33 Flashcards
sn2
Rear, open access, k[Nu][El], POLAR and APROTIC, no rearrangement, strong non-bulky nucleophile
SINGLE STEP
aprotic because the nucleophile should stay de-protonated = acetone, DMF, DMSO
sn2
Rear, open access, BIMOLECULAR (k[Nu][El]), POLAR and APROTIC, no rearrangement, strong non-bulky nucleophile
SINGLE STEP (no carbocation produced)
aprotic because the nucleophile should stay de-protonated; polar is good = acetone, DMF, DMSO
OH can be a leaving group
sn1
rate = k[El]
Protic is good; stabilizes the carbocation, solvates the leaving group
planar carbocation forms
water attacks forming an alcohol product (solvolysis); weaker nucleophiles prefer sn1
Rearrangement due to carbocation
alcohol attacks to form an ether -O-
protic solvents
SN1: protic WATER, Alcohols
SN2 = aprotic: acetone, DMF, DMSO
common oxidizing agents (Cr, Mn)
form ketones from secondary alcohols
the agent removes an H atom from the C bearing the -OH group
acidic alpha hydrogens and nucleophilic attack
nucleophilic attack = nucleophile attacks a partially positive electrophile
ketone-enol tautomerism
ketone is favored
does NOT require base; water will deprotonate the alpha hydrogen
ketone-enol tautomerism
ketone is favored
does NOT require base; water will deprotonate the alpha hydrogen
Does NOT work in acidic environments, or else the carbonyl oxygen of aldehyde will be protonated
Grignard and lithium reagents = organometallic reagents = electron RICH with anionic carbon that function as strong base
must be applied in APROTIC envrionments
nucleophilic addition
acetals form when aldehydes or ketones react with alcohols in the presence of acid
ACETAL = formation of TWO O-R’ groups from a ketone
methanol acts as nucleophile
imine formation
replaces the ketone with a double-bonded C=N-R’
imine formation
replaces the ketone with a double-bonded C=N-R’
enolate
resonance form of deprotonated alpha carbon of ketone/aldehyde
negatively charged and NUCLEOPHILIC
