Organic Chemistry Substitution & Elimination (DAT)

Nucleophiles are electron-___

rich

Electrophiles are electron-___

poor

Nucleophiles ___ (accept/donate) electrons

donate

Electrophiles ___ (accept/donate) electrons

accept

Nucleophile strength ___ (increases/decreases) left to right across a row for both polar protic and polar aprotic solvents

decreases

I-, Cl-, Br-, HO-, HS-, and NC- are all examples of common

nucleophiles

H3C-CO-CH3, secondary LG, and tertiary carbocations are all examples of

electrophiles

___ ___ solvents form Hydrogen bonds

polar protic

___ ___ solvents cannot donate Hydrogen bonds

polar aprotic

For polar protic solvents, nucleophilicity increases ___ (up/down) a group

down

For polar aprotic solvents, nucleophilicity increases ___ (up/down) a group

up

Atoms that detach from the molecule, taking electrons

leaving groups

List three examples that are both nucleophiles and leaving groups

I-, Cl-, Br-

The best leaving groups are ___ ___

weak bases

The major, more substituted alkene product formed during an elimination reaction is called a ___ alkene

Zaitsev

You can produced the major, more substituted Zaitsev alkene through elimination with the following reagent(s)

H2SO4, heat

Draw the mechanism and name the product for the following reaction

but-2-ene

Is the following mechanism showing a dehydration or hydration reaction of an alcohol

dehydration

SN2 reactions are well known for their ___ ___

backside attack

SN2 reactions are ___ step(s)

one

In an SN2 reaction, stereochemistry ___ (is/is not) inverted

is

SN2 rate equation: rate =

k[nucleophile][substrate]

SN2 reactions are favored by ___ (strong/weak) nucleophiles

strong

SN2 reactions are favored by ___ (1/2/3) carbon substrate types

1

Common solvents for SN2 reactions include polar ___ solvents such as ___ and ___

aprotic

In SN___ and E___ reactions, the LG leaves once the nucleophile has attacked

2

SN1 reactions are ___ step(s)

two

SN1 reactions form a ___ mixture

racemic

SN1 reaction rate equation: rate =

k[substrate]

SN1 reactions are favored by ___ (strong/weak) nucleophiles

weak

SN1 reactions are favored by ___ (1/2/3) carbon substrate types

3

In SN___ and E___ reactions, the LG leaves on it’s own

1

In SN2, the rate determining step is the formation of the

carbocation

More stable carbocations allow SN1 reactions to happen ___ (faster/slower)

faster

Carbocation rearrangements only happen in what two reaction types

SN1 and E1

A hydride shift is the movement of a

hydrogen

E2 reactions are ___ step(s)

1

E2 reaction rate equation: rate =

k[base][substrate]

E2 reactions are favored by strong ___ ___

bulky bases

NaOEt and NaOMe are common bases for ___ reactions

E2

E2 reactions are favored by ___ (1/2/3) carbon substrate types

any

In an E2 reaction, the LG and attacking strong base must be ___

antiperiplanar

E1 reactions are ___ step(s)

2

E1 reaction rate equation: rate =

k[substrate]

E1 reactions are favored by ___ (strong/weak) bases

weak

H2O and ROH are common examples of bases that will undergo a(n) ___ reaction

E1

E1 reactions are favored by ___ (1/2/3) carbon substrate types

3

E1 reactions favor the ___ (heat/cold)

heat

The Zaitsev product is known as the ___ product

thermodynamic

The Hofmann product is known as the ___ product

kinetic

The thermodynamic product is the ___ substituted alkene

more

The thermodynamic product is favored by ___ bases

small

The kinetic product is the ___ substituted alkene

less

The kinetic product is favored by ___ bases

bulky

If the LG is primary, the only possible reactions are

SN2 and E2

If the LG is tertiary, the only possible reactions are

SN1, E1, and E2

If there is a bulky base, the reaction is

E2

If the solvent in polar protic, the only possible reactions are

SN1/E1

If heat is involved, the only possible reactions are

E1 and E2