Mechanism Determination

Question 1

Strong nuc, weak base 1*

Answer 1

SN2

Question 2

Strong nuc, weak base 2*

Answer 2

SN2

Question 3

Strong nuc, weak base 3*

Answer 3

SN1

Question 4

Weak nuc, strong base 1*

Answer 4

E2

Question 5

Weak nuc, strong base 2*

Answer 5

E2

Question 6

Weak nuc, strong base 3*

Answer 6

E2

Question 7

Strong nuc, strong base 1*

Answer 7

E2 (minor) + SN2 (major)

Question 8

Strong nuc, strong base 2*

Answer 8

E2 (major) + SN2 (minor)

Question 9

Strong nuc, strong base 3*

Answer 9

E2

Question 10

Weak nuc, weak base 1*

Answer 10

SN2 + E2 (impractical?)

Question 11

Weak nuc, weak base 2*

Answer 11

All reactions (impractical)

Question 12

Weak nuc, weak base 3*

Answer 12

SN1 + E1

Question 13

NaOH

Answer 13

strong nuc, strong base

Question 14

NaOMe

Answer 14

strong nuc, strong base

Question 15

NaOEt

Answer 15

strong base, strong nuc

Question 16

H2SO4 + heat

Answer 16

E1

Question 17

H2O

Answer 17

weak nuc, weak base

Question 18

NaSH

Answer 18

strong nuc, weak base

Question 19

tBuOK - Potassium Tertbutoxide
(draw out)

Answer 19

E2 ONLY - sterically hindered so hofmann is major

Question 20

NaSMe

Answer 20

strong nuc, weak base

Question 21

LOA

Answer 21

E2

Question 22

MeOH

Answer 22

weak nuc, weak base

Question 23

How to determine if a weak or strong nuc:

Answer 23

If negative charge, then strong.
If no negative charge, then weak.

Question 24

How to determine a weak or strong base:

Answer 24

strong: negatively charged oxygens, less electronegative atoms
weak: neutral, high electronegative atoms (halides - Cl, Br, I), resonance stabilized

Question 25

LDA - Lithium Diisopropyl Amine
(draw out)

Answer 25

Elimination, E2
weak nuc, strong base

Question 26

NaH

Answer 26

weak nuc, strong base

Question 27

NaCN

Answer 27

strong nuc, weak base

Question 28

MeOH

Answer 28

weak nuc, weak base

Question 29

If weak nuc, weak base, and bad LG then

Answer 29

NR

Question 30

If neopentyl

Answer 30

NR