orgo sn1 sn2

Chemistry 241 with Ngassa at Grand Valley State University

About this deck

By: Joe Mckeever
Textbook:

Organic Chemistry: Structure and Reactivity
Created: 2010-11-10
Size: 53 flashcards
Views: 104

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Sn 2 1

-inversion of config. R to S or S to R

Sn2 2

-rate=k[nu:-][substrate]

Sn2 3

-strong n:-

Sn2 4

-polar APROTIC solvent (no OH or NH)

Sn2 and Sn1

-better LG = faster rxn

Sn1 1

-rate=k[substrate]

Sn1 2

-planar carbo+ intermediate (2nd step)

Sn1 4

-racemization at stereocenter

Sn1 5

-polar PROTIC solvent (contain OH or NH)

Sn1 6

-weak nu:-

electro-

increases across chart
decrease down chart

polar APROTIC solvent 1

sn2

polar PROTIC solvent 1

sn1

polar APROTIC solvent 2

does not contain NH or OH

polar APROTIC solvent 3

do not have a proton on an electro- atom

polar APROTIC solvent 4

can react w/ cations [+] but not anions [-]

polar PROTIC solvent 2

contains NH or OH

polar PROTIC solvent 3

bond w/ nu:- anions lowering nucleophilicity and decreasing sn2

polar PROTIC solvent 4

proton connected to an electro- atom

Nucleophile

An atom ion or molecule that has an electron pair that may be donated in bonding to an electrophile or lewis acid

acid

proton donor

base

proton acceptor

polar PROTIC solvent 5

H2O HCO2H CH3OH CH3CO2H

polar APROTIC solvent 5

DMF DMSO DME THF

Inductive Effect 1

elctronic effects through sigma bonds

Inductive Effect 2

the more alkyl groups present = the more the carbo+ charge is spread therefore more stable

Hyperconjugation 1

stabalizing a carbo+ w/ e- from an adjacent bonding orbital

Hyperconjugation 2

delocalization of charge by the overlap of an empty p orbital w/ an adjacent sigma bond

Hyperconjugation 3

overlap spreads the + charge over a larger volume stabalizing carbo+

Neighboring Group Participation 1

an internal nucleophile on the beta-carbon can participate in the departure of the LG

Phase Transfer Catalysis 1

transfers ions from an aqueous phase into an organic phase and vice versa

Phase Transfer Catalysis 2

both hydrophilic and hydrophobic

overall order of stabalization

benzylic + allylic>3*>allylic>2*>1*>methyl>vinylic

Vinyl halides

halogen on an sp2 carbon

Alkene stability

mono<di<tri<tetra

geometric isomers

diastereomers

E rotation 1

higher priority groups are on opposite sides

Z rotation 1

higher priority groups are on same sides

stability of alkenes 1

trans is more stable due to less steric interaction

steric hinderance

the structure or reactivity of a molecule is affected by the physical size and proximity of neighbouring parts of the molecule

stability of alkenes 2

major product is the more substituted alkene (one with most R groups)

E2 1

most efficient with big strong bulky bases

E2 2

hydrogen and halogen leaving must be trans if stereochemistry is involved

E2 3

halogen must be axial to leave the benzene ring

1* strong nucleophile

Sn2

1* strong bulky base

2* strong base and nucleophile

Sn2 + E2

2* strong bulky base

2* Weak base and nucleophile

Sn1 + E1

3* Weak base and nucleophile