EXAM 2

Question 1

solvent Sn1/E1

Answer 1

polar protic, stabilize carbocation intermediate

Question 2

nucleophile Sn1

Answer 2

weak, non-basic

Question 3

nucleophile E1

Answer 3

basic

Question 4

nucleophile E1

Answer 4

strong, basic

Question 5

nucleophile SN2

Answer 5

strong, non-basic

Question 6

solvent Sn2, E2

Answer 6

polar aprotic

Question 7

primary sn1

Answer 7

no reaction

Question 8

secondary sn1

Answer 8

only if weak nucleophile or carbocation resonance stabalized

Question 9

tertiary sn1

Answer 9

favored with weak and non-basic nucleophiles

Question 10

primary e1

Answer 10

no reaction

Question 11

secondary e1

Answer 11

only if carbocation resonance stabalied

Question 12

tertiary e1

Answer 12

favored basic nucleo

Question 13

primary sn2

Answer 13

favored

Question 14

secondary sn2

Answer 14

only if strong, non-basic nucelophile

Question 15

tertiary sn2

Answer 15

no reaction

Question 16

primary e2

Answer 16

favored

Question 17

secondary e2

Answer 17

favored if strong base

Question 18

tertiary e2

Answer 18

only if strong base

Question 19

E2 solvent, nucleophile, control, rate depends on, prefer what substrate

Answer 19

polar aprotic, strong and basic, kinetic, substrate and base, primary

Question 20

E1 solvent, nucleophile, control, rate depends on, prefer what substrate

Answer 20

polar protic, weak and basic, thermodynamic, substrate, tertiary

Question 21

Sn1 solvent, nucleophile, control, rate depends on, prefer what substrate

Answer 21

polar protic, weak and non-basic, thermodynamic, tertiary

Question 22

Sn2 solvent, nucleophile, control, rate depends on, prefer what substrate

Answer 22

polar aprotic, strong and non-basic, kinetic, nucleophile and substrate, primary

Question 23

oxidation (o, e-, h)

Answer 23

gain of oxygen, loss of e-, loss h

Question 24

reductio (o, e-,h)

Answer 24

loss of o, gain of e-, gain h

Question 25

larger Rf

Answer 25

less polar since doesn't stick to stationary phase

Question 26

electrophilic addition of H-BR (# steps,intermediate, what's required, control, major product determined by

Answer 26

two steps, carbocation, strong acid required, kinetic, lowest energy carbocation

Question 27

electrophilic addition of H-BR (# steps, intermediate, what's required, control, major product determined by

Answer 27

two steps, cyclic ion, weaker nucleophile, carbon atom that can best stabilize portion of negative charge (more substituted/less H)