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Class 12 - Alcohols Phenols Ethers-1
Class 12 - Alcohols Phenols Ethers-1
unsymmetrical ethers.
(a) Alcohols:
The common name of an alcohol is derived
IUPAC
The smaller, shorter alkyl group becomes the alkoxy substituent. The
larger, longer alkyl group side becomes the alkane base name. Each
alkyl group on each side of the oxygen is numbered separately. The
numbering priority is given to the carbon closest to the oxgen. The
alkoxy side (shorter side) has an "-oxy" ending with its corresponding
alkyl group. For example, CH3CH2CH2CH2CH2-O-CH2CH2CH3 is 1-
propoxypentane. If there is cis or trans stereochemistry, the same rule
still applies.
In alcohols, the oxygen of the –OH group is
attached to carbon by a sigma (σ ) bond
formed by the overlap of a sp3 hybridised
orbital of carbon with a sp3 hybridised orbital
of oxygen.
The bond angle in alcohols is slightly less than
the tetrahedral angle (109°-28′). It is due to the
repulsion between the unshared electron pairs of
oxygen.
In phenols, the –OH group is attached to sp2
hybridised carbon of an aromatic ring.
The carbon– oxygen bond length (136 pm) in
phenol is slightly less than that in methanol. This
is due toof(i)the
account partial double bond
conjugation character
of unshared on ron
elect
2
pair of oxygen with the aromatic ring (ii) sp
hybridised state of carbon to which oxygen is
attached.
In ethers, the four electron pairs, i.e., the two
bond pairs and two lone pairs of electrons
on oxygen are arranged approximately in
atetrahedral arrangement.
The bond angle is slightly greater than the
tetrahedral angle due to the repulsive
interaction between the two bulky (–R)
groups.
The C–O bond length (141 pm) is almost the
same as in alcohols.
1. From alkenes
(i) By acid catalysed hydration:
R
Ethanol C2H5OH 46 +78 δ+
H
δ-
O Hydrogen bond
δ+ δ-
R
H
Propane C3 H 8 44 -42 O
R
Much higher b. pt
No. of hydroxyl grps present in the molecule
B. pt
Alcohol Formula Mr
/ oC b.p. of alcohols increase
with number of –
OH
Ethanol CH3CH2OH 46 +78 grps present
CH3CH2CH2CH2OH
Butan-1-ol
increase +118
more spherical
in
branching (CH3)2CHCH2OH
smaller surface area of 2-methylpropan-
of chain 1-ol +108
contact b/w molecules
R – OH vs H – OH
by steam distillation.
o-Nitrophenol is steam volatile due to
intramolecular hydrogen bonding while
p - nitrophenol is less volatile due to
intermolecular hydrogen bonding which
causes the association of molecules.
With concentrated nitric acid, phenol is
converted to 2,4,6-trinitrophenol.
The product is commonly known as picric
acid.
On treating phenol with bromine, different reaction
products are formed under different experimental
conditions.
(a) When the reaction is carried out in solvents of low
polarity such as CHCl3 or CS2 and at low
temperature, monobromophenols are formed.
The usual halogenation of benzene takes place in the
presence of a Lewis acid, such as FeBr3 which
polarises the halogen molecule.
In case of phenol, the polarisation of bromine
molecule takes place even in the absence of Lewis
acid.
It is due to the highly activating effect of –OH
group
attached to the benzene ring.
(b)When phenol is treated with bromine
water, 2,4,6-tribromophenol is formed as
white precipitate.
Phenoxide ion generated by treating phenol
with sodium hydroxide is even more reactive
than phenol towards electrophilic aromatic
substitution.
Hence, it undergoes electrophilic
substitution with carbon dioxide, a
weak electrophile.
Ortho hydroxybenzoic acid is formed as the
halide molecules.
Alkyl aryl ethers are cleaved at the alkyl-oxygen
bond due to the more stable aryl-oxygen
bond. The reaction yields phenol and alkyl
halide.