orgo 1 exam 2 flashcards

LG ranking

Cl, Br, I, Ots, OMs, OTF, positive LG - weak base=good LG

draw reaction chart

correct?

does heat favor sn1 or e1

e1

Strong base, weak nucleophile

Kot-bu, LDA

strong base, strong nuc

NaOH, NaNH2

weak base, strong nucleophile

X-, NaCN, NaSH, N3

weak base, weak nuc

H2O, MeOH, EtOH, amides

Polar protic solvents and what to they favor

H2O, ROH -favor 1

stabilize formation of C+, makes nucleophile worse

polar Aprotic solvents and what do they favor

acetone, DMSO, DMF, THF - favor 2

C+ wont form, makes nucleophile better

sn1 mechanism with carbocation intermediate

sn2 mechanism

with carbocation intermediate

E1 mechanism

e2 mechanism

- needs strong hindered base, LG must be axial and be anti-peri planar to H

major will be zaitssev unless base is bulky

KOtbu & LDA prefer less substituted

strong base weak nuc

primary LG

secondary LG

Tertiary LG

E2 requirements

strong base strong nuc

primary LG

secondary LG

Tertiary LG

Sn2

E2

E2

weak base strong nuc

primary LG

secondary LG

Tertiary LG

SN2

SN2

Sn1

weak base weak nuc

primary LG

secondary LG

Tertiary LG

no rxn - unless stabilized

Sn1/E1

SN1/E1

neuman projection

top left =

top right =

neuman projection

dash

wedge

chair conformation

wedge =

dash =

wedge = up

dash = down

order of carbocation rearrangement

Ring expansion

hydride shift

1, 3 methyl shift

ring expansion criteria

C+ next to 3,4,5 membered ring

hydride shift

C+ next to tertiary carbon

methyl shift

C+ next to 4 carbon w/ methyl group

Draw E2 reaction diagram

draw e1 diagram

sn1 diagram

sn2 diagram