Ochem Subject Test 1 And 2 "sub Rxn"

Front 1

nucleophile

Back 1

good nucleophile is strong base

e- rich species that are attracted to positively polarized atoms

nucleophile strength
RO-> HO->RCO2>ROH>H2O

Front 2

electrophile

Back 2

gets attacted by nucleophile
partially positive
C attacted to electronegative atom

Front 3

nucleophiles in protic solvent

Back 3

solvent that capable of hydrogen bonding

large atoms tend to be better nucleophile

CN->I->RO->HO->Br->Cl->F->H2O

Front 4

nucleophiles in aprotic solvnet

Back 4

F->Cl->Br->I

Front 5

SN1

unimolecular nucleophilic sub

Back 5

-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

Front 6

good leaving group

Back 6

weak base makes good leaving group

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

Front 7

SN2

bimoecular nucleophillic sub

Back 7

-1step
-favor aprotic solvent

-favor 1>2>3 carbon

-rate k[nuc][RX]

-produce inverted product optically active

-trigonal bypyramid transition state

Front 8

trigonal bypyrimid transistion stae in which sub model?

Back 8

SN2

Front 9

strong nucleophile

Back 9

CN>I->RCO2>RO->HO->Br>Cl->F->H2O

Front 10

strong acid

Back 10

HCl, H2SO4, H3PO4, HNO3

Front 11

weak acid

Back 11

Cl-, SO4-, PO4-, NO3-

Front 12

toslate

Back 12

good LG

Front 13

Br

Back 13

good LG

Front 14

Cl

Back 14

good LG

Front 15

HCl

Back 15

strong acid

Front 16

H2SO4

Back 16

Strong acid

Front 17

H3PO4

Back 17

Strong acid

Front 18

HNo3

Back 18

Strong acid

Front 19

CN>I>RO>HO>Cr>Cl>F>H20

Back 19

nucleophile in protc solution

Front 20

F>cl>Br>I

Back 20

nucleophile in aprotic solution

Front 21

radicals

Back 21

species with unpaired electron

Front 22

what is most stable radical

Back 22

CR3 > CR2H> CRH2> CH3

Front 23

free radical halogentation rxn are practical only fo () and ()

Back 23

br and cl

Front 24

in free radical halogentaion rxn Br react () compared to cl

Back 24

slowly thus more likely to react in a manner that forms most stable alkyl radical

Front 25

in free radical halogenation
Cl indiscriminates and produce

Back 25

several different both stable and nonstable alkyl radical

Front 26

RO-

Back 26

weak nucleophile

Front 27

NH3

Back 27

weak nucleophile

Front 28

aprotic is needed in SN2 bc

how does H bond affect nu- in in protic during SN1

Back 28

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

Front 29

OH-

Back 29

strong nuceophile

Front 30

CN-

Back 30

strong nucleophlile

Front 31

NH2-

Back 31

strong nucleophile

Front 32

vinylic proton

Back 32

proton that is attach to the double bond

Front 33

alcohol and strong acid like H2SO4 lead to

Back 33

elimination

Front 34

strong base with
3, 2, 1, alklyl halide

Back 34

3- E1
2- E2
1- E2/Sn2

Front 35

weak base with
3, 2, 1, alklyl halide

Back 35

3-Sn1/E1 in protic
2-Sn2 in aprotic
1-Sn2