Alcohols: Reactions

CH21 PS class

Review your past reactions!

Review your past reactions!

Review your past reactions!

Review your past reactions!

Review your past reactions!

Other ways to synthesize R-OH

Other ways to synthesize R-OH

More reduction…

More reduction…

NaBH4/H3O+ does not really work for esters/ carboxylic acids.

Use LiAlH4 /H3O+ instead.

Practice!

Practice!

Practice!

Practice!

Grignard Reagents + carbonyls

Grignard Reagents + carbonyls

Grignard Reagents + carbonyls

Grignard Reagents + carbonyls

Grignard Reagents + carbonyls

Grignard Reagents + carbonyls

Practice!

Practice

Challenge: USE AN ESTER

Practice

Challenge: USE AN ESTER

Reactions of alcohols: Review SN1/2 E1/E2

Oxidation of R-OH

Acid-dehydration = E1

POCl3 in Pyridine

Practice

Practice

Practice

Practice

Practice

Practice

Oxidation of R-OH

Esters, overview

Oxidation of R-OH

Periodinane is also a viable reagent!

Oxidation of R-OH

Chromate mechanism

Practice

Practice

Practice

More Problems

ProblemsPropose a synthetic route from 2-phenylethanol to make:

AB C D

E

ProblemsPropose a synthetic route from 2-phenylethanol to make:

H2SO4 Pe

riodi

nane

CrO3

KMnO4

1. H2SO4 2. H2/Pd

Problems

Problems

ProblemsGive all Grignard Reagent + Carbonyl pairs to give the ff. alcohols:

A

B

C

D

Problems

A

B

ProblemsGive all Grignard Reagent + Carbonyl pairs to give the ff. alcohols:

A

B

C

D

Problems

C

D

Problems

Problems

Problems

Problems

ProblemsPROPOSE REAGENTS FOR EACH STEP.

ProblemsNaBH4, H3O+

PBr3

1. Convert to Grignard (Mg/ether)

2. add CH2=O then acid

1. Ph-CH2-MgBr 2. 2. H3O+

Periodinane

POCl3 or conc’d H2SO4