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Question 1

what is the stereospecificity of sn2 reactions

Answer 1

if the alpha carbon is chiral, during substitution, configuration switches
r turns to s (wedge switches to back)

Question 2

strong base, weak nucleophile results

Answer 2

E2

Question 3

strong base, strong nucleophile results

Answer 3

1: some E2, most SN2
2: most E2, some SN2
3: E2

Question 4

weak base, strong nucleophile results

Answer 4

1: SN2
2: SN2
3: SN1

Question 5

strong base, strong nucleophile solutions

Answer 5

NaOH, NaOCH3, CN, NaEtOH, NaOMe

Question 6

weak base, strong nucleophile solutions

Answer 6

NaBr, NaI, NaSH, NaCl

Question 7

what is the difference between zaitsev and hoffmann products

Answer 7

e2 products
zaitsev is more substituated, stable, common
hofmann is minor product unless bulky base used

Question 8

when do key players need to be in periplanar positions

Answer 8

E2 when B positions are chiral

Question 9

in cyclohexenes, the leaving group has to be ____ than the halide

Answer 9

OPPOSITE (one up, one down)

Question 10

why do alcohols need an acidic solution for reactions

Answer 10

OH is really unstable and needs to pair with another H to become H2O
OH does proton transfer to become H2O+, loss of leaving group, attack from nucleophile

Question 11

what are polar aprotic solutions

Answer 11

do not have H
best for SN2 because of no hydrogen bonding
nucleophiles free to react
acetone, DMF, DMSO

Question 12

what are polar protic solutions

Answer 12

contain H that bond with substrate
best for SN1 because they stabilize carbocation
H2O, ethanol, ammonia

Question 13

what is added in hydrohalogenation

Answer 13

H + X
markovnikov
racemic mixture (both syn and anti)
may do carbocation rearrangements

Question 14

what is added in hydration

Answer 14

H + OH
3 types

Question 15

what is added in hydogenation

Answer 15

H + H

Question 16

what is added in halogenation

Answer 16

X + X
anti (one wedge, one behind) bc backside attack
may have meso so watch out

Question 17

what is added in halohydrin

Answer 17

OH + X
bromonium ion (Br bridge intermediate) + H2O
anti additon

Question 18

what is added in dihydroxylation

Answer 18

OH + OH
anti addition: RCO3H, H3O
syn addition: OsO4/KMnO4, H2O

Question 19

markovnikov vs anti markovnikov

Answer 19

markovnikov: regiochemical preferences (Cl goes to more substituted spot rather than H)
anti is opposite

Question 20

what are racemic mixtures

Answer 20

the 2 enantiomers produced appear in equal amounts 50/50 that X is on wedge or behind

Question 21

why does it matter to do carbocation rearrangements

Answer 21

not the most stable molecule so it shifts
not a racemic mixture of results anymore, some will bond before shift happens

Question 22

what is acid catalyzed hydration

Answer 22

addition of H + OH across a double bond in presence of catalyst (acid (H, H2SO4, H30)
markovnikov
racemic mixture

Question 23

what happens in acid catalyzed reactions with dilute H2SO4 and more H20

Answer 23

addition

Question 24

what happens in acid catalyzed reactions with concentrated H2SO4 and less H20

Answer 24

elimination

Question 25

what is oxymercuration/demercuration

Answer 25

markovnikov addition of H + OH across an alkene without carbocation rearrangement
HgOAc

Question 26

what is hydroboration oxidation

Answer 26

H + OH in presence of BH3, THF
anti markovnikov
syn addition

Question 27

what is catalytic hydrogenation

Answer 27

H + H in with catalyst (Pt)
syn addition when applicable (2 chiral centers), sometimes no need to worry bc 0 or 1 chiral center

Question 28

what is ozonolysis

Answer 28

reactions that add across an alkene and cleave C=C bond