Alcohols and Phenols (Chapter 17)

Question 1

Things that alcohols can react with as acids

Answer 1

alkali metals, strong bases (NaH), NaNH2, Grignard Reagents

Question 2

Ways to make alcohols

Answer 2

Hydration of alkenes (hydroboration or hydroxymercuration)

Question 3

Ways to make 1,2 diols

Answer 3

1) OsO4/Pyridine, NaHSO3/H20

2) epoxide, H3O+

Question 4

Alcohols from Reduction (2 reagents, mechanism)

Answer 4

NaBH4, LiAlH4

Question 5

Alcohols from Reduction (4 types)

Answer 5

carboxylic acid - primary
ester - primary
aldehyde - primary
ketone - secondary

Question 6

Alcohols from Grignard Reaction (4 types, mech)

Answer 6

formaldehyde - primary
aldehyde - secondary
ketone - tertiary
ester - tertiary (adds some group twice?)

RMgX/ether,H30+

Question 7

Times when Grignard Reaction does not work for making alcohols

Answer 7

FG = -OH,-NH,-SH,-CO2H
FG = C=O(H,R,NR2), -C=-N,-NO2,-SO2R

Question 8

Alcohol + HCl/HBr mechanism

Answer 8

-

Question 9

Alcohol + SOCl2/PBr3

Answer 9

-

Question 10

Alcohol + tosylate + RO-

Answer 10

-

Question 11

Alcohol + SOCl2/PBr3 + RONa

Answer 11

-

Question 12

Acid Catalyzed Dehydration (+ cases used)

Answer 12

mostly tert, second only under extreme, E1

Question 13

Dehydration by reaction with…P… (+ cases used)

Answer 13

tert/sec, E2

Question 14

Conversion of alcohols into esters

Answer 14

ROH,HCl/heat

SOCl2,ROH

Question 15

oxidation of primary, secondary, and tertiary alcohols (results)

Answer 15

prim - aldehyde or carboxylic acid
sec - ketone
tert - no reaction

Question 16

Making aldehydes and carboxylic acids

show mech

Answer 16

Aldehydes - Dess-Martin periodinane

Carboxylic acids - most other common oxidizing reagents (CrO3)

Question 17

Making ketons

Answer 17

if tricky - Dess-Marin

if not, large scale - Na2Cr2O7