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35 Cards in this Set

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nucleophile
good nucleophile is strong base

e- rich species that are attracted to positively polarized atoms

nucleophile strength
RO-> HO->RCO2>ROH>H2O
electrophile
gets attacted by nucleophile
partially positive
C attacted to electronegative atom
nucleophiles in protic solvent
solvent that capable of hydrogen bonding

large atoms tend to be better nucleophile

CN->I->RO->HO->Br->Cl->F->H2O
nucleophiles in aprotic solvnet
F->Cl->Br->I
SN1

unimolecular nucleophilic sub
-2 steps
-favored in protic solvent
-formation of carbocation (rate limiting step)

-rate=k[RX] RX=leaving group

-favors 3>2>1 carbon because this is order of stability for carbocation
more stable faster the rxn

-produce recemic product
have equal amt of R and S thus no optical activity

-favored with bulky nucleophiles
good leaving group
weak base makes good leaving group

toslate>I-> Br-> Cl- > F-
SN2

bimoecular nucleophillic sub
-1step
-favor aprotic solvent

-favor 1>2>3 carbon

-rate k[nuc][RX]

-produce inverted product optically active

-trigonal bypyramid transition state
trigonal bypyrimid transistion stae in which sub model?
SN2
strong nucleophile
CN>I->RCO2>RO->HO->Br>Cl->F->H2O
strong acid
HCl, H2SO4, H3PO4, HNO3
weak acid
Cl-, SO4-, PO4-, NO3-
toslate
good LG
Br
good LG
Cl
good LG
HCl
strong acid
H2SO4
Strong acid
H3PO4
Strong acid
HNo3
Strong acid
CN>I>RO>HO>Cr>Cl>F>H20
nucleophile in protc solution
F>cl>Br>I
nucleophile in aprotic solution
radicals
species with unpaired electron
what is most stable radical
CR3 > CR2H> CRH2> CH3
free radical halogentation rxn are practical only fo () and ()
br and cl
in free radical halogentaion rxn Br react () compared to cl
slowly thus more likely to react in a manner that forms most stable alkyl radical
in free radical halogenation
Cl indiscriminates and produce
several different both stable and nonstable alkyl radical
RO-
weak nucleophile
NH3
weak nucleophile
aprotic is needed in SN2 bc

how does H bond affect nu- in in protic during SN1
no H-bond means Nu- naked and free to atack electrophile(rate det. step)

in SN1 protic, Hbond works with Nu- but less then SN2 bc Nu is not in rate det. step
OH-
strong nuceophile
CN-
strong nucleophlile
NH2-
strong nucleophile
vinylic proton
proton that is attach to the double bond
alcohol and strong acid like H2SO4 lead to
elimination
strong base with
3, 2, 1, alklyl halide
3- E1
2- E2
1- E2/Sn2
weak base with
3, 2, 1, alklyl halide
3-Sn1/E1 in protic
2-Sn2 in aprotic
1-Sn2