Alcohol Reactions + Preperation

Question 1

What are the four ways to prepare Alcohols?

Answer 1

Substitution, Addition, Reduction of Carbonyl, Grignard Reactions

Question 2

What are the three additional reactions to prepare Alcohols?

Answer 2

Acid-Catalyzed Hydration, Oxymercuration-Demercuration, Hydroboration-Oxidation

Question 3

What are the reagents for Acid-Catalyzed Hydration?

Answer 3

H3O+ and H2SO4 as catalyst

Question 4

What are the reagents of Oxymercuration-Demercuration?

Answer 4

1. Hg(OAc)2, H2O
2. NaBH4

Question 5

What are the reagents of Hydroboration-Oxidation?

Answer 5

1. BH3 (dot) THF
2. H2O2, NaOH

Question 6

Is Hydroboration Markovnikov or Anti-Markovnikov?

Answer 6

Anti-Markovnikov

Question 7

Is Oxymercuration Markovnikov or Anti-Markovnikov?

Answer 7

Markovnikov

Question 8

Is Acid-Catalyzed Hydration Markovnikov or Anti-Markovnikov?

Answer 8

Markovnikov

Question 9

What are the three agents that can reduce Carbonyls?

Answer 9

1. H2 + Pt
2. NaBH4 + EtOH/NaOH or H2O
3. LiAlH4 + H2O

Question 10

What is the difference between Catalytic Hydrogenation from the other two reactants?

Answer 10

Catalytic Hydrogenation reduces the carbonyl and an alkene. NaBH4 and LiAlH4 only reduce the carbonyl.

Question 11

What’s the difference between NaBH4 and LiAlH4?

Answer 11

LiAlH4 (LAH) is strong enough to reduce esters and carboxylic acids *ONLY IF LAH IS IN EXCESS (requires two cycles of the mechanism to fully reduce these groups. NaBH4 is not strong enough. Both create primary alcohols.

Question 12

What is a Diol?

Answer 12

A compound with two hydroxyl groups. Glycol is synonymous with Diol.

Question 13

What are the two ways to prepare Diols?

Answer 13

1. Reduction of diketones (a compound with two ketones) using previously mentioned reducing agents)
2. Anti or Syn Dihydroxylations with an Alkene.

Question 14

What are Grignard Reagents?

Answer 14

CH3MgBr. These are alkyl halides treated with Mg. This allows carbon atoms to act as an anion. Allows for the addition of Carbon groups and stuff. **CAN ONLY REACT WITH ALDEHYDES, KETONES, ESTERS, EPOXIDES

Question 14

What is added alongside Grignard Reagents?

Answer 14

H2O so it doesn’t get destroyed.

Question 15

What are three ways to convert 1st and 2nd-degree alcohols to Alkyl Halides?

Answer 15

1. TsCL, py + NaBr
2. SOCl2, py
3. PBr3
   All three cause inversion of stereochemistry.

Question 16

How do you protect alcohol from Grignards?

Answer 16

The reagent is TMSCl and Et2N. TMS attaches to Oxygen.

Question 17

How you do remove TMS to bring it back to alcohol?

Answer 17

You use TBAF or H3O+

Question 18

What is the order of oxidation of Primary Alcohols?

Answer 18

Proceeds to an Aldehyde and then a Carboxylic Acid

Question 19

What is the order of oxidation of Secondary Alcohols?

Answer 19

Straight to Ketone

Question 20

What are the oxidizing agents of Alcohols?

Answer 20

Chromic acid for full oxidation. PCC can be used to bring primary alcohol to only an aldehyde

Question 21

What are the reagents for the oxidation of Alcohols for chromic acid?

Answer 21

1. Na2Cr2O7
2. H2SO4, H2O
   or
3. CrO3
4. H3O+, Acetone

Question 22

What are the reagents for the oxidation of Alcohols for PCC?

Answer 22

PCC
CH2Cl2 is solvent

Question 23

What are the alternative reagents for oxidation to create aldehydes from alcohols?

Answer 23

1. DMSO, (COCl)2
2. Et3N
   or
3. DMP
4. CH2Cl2