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INTRODUCTION
Hydroxy compounds include aliphatic alcohols,
IUPAC Nomenclature
Find the longest carbon chain containing
Name these:
CH3
CH3
CH CH2OH
2-methyl-1-propanol
OH
CH3
CH CH2CH3
2-butanol
CH3
CH3
OH
C OH
CH3
2-methyl-2-propanol
Br
CH3
3-bromo-3-methylcyclohexanol
=>
Classification
Primary: carbon with OH is bonded to one other carbon.
Secondary: carbon with OH is bonded to two other
carbons.
Tertiary: carbon with OH is bonded to three other
carbons.
Aromatic (phenol): -OH is bonded to a benzene ring.
H
CH 3
CH 3
CH3-C-OH CH3-C-OH CH3-C-OH
H
H
CH 3
Ethanol
2-propanol
2-methyl-2propanol
Primary (1o)
secondary (2o)
tertiary (3o)
alcohol
alcohol
alcohol
Physical Properties
Alcohols are polar compounds
H
O
H
C
H
Physical Properties
Hydrogen bonding:
bonding when the positive end
approximately 21 kJ (5 kcal)/mol
hydrogen bonds are considerably weaker
than covalent bonds
nonetheless, they can have a significant
effect on physical properties
Hydrogen Bonding
Physical Properties
In relation to alkanes of comparable size
REACTIONS
Formation of halogenoalkanes
Reactions with sodium
Oxidation
Dehydration
Esterification
Formation of
Halogenoalkanes
Reagent: Hydrogen halide (HX) or phosphorus
halide (PX3 or PX5) or SOCl2
1.With hydrogen halide
- the alcohol is refluxed with NaX and
concentrated H2SO4 (to produce HX)
- eg: NaCl + H2SO4
HCl + NaHSO4
C2H5OH + HCl
C2H5Cl + H2O
- most suitable for chlorides and bromides
-
gas
Eg: C2H5OH + Na
C2H5O-Na+ + 1/2H2
sodium ethoxide
Oxidation
Reagent : acidified K2Cr2O7 ( or acidified KMnO4)
Condition: heat or reflux
Observation: orange aq. K2Cr2O7 turns green ( due to
Secondary alcohols
- Are oxidised to ketones
Eg:
H
Cr2O72-/H+
CH3-C-CH3 + [O]
CH3C=O + H2O
OH
reflux
CH3
propanone
Tertiary alcohols
- are not oxidised
- Bcoz tertiary alcohols do no have any hydrogen
atom to be removed from the carbon atom to which
the OH group is attached
Thus, oxidation is used to distinguish primary,
secondary, and tertiary alcohols.
Dehydration
Reagent: excess concentrated H2SO4
Condition: heat at about 170oC
Product: alkenes
excess c. H2SO4
Eg: CH3CH2OH
CH 2=CH2 + H2O
ethanol
heat at 170oC
ethene
If excess ethanol is used & the temperature is
kept about 140oC, ether is produced instead
of ethene
c. H2SO4
2CH3CH2OH
ethanol (excess)
CH3CH2OCH2CH3 + H2O
heat at 140oC
ethoxyethane (ether)
Esterification
Reagent: carboxylic acid or acyl halide
Product: sweet-smelling ester
1. With carboxylic acid
- condition: reflux in the presence of a small amount of
concentrated H2SO4
Eg: CH3CH2O + CH3C=O
H
OH
ethanol
ethanoic acid
CH 3C=O
+ H 2O
OCH 2CH3
ethyl ethanoate
ethanoyl chloride
ethyl ethanoate
Identification tests to
distinguish classes of alcohols
1.
Lucas reagent
secondary
solution turns cloudy immediately
2.