Sn1 Flashcards by Molly Gallagher | Brainscape

Q

what does Sn1 stand for

A

substitution, nucleophilic, unimolecular

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Q

how many steps?

A

2

L.G. leaves (rate determining) (carbocation formed)

Nu attacks

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Q

rate rxn

A

rate = k[substrate] concentration dependent

rate depends on E of t.s. 1

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Q

solvolysis, hydrolysis

A

rxn where solvent is also Nu

H solvent is hydrolysis

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Q

how many t.s.?

A

2

rxn exothermic overall

carbocation formation is endothermic

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Q

is Sn1 stereospecific?

A

no, produces racemic mixture

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Q

Nu

A

any Nu reacts at same rate (does not need to be good)

F- still doesn’t work, trapped by solvent

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Q

substrate

A

usually R-X but can be R-OH

good L.G. increases rate (H2O is great)

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Q

if L.G. is a strong base

A

can perform Sn1 under acidic conditions

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Q

Hammond Postulate

A

late t.s. helps stabilize carbocation

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Q

stability of carbocation

A

hyperconjugation of CH3 groups stabilizes

late t.s. stabilizes

benzylic & allylic > 3rd > 2nd > 1st > methyl

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Q

solvent effects

A

polar protic increases rate

stabilizes carbocation by reducing Ea

helps L.G. leave by attracting it

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