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alkyl halides
rxns of alkyl halides: SN1, SN2, E1, E2
30
Organic Chemistry
Undergraduate 2
01/03/2014

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Cards

Term
SN2: mechanism
Definition
concerted (1-step, no intermediate), back-side attack
Term
E2: mechanism
Definition
concerted (1-step, no intermediate), anti-coplanar
Term
SN1: mechanism
Definition
2-steps with carbocation intermediate
Term
E1: mechanism
Definition
2-steps with carbocation intermediate
Term
SN2: kinetics
Definition

rate is second order

 

rate = k[Nuc][RX]

Term
E2: kinetics
Definition

rate is second order

 

rate = k[Nuc][RX]

Term
E1: kinetics
Definition

rate is first order

 

rate = k[RX]

Term
SN1: kinetics
Definition

rate is first order

 

rate = k[RX]

Term
SN2: type of nucleophile/base
Definition
strong nucleophile
Term
SN1: type of nucleophile/base
Definition
weak nucleophile
Term
E2: type of nucleophile/base
Definition
strong base
Term
E1: type of nucleophile/base
Definition
weak base
Term
SN2: substrate trend
Definition
methyl > 1° > 2° >>> 3°
Term
SN1: substrate trend
Definition
3° > 2° >>> 1°
Term
E1: substrate trend
Definition
3° > 2° >>> 1°
Term
E2: substrate trend
Definition
3° > 2° > 1°
Term
SN2: possibility of rearrangements
Definition
impossible b/c there is no carbocation intermediate
Term
E2: possibility of rearrangements
Definition
impossible b/c there is no carbocation intermediate
Term
SN1: possibility of rearrangements
Definition
carbocation intermediate may rearrange into more stable carbocation using hydride shifts or methyl shifts
Term
E1: possibility of rearrangements
Definition
carbocation intermediate may rearrange into more stable carbocation using hydride shifts or methyl shifts
Term
E2: orientation of alkene
Definition

Zaitsev product (most-substituted alkene) results from unhindered base

 

Hofmann product (less-substituted alkene) results from sterically hindered base

Term
E1: orientation of alkene
Definition

Zaitsev product (most-substituted alkene) results from unhindered base

 

Hofmann product (less-substituted alkene) results from sterically hindered base

Term
SN2: stereochemistry
Definition
inversion of configuration
Term
SN1: stereochemistry
Definition
inversion & retention of configuration
Term
E1:  stereochemistry
Definition
no special geometry required
Term
E2: stereochemistry
Definition
anti coplanar transition state required
Term
SN2: solvent
Definition

wide variety of solvents;

 

polar aprotic solvents will increase nucleophilicity

Term
SN1:  solvent
Definition
good ionizing solvent needed
Term
E2: solvent
Definition
wide variety of solvents
Term
E1: solvent
Definition
good ionizing solvent needed
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