C10: Alcohol Synthesis

Question 1

Phenol to phenoxide (2 different reagents)

Answer 1

NaOH

KOH

Question 2

Salts are produced when you combine a weak base with

Answer 2

carboxylic acid

NOT simple phenols or alcohols

Question 3

How to produce Gringard reagents

Answer 3

alkyl halide + Mg metal in ether solvent

Question 4

Alcohol synthesis from alkene (Markovnikov)

Answer 4

1. acid catalyzed hydration (rearrangement)
   _ + H20, (H+acid) = _
2. oxymercuration-demercuration (no rearrangement)
   _ + [1] Hg(OAc)2, H20 [2] NaBH4

Question 5

Markovnikovs Rule

Answer 5

Adds to the most substituted carbon

Question 6

Alcohol synthesis from alkene (Anti-Markovnikov)

Answer 6

1.hydroboration-oxidation

[1] _ + BH3.THF [2]H2O2 NaOH

Question 7

1,2 Diols from alkene (SYN)

Answer 7

_ + OsO4, H2O2 = _

_ + KMnO4, -OH, (cold dilute) = _

Question 8

1,2 Diols from alkene (ANTI)

Answer 8

[1 form epoxide] [2 Hydrate epoxide]

_ + [1] RCO3H, [2] H30+ =

Question 9

alkoxide from aceylide

Answer 9

_ + ketone/or/aldehyde = _

Question 10

acetylenic alcohol from alkoxide

Answer 10

_ + H30+ = _

Question 11

Gringard reagents require what two steps to complete reactions to alcohols

Answer 11

[1] ether solvent

[2] H30+

Question 12

Gringard + formaldehyde = ???

Answer 12

Primary alcohol

Question 13

Gringard + aldehyde = ???

Answer 13

Secondary alcohol

Question 14

Gringard + ketone = ???

Answer 14

Tertiary alcohol

Question 15

2 Gringard + ester = ???

Answer 15

Tertiary alcohol, cannot stop at ketone intermediate (2 groups added)

Question 16

2 Gringard + Cl-(R)-C=O acid chloride = ???

Answer 16

Tertiary alcohol, ketone

Question 17

Gringard + epoxide = ???

Answer 17

Primary alcohol (2 groups added)

Question 18

aldehyde + NaBH4 = ???

aldehyde + LiAlH4 = ???

Answer 18

Primary alcohol
R-CH2-OH
R-CH2-OH

Question 19

ketone + NaBH4 = ???

ketone + LiAlH4 = ???

Answer 19

Secondary alcohol
R-CH(OH)-R’
R-CH(OH)-R’

Question 20

alkene + NaBH4 = ???

alkene + LiAlH4 = ???

Answer 20

No Rxn

No Rxn

Question 21

acid anion, (anion in base) + NaBH4 = ???

acid anion, (anion in base) + LiAlH4 = ???

Answer 21

No Rxn

Primary R-CH2-OH

Question 22

ester + NaBH4 = ???

ester + LiAlH4 = ???

Answer 22

No Rxn

Primary R-CH2-OH

Question 23

Industrial Synthesis of Ethanol

Answer 23

Ethelene + H20 –high pressure, heat, P2O5 catalyst –> ____

Question 24

ethylene + O2/Hg+ = ???

Answer 24

epoxide/oirane

Question 25

the ______ hindered carbon of a strained ring is attacked, making ____ react faster than ____

Answer 25

least
primary
secondary

Question 26

H2C=CH-CH2-CH2-C(=O)-H —–> H3C-CH-CH2-CH2-C(OH)-H

reduce both C=O and C=C

Answer 26

H2 + Pd ( or Pt or Ni) Catalyst

Question 27

H2C=CH-CH2-CH2-C(=O)-H —–> H2C=CH-CH2-CH2-C(OH)-H

reduce only C=O

Answer 27

[1] NaBH4 or LiAlH4

[2] H20, H+

Question 28

ketone & ester compound + NaBH4 = ???

ketone & ester compound + LiAlH4 = ???

Answer 28

reduced OH of ketone, ester is unchanged

reduced OH of ketone, reduced OH of ester

Question 29

Aldehydes to Primary Alcohols

Answer 29

H2, Pd (or Pt or Ni) Catalyst

Question 30

Ketones to Secondary Alcohols

Answer 30

H2, Pd (or PT or Ni) Catalyst

Question 31

S-H bonds are ____ than O-H bonds therefore easily _____

Answer 31

weaker

oxidized

Question 32

Another name for Thiols

Answer 32

Mercaptans, capture mercury

Question 33

Na-S-H + R-X =???

Answer 33

_ + _ = R-SH + Na-X

Question 34

2 _____ –Br2, Zn, HCl–> ________ + 2HBr

Answer 34

_R-SH –__________–> R-S-S-R + ____

Question 35

Thiol —- KMnO4—> ???

Thiol —- HNO3 —> ???

Answer 35

expanded octet (R-(O=)S(=O)-O-H), charge separation (R-(O-)S(-O)-OH) or both (R-(O=)S(-O)-O-H)