Kimia Organik II

Pertemuan 2-3
Alcohols and Ethers
Prof. Dr. Adel Zamri, MS, DEA
Ihsan Ikhtiarudin, M.Si

DEPARTMENT OF CHEMISTRY
FACULTY OF MATHEMATICS AND NATURAL SCIENCES
UNIVERSITY OF RIAU
PEKANBARU
2015
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!
Common Name and IUPAC Name
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:
Solubility of Alcohol in Water
Methanol
Ethanol
Ethylene Glycol
Diethyl ether
Synthesis 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!
Oxymercuration-demercuration
Reaction Step:
Mechanism:
Write the mechanism of reaction below!
Hydroboration
Answer the question below!
Hydroxylation of alkene
Permanganate Hydroxylation
Syn-dihydroxylation

Reagents : KMnO4, -OH, or better:

O O
OsO4 is reduced to OsVI.
Os
VIII
O O
OH
1. OsO4

2. H2S, H2O OH
Cis-1,2-cyclohexanediol

Gives complementary stereochemistry to anti-

dihydroxylation
Mech.: O
C O VIII O C VI O H2O
Os Os
C C
O O O O
Six electron TS
Osmate ester
C OH HO O
VI Can be reoxidized by added
+ Os oxidant, therefore can be made
C OH catalytic in Os
HO O
Good because Os is expensive; OsO4, H2S are toxic.
-
O + CH3
Other oxidants: H2O2 ; Fe3+; and N
catalytic OsO4 O
Exercise
Anti Hydroxilation: via epoxidation
Learn this reaction!
Learn this reaction!
Learn this reaction!
Reaction of Alcohols and Ethers
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 SOCl2
Pyridine as solvent
Learn the mechanism!
Conversion of Alcohol to MsCl / TsCl
Displace hydroxy with halogen using
TsCl (Tosyl Clhoryde)
Learn the mechanism!
R H+ R X R
OH OH2 X

R PBr3
OH R
Br

R F3CSO2Cl X
OH R SO2CF3 R
O X

R Ts-Cl X R
OH R Ts
O X

R SOCl2 R
OH Cl + SO2 + HCl

O O
SOCl2
+ SO2 + HCl
R OH R Cl
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
Problem
Problem
Preparation of Ethers form Alcohols
The Williamson Ether Synthesis
Alcohols and Ethers from Epoxides
Reactions of Ethers with HCl/HBr
HBr excess condition:
 Examination

Nomenclature and Reaction

Nomenclature
Predict the Product of Reaction Below!

Learn The
Mechanism!
Oxidation and Reduction of Alcohols
Strong Oxidizing Agents
Jones Reagent : Strong Oxidizing Agent
Problem
Additional Methods for oxidizing Alcohol
Oxidation with KMnO4 and HNO3
Oxidation with CuO
Swern Oxidation
Problem
Solved Problem
Problem
Reduction of Alcohols
Problem
Mechanism
 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.