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Flashcards in 33 Deck (13):
1

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

2

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

3

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-

4

protic solvents

SN1: protic WATER, Alcohols

SN2 = aprotic: acetone, DMF, DMSO

5

common oxidizing agents (Cr, Mn)

form ketones from secondary alcohols

the agent removes an H atom from the C bearing the -OH group

6

acidic alpha hydrogens and nucleophilic attack

nucleophilic attack = nucleophile attacks a partially positive electrophile

7

ketone-enol tautomerism

ketone is favored

does NOT require base; water will deprotonate the alpha hydrogen

8

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

9

Grignard and lithium reagents = organometallic reagents = electron RICH with anionic carbon that function as strong base

must be applied in APROTIC envrionments

nucleophilic addition

10

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

11

imine formation

replaces the ketone with a double-bonded C=N-R'

12

imine formation

replaces the ketone with a double-bonded C=N-R'

13

enolate

resonance form of deprotonated alpha carbon of ketone/aldehyde

negatively charged and NUCLEOPHILIC