Alcohols and

Prof. Dr.Ethers
Adel Zamri, MS, DEA

DEPARTMENT OF CHEMISTRY
FACULTY OF MATHEMATICS AND NATURAL SCIENCES
UNIVERSITY OF RIAU
PEKANBARU
2013

Introduction

Alcohols

Ethers

Medicinal Research

Anesthetic

Nomenclature

Nomenclature of Alcohol:

To learning the others nomenclature of

alcohol, please watch the video of
nomenclature that have been given and use
the ChemDraw Software to help you!

Nomenclature of Ethers:

To learning the others nomenclature of

ethers, please watch the video of
nomenclature that have been given and use
the ChemDraw Software to help you!

Physical Properties

Physical Properties of Alcohol and

Ether:

Methanol

Ethanol

Ethylene Glycol

Diethyl ether

Reactions of Alcohols
and Ethers

Review SN2 Reaction...

Preparation of Alcohol

From Alkene: Acid Hydration

In aquaeus acid solution:

Why not like this?

Write the mechanism of reaction

below!

Hydroxylation of alkene

Mechanism:

Oxymercurationdemercuration

Reaction Step:

Mechanism:

Write the mechanism of reaction

below!

Hydroboration

Answer the question below!

Syn-dihydroxylation
Reagents : KMnO4, -OH, or better:
OsO4
reduced to OsVI.

is

Os
O

VIII

O
OH

1. OsO4
2. H2S, H2O

OH

Cis-1,2cyclohexanediol

Gives complementary
stereochemistry to antidihydroxylation

Mech.:

C
C

VIII

Os
O

Six electron TS

OH

OH

HO

VI

Os
O

H2O

Osmate ester
VI

Os
HO

Can be reoxidized by
added oxidant, therefore
can be made catalytic in
Os

Good because Os is expensive; OsO4, H2S are toxic.

O + CH3
Other oxidants: H2O2 ; Fe3+; N
and catalytic OsO4
O

Permanganate Hydroxylation

Exercise

Anti Hydroxilation

Learn this reaction!

Learn this reaction!

Learn this reaction!

Reactions from Alcohol

Displace hydroxy with halogen

using TsCl (Tosyl Clhoryde)

Conversion of alcohols to alkyl

halides

Mechanism:

How about Primary Alcohols and

methanol?

Predict the product and write the

mechanism!

Other ways to displace hydroxy

with halogen : using PBr3

Other ways to displace hydroxy

with halogen : using SOCl 2

Pyridine as solvent

Learn the mechanism!

Learn the mechanism!

R

OH

OH

OH

OH

OH
O

H+

PBr3

F3CSO2Cl

Ts-Cl
SOCl2

Br

SO2CF3
X

Ts

Cl

SO2

Cl

SO2

X
HCl

SOCl2
OH

OH2

HCl

Other way to displace hydroxy

with halogen: using ZnCl2

Starting with alcohol, outline a

synthesis of each of the following:
a. Benzyl bromide
b. Cyclohexyl chloride
c. butyl bromide

Dehydration of Alcohol:
Synthesis Alkene

Dehydration with
rearangement

Preparation of Ethers

The Williamson Ether

Synthesis

Solvomercurationdemercuration

Alcohols and Ether from

Epoxide

Reactions from Ethers

HBr excess condition:

Examination
Nomenclature, substitution and elimination of alcohols

Nomenclature

Reaction and Synthesis

Predict the product of reaction

below!

Predict the product of reaction

below!

Predict the product of reaction

below!

Oxidation and Reduction of

Alcohols

Problem

Problem

Additional Methods for oxidizing

Alcohol

Oxidation with KMnO4

and HNO3

Oxidation with CuO

Swern Oxidation

Problem

Solved Problem

Problem

Reduction of Alcohols

Problem

Cyclization and Rearangment of

Alcohol

Problem

Problem

Mechanism

Problem

Problem

Problem

References:
Bruice, P. Y. Organic Chemistry, 4th Ed.
Solomons, T. W. G. And Fryhle, C. B. 2011. Organic
Chemistry, 10th Ed. John Wiley and Sons, Inc.
Solomons, T. W. G. Fundamental of Organic
Chemistry.
Wade, L.G. 2006. Organic Chemistry, 6th Ed. Peason
Education, Inc., New Jersey.