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Phenbol Reaction

1. Phenol undergoes Kolbe's reaction and Reimer-Tiemann reaction. Kolbe's reaction involves heating sodium phenoxide with carbon dioxide under pressure to produce salicylic acid. Reimer-Tiemann reaction involves reacting phenol with chloroform in the presence of sodium hydroxide to produce o-nitrophenol. 2. The -OH group of phenol activates the benzene ring towards electrophilic aromatic substitution by directing incoming groups to the ortho- and para-positions through resonance. This allows phenol to be converted to aspirin. 3. o-Nitrophenol is more volatile than p-nitrophenol because o-

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117 views3 pages

Phenbol Reaction

1. Phenol undergoes Kolbe's reaction and Reimer-Tiemann reaction. Kolbe's reaction involves heating sodium phenoxide with carbon dioxide under pressure to produce salicylic acid. Reimer-Tiemann reaction involves reacting phenol with chloroform in the presence of sodium hydroxide to produce o-nitrophenol. 2. The -OH group of phenol activates the benzene ring towards electrophilic aromatic substitution by directing incoming groups to the ortho- and para-positions through resonance. This allows phenol to be converted to aspirin. 3. o-Nitrophenol is more volatile than p-nitrophenol because o-

Uploaded by

ilias1973
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From :mohammed.

ilias

Named reaction

Phenol reaction
Kolbes Reaction
Sodium phenoxide
on
heating with co2 at 400K
under a pressure of 47atmospheres followed by
acidification gives salicylic
acid

Reimer-Tiemann
Reaction

Phenol
reacts
with
chloroform (CHCl3) in
presence of NaOH at
340K to form

Electrophilic Aromatic Substitution

of

phenol
The OH group activates the benzene ring
towards electrophilic substitution and directs
the incoming group to ortho- and parapositions due to resonance (+R effect), electron
density is more at ortho- and para- positions

Phenol to Asprin

From :mohammed.ilias

o-Nitrophenol is more volatile(or steam volatile) than p-nitrophenol

0- Nitrophenol exists as discrete molecules due to intramolecular Hbonding and hence is


more volatile than p- nitrophenol which exists as associated molecules due to
intermolecular H- bondng

Account for :(a) Alcohols have higher boiling points than that of hydrocarbons.
Alcohols form intermolecular H-bonding while hydrocarbons are
held together by weak van der waals forces.
(b) Propanol has higher boiling point than that of the hydrocarbon, butane.
Propanol forms intermolecular H-bonding but butane does not
(c) Alcohols are comparatively more soluble in water than hydrocarbons of
comparable moleculer masses.
Alcohols form H-bonding with water but hydrocarbons do not.
(c) Ethanol has higher boiling point than methoxymethane
Ethanol forms intermolecular H-bond but methoxymethane does not
(d) Phenols are more acidic than alcohols .
Phenoxide ion is resonance stabilized but alkoxide ion does not
(e) Cresols are less acidic than phenols.
Cresol is methyl phenol ( o -, m- or p-cresol). Due to +I-effect of CH3 group
makes less stable phenoxide ion and cleavage of O H bond becomes difficult
as electron density in O-H bond increases. So release of H+ ion becomes
difficultas compared to phenol.

(f) Ortho-nitrophenol is more acidic than orthomethoxyphenol


In o- nitrophenol, due to strong R and I-effect of the NO2 group,
electron density in O-H bond decreases and hence the loss of proton becomes
easy and phenoxide ion formed stabilised. white in o-methoxyphenol due to +R
effect of the OCH3 group , the election density in the OH bond increases and
increases and hence loss of proton becomes difficult and makes less stable
phenoxde ion.
(g) OH group attached to a carbon of benzene ring activates it towards
elcectrophilic substitution .
Due to +R effect of the OH group, the electron density in the benzene ring
and hence activates it towards electrophilic substitution at ortho and para
positions.
(h).unlike phenols , alcohols are easily protonated Or Alcohols are easily protonated
than phenols. Or Phenols do not give protonated reactions readily.
In phenols lone pair of electrons on the oxygen atom are delocalized due
toresonance and are not easily available for protonation. In alcohols lone pair of
electrons are localized due to absence of resonanace are easily available for
protonation .

From :mohammed.ilias

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