Requirements for each reaction

Question 1

SN1 steps

Answer 1

LG, NA (other steps can take place too)

Question 2

SN2 steps

Answer 2

H+ transfer, NA, H+ transfer

Question 3

Weak nucleophiles

Answer 3

F-, H2O, ROH

Question 4

Strong nucleophiles

Answer 4

I-, Br-, Cl-, HS-, H2S, RSH, HO-, RO, NC, H3O+

Question 5

SN2 uses _____ nucleophiles

Answer 5

Strong

Question 6

Inversion- ______ process

Answer 6

SN2

Question 7

SN1 products

Answer 7

Enantiomers

Question 8

(MOST IMPORTANT FACTOR) Less sub e-phile favors

Answer 8

SN2

Question 9

(MOST IMPORTANT FACTOR) More sub e-phile favors

Answer 9

SN1

Question 10

Strong nucleophile points to

Answer 10

SN2

Question 11

Good LGs are critical for both, but especially for

Answer 11

SN1

Question 12

Less than 7 membered ring can only be

Answer 12

cis

Question 13

Bredt’s rule

Answer 13

You can’t have a double bond at a bridgeheaded carbon in a ring with less than 8 members (spine of book)

Question 14

How do you know if an alkene is E or Z

Answer 14

Look at either side of 2x bond

Question 15

Is trans or cis more stable?

Answer 15

Trans

Question 16

E2 mechanism

Answer 16

Base attacks H, causing proton transfer. Then LLG, making alkene and LG-

Question 17

Rate of elimination rxn __________ with subs

Answer 17

Increases

Question 18

Hoffman product

Answer 18

Less stable

Question 19

Zaitsev product

Answer 19

More stable

Question 20

E1 mechanism

Answer 20

LLG, Base attacks H creating double bond erasing + charge

Question 21

E1 prefers Zaitsev (more sub) or hoffman (less sub)

Answer 21

Zaitsev

Question 22

More polarizable nucleophiles are

Answer 22

More effective

Question 23

Strong bases

Answer 23

H, DBN, DBU

Question 24

Strong nuc/strong base

Answer 24

OH, MeO, EtO

Question 25

Weak nuc, weak base

Answer 25

H2O, MeOH, EtOH

Question 26

Nucleophile only, 1 or 2 sub

Answer 26

SN2

Question 27

Nucleophile only, 2 or 3 sub

Answer 27

SN1

Question 28

Base only

Answer 28

E2

Question 29

strong base and strong nuc

Answer 29

E2 (Major for 2)

Question 30

strong base and strong nuc, 1 and 2

Answer 30

E2 (major for 1)

Question 31

Weak nuc, weak base, 1

Answer 31

SN2, E2 (slow)

Question 32

Weak nuc, weak base, 2

Answer 32

SN2, SN1 (slow), E2, E1

Question 33

Weak nuc, weak base, 3

Answer 33

SN1, E1