc/ Weak Base
Leaving Group: Good

Back 22

Sn2

Front 23

Solvent: aprotic
Substrate: 1°
Base/Nuc: Strong Base
Leaving Group: Good

Back 23

Sn2

Front 24

Solvent: aprotic
Substrate: 1°
Base/Nuc: Strong & Hindered
Leaving Group: Good

Back 24

E2

Front 25

Solvent: aprotic
Substrate: 2°
Base/Nuc: Good Nuc/ Weak Base
Leaving Group: Good

Back 25

Sn2

Front 26

Solvent: aprotic
Substrate: 2°
Base/Nuc: Strong
Leaving Group: Good

Back 26

E2

Front 27

Solvent: protic
Substrate: 1°
Base/Nuc: Strong Hindered Base
Leaving Group: Good

Back 27

E2

Front 28

Solvent: protic
Substrate: 1°
Base/Nuc: Strong Base
Leaving Group: Good

Back 28

Sn2

Front 29

Solvent: protic
Substrate: 1°
Base/Nuc: Good Nuc
Leaving Group: Good

Back 29

Sn2

Front 30

Solvent: protic
Substrate: 2°
Base/Nuc: Strong Base
Leaving Group: Good

Back 30

E2

Front 31

Solvent: protic
Substrate: 2°
Base/Nuc: Good Nuc/Weak Base
Leaving Group: Good

Back 31

Sn2/Sn1

Front 32

Solvent: protic
Substrate: 2°
Base/Nuc: Weak Nuc/Weak Base
Leaving Group: Good

Back 32

Sn1/E1

Front 33

Solvent: protic
Substrate: 3°
Base/Nuc: Strong Base
Leaving Group: Good

Back 33

E2

Front 34

Solvent: protic
Substrate: 3°
Base/Nuc: Weak Nuc/Weak Base
Leaving Group: Good

Back 34

Sn1/E1

Front 35

Solvent: protic
Substrate: 3°
Base/Nuc: Good Nuc/Weak Base
Leaving Group: Good

Back 35

Sn1

Front 36

Because E2 mechanism results in formation of a ___ bond, the two leaving groups (often a _____ and a ______) need to be ______ & _____

Back 36

Because E2 mechanism results in formation of a _pi_ bond, the two leaving groups (often a _hydrogen_ and a _halogen_) need to be _anti_ & _coplanar_

Front 37

The reaction rate of E2, influenced by both the alkyl halide and the base, is _____ order.

Back 37

The reaction rate of E2, influenced by both the alkyl halide and the base, is _second_ order.

Front 38

E1 Reactions mostly occurs in complete absence of ____ or presence of only a weak ____

Back 38

E1 Reactions mostly occurs in complete absence of _base_ or presence of only a weak _base_

Front 39

E1 reactions [do/do not] need the leaving groups to be anti & coplanar

Back 39

E1 reactions _do not_ need the leaving groups to be anti & coplanar

Front 40

the Sn2 reaction rate depends on the concentration of both the _______ and _______

Back 40

the Sn2 reaction rate depends on the concentration of both the _substrate_ and _nucleophile_

Front 41

Sn1 Rate Equation

Back 41

r=k[substrate]

Front 42

As steric hindrance around the electrophilic center increases, _______ is disfavored and _______ is the predominant reaction

Back 42

As steric hindrance around the electrophilic center increases, _substitution_ is disfavored and _elimination_ is the predominant reaction

Front 43

Stronger base favors [Sn2/E2]

Back 43

Stronger base favors [E2]

Front 44

Sn2 Rate Equation

Back 44

r=k[substrate][nucleophile]

Front 45

E1 Regiochemistry

Back 45

Bulky Base: Hoffman
Non-bulky Base: Zaitsev

Front 46

E2 Regiochemistry

Back 46

Bulky Base: Hoffman
Non-bulky Base: Zaitsev