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Q.Write following chemical reactions with chemical equations:

(i) Reaction of phenols with sodium (acidic nature)
(ii) Reimer-Tiemann reaction. OR Write chemical equation for the following conversions:
(i) Propene to Propan-2-ol
(ii) Benzyl chloride to Benzyl alcohol
Madhya Pradesh MpbseMP Board Higher Secondary 2024Subjective· 3mImportance★★★★★
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Either two named phenol reactions, or two given conversions (attempt any one).

(i) Reaction of phenol with sodium (acidic nature):

Phenol is weakly acidic (its O-H hydrogen ionises because the phenoxide ion is resonance-stabilised by the benzene ring). It reacts with active metals like sodium, liberating hydrogen gas:

2 C6H5OH + 2 Na -> 2 C6H5ONa (sodium phenoxide) + H2 (gas)

Reimer-Tiemann reaction:

Phenol is treated with chloroform and aqueous NaOH at ~340 K; the dichlorocarbene generated in situ attacks the phenoxide ring (ortho to OH), and after hydrolysis this yields o-hydroxybenzaldehyde (salicylaldehyde) as the major product:

C6H5OH + CHCl3 + 3NaOH --(heat)--> o-HO-C6H4-CHO (salicylaldehyde) + 3NaCl + 2H2O

OR (ii) Given conversions:

Propene to propan-2-ol (Markovnikov addition of water, acid-catalysed hydration):

CH3-CH=CH2 + H2O --(dil. H2SO4)--> CH3-CH(OH)-CH3

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