Derivatives of hydrocarbons

Alcohol and Ethers

Chapter 4.1
Derivatives of hydrocarbons
Alcohol
Chapter 3.2
 Alcohols
Alcohol structure and properties
Alcohol Nomenclature
Synthesis of Alcohol
Classification of Alcohol
Reactions of Alcohol
Phenols
 H
H C OH
H
 QUICK EXERCISE
Write the structural formulae of the
following compound

a) Naphthalen-2-ol

b) 3-phenyl-2-butanol

c) 2-phenylethanol
d) benzene-1,2,3-triol
Destructive Alcohol
hydrolysis of alkyl halide
reaction of grignard reagents
with aldehydes & ketones
reduction of aldehydes
& ketones
Hydrolysis of alkyl halide

RBr + NaOH ROH + NaBr

 Reaction of Aldehydes & Ketones

Reaction of grignard reagents with aldehydes &

ketones
R R

C 1. diethyl ether
R MgX + O R C OH
2. H3O+
Grignard R
R
reagent Aldehydes /
ketones
 Reaction of Aldehydes & Ketones

Reduction of aldehydes
R R
Pt
C O + H2 H C OH
ethanol
H H
1 alcohol
Reduction of ketones
R R
Pt
C O + H2 H C OH
ethanol
R' R'
2 alcohol
K2Cr2O7/H2SO4
 Reactions of alcohols
Dehydration
Removal of water to produce alkyl halide
R-OH + HX R-X + H2O
Hydrogen halide

Reaction with sodium

RO-H + Na RO Na+ + 1/2H2
Sodium alcoxide
Esterification
Produce an ester and water
O H2SO4 O
R-OH + RCOH heat RCOR + H2O
Carboxylic acid ester
Derivatives of hydrocarbons
Ether
Chapter 4.2
Alcohols
Ethers structure and properties
Ethers Nomenclature
Synthesis of Ethers
Reactions of Ethers
 Synthesis of ethers
Dehydrolysis of alcohol
acid-catalyzed reaction
referred as condensation
 H+
RCH2O + CH2R RCH2O CH2R + H OH
heat
H OH
Example:
H2SO4, 130C
+
favorable for primary alcohols
 2CH3CH2OH CH3CH2OCH2CH3 H2O ethanol
ethoxyethane

Synthesis of ethers

Williamson Synthesis
reflux
RONa + RX ROR + NaX
Sodium 1 alkyl halide ether Sodium alcoxide halide

Example:

CH3CH2ONa + CH3CH2Br CH3CH2OCH2CH3 + NaBr

Sodium ethoxide Bromoethane Ethoxyethane Sodium
bromide

Reaction of ethers

Combustion
highly flammable
can be exploded if the vapour mixed with air

C2H5OC2H5 + 6O2 4CO2 + 5H2O

Acid-catalyzed reaction
mixing ether with hydrogen halide and concentrated
acid
 H+
ROR + 2HX 2RX + H2O
heat