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Q.Distinguish primary, secondary and tertiary alcohols on the basis of dehydrogenation products.

(OR)
Write chemical equations for the following conversions -
(a) Benzene from Phenol
(b) Ethanol from Sugarcane
(c) Ether from Ethanol
Uttarakhand UbseUttarakhand Board Intermediate (Class 12) 2024Subjective· 3mImportance★★★★★
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Passing alcohol vapours over hot Cu distinguishes 1°, 2°, 3° alcohols by the class of product formed.

When the vapours of an alcohol are passed over heated copper catalyst at about 573 K, the class of alcohol determines the product formed:

Primary alcohols (RCH2OHRCH_2OH) are dehydrogenated to aldehydes:

CH3CH2OH→Cu, 573KCH3CHO+H2CH_3CH_2OH \xrightarrow{Cu,\,573K} CH_3CHO + H_2

Secondary alcohols (R2CHOHR_2CHOH) are dehydrogenated to ketones:

(CH3)2CHOH→Cu, 573KCH3COCH3+H2(CH_3)_2CHOH \xrightarrow{Cu,\,573K} CH_3COCH_3 + H_2

Tertiary alcohols (R3COHR_3COH) have no hydrogen atom on the carbinol (C–OH) carbon itself, so they cannot be dehydrogenated to a carbonyl compound; instead they undergo dehydration over hot copper to give an alkene:

(CH3)3C−OH→Cu, 573K(CH3)2C=CH2+H2O(CH_3)_3C{-}OH \xrightarrow{Cu,\,573K} (CH_3)_2C{=}CH_2 + H_2O

Since the three classes give three chemically distinct product types (aldehyde / ketone / alkene, easily distinguished e.g. by Tollens'/Fehling's test), this dehydrogenation behaviour is used to distinguish primary, secondary and tertiary alcohols.

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