ch 12 - alcohol

Question 1

Aldehyde to primary alcohol

Answer 1

a) NaBH4, MeOH

b) H2
—————-
Pt, Pd, or Ni

c) 1) LiAIH4
- ————
2) H2O

Question 2

What are NaBH4 and LiAIH4 used as?

Answer 2

reducing agents

Question 3

Ketone to a secondary alcohol

Answer 3

a) NaBH4, MeOH

b) H2
—————-
Pt, Pd, or Ni

c) 1) LiAIH4
- ————
2) H2O

Question 4

carboxylic acid to primary alcohol

Answer 4

H2O

Question 5

R group, double bonded oxygen, and Ome group to a primary alcohol

Answer 5

H2O

Question 6

what is reduction?

Answer 6

reducing a molecule with an oxygen to a molecule with a hydroxide (OH) group

Question 7

what is a grindard reaction?

Answer 7

a reaction between an alkyl halide and magnesium = contain an R group, Mg, and a halogen

Question 8

How is a protection group formed?

Answer 8

R-OH —–> TMSCL ——> R - O - TMS
————
Et3N

Question 9

How is a protection group released?

Answer 9

R-OH —–> TBAF ——> R-OH

Question 10

what is oxidation?

Answer 10

deprotinating a hydroxyl group to form an oxygen double bonded to a carbon

Question 11

secondary alcohol to a ketone

Answer 11

H2SO4, H2O

Question 12

primary alcohol to carboxylic acid

Answer 12

H2SO4, H2O

Question 13

primary alcohol to an aldehyde

Answer 13

a) PCC, Ch2Cl2
b) DMP, CH2CL2

c) 1) DMSO, (CoCl2)
- ————————
2) Et2N

Question 14

phenol to benzoquinone

Answer 14

H2SO4, H2O

Question 15

Sn1 reaction with a tertiary alcohol

Answer 15

Hx + H2O

Question 16

SN2 reaction with a secondary alcohol and bromine

Answer 16

a) HBr

b) 1) TsCl, py
- ————-
2) NaBr

c) PBr3

Question 17

SN2 reaction with a secondary alcohol and chlorine

Answer 17

a) SoCl2
————
py

b) HCl
————-
ZnCl2

Question 18

E1 and E2 reactions to form an alkene

Answer 18

a) concentrated H2SO4
——————————–
heat

b) TsCl / py —–> NaOEt

Question 19

how do you form an alkoxide?

Answer 19

with a strong base like NaH, Na, Li, K

Question 20

How do you form an alcohol from an alkene that did not already have an oxygen present in the molecule?

Answer 20

addition reactions

Question 21

what addition reactions form alcohol from an alkene?

Answer 21

a) dilute H2SO4 (acid catalyzed hydration)

b) 1) HgSO4(oAc2), H2O
- ——————————- (oxy/deoxymercuration)
2) NaBHr

c) 1) BH3 * THF
- ——————— (hydroboration oxidation)
2) H2O2, NaOH

Question 22

what are the reagents for acid catalyzed hydration and when do you use it?

Answer 22

dilute H2SO4

use it when the reaction allows for carbocation rearrangements

Question 23

what are the reagents for oxy/deoxymercuration and when do you use it?

Answer 23

1) HgSO4(oAc2), H2O
- ——————————-
2) NaBHr

use when the reaction does not allow for carbocation rearrangements

Question 24

what are the reagents for hydroboration oxidation and when do you use it?

Answer 24

1) BH3 * THF
- ———————
2) H2O2, NaOH

use when the hydroxyl group is added anti-markovnikov

Question 25

what is a diol?

Answer 25

a molecule with two hydroxyl groups

Question 26

what reagents can you use to create diols?

Answer 26

a) NaBH4, MeOH b) H2 ---------------- Pt, Pd, or Ni c) 1) LiAIH4 - ------------ 2) H2O

Question 27

what reagents can you use to create a diol that did not have an oxygen present?

Answer 27

a) 1) RCO3H - ---------------- anti-dihydroxylation 2) H3O + b) 1) catalytic OsO4 - ------------------------- syn-dihydroxylation 2) NMO

Question 28

SN1 reactions occur with ____ alcohols

Answer 28

tertiary

Question 29

SN2 reactions occur with _____ alcohols

Answer 29

primary