Chemical properties of monohydric alcohols : Characteristic reaction of alcohol are the reaction of the - OH group. The reactions of the hydroxyl group consists of either cleavage of C - O bond or the cleavage of O - H bond.
C - O bond is weaker in the case of tertiary alcohols due to +I effect of alkyl groups while - OH bond is weaker in primary alcohols as electron density increase between O - H bond and hydrogen tends to separates as a proton.
Thus primary alcohols give the most of reaction by cleavage of O - H bond while tertiary alcohols are most reactive because of cleavage of C - O bond. Hence - O - H cleavage reactivity order : Primary > Secondary > Tertiary and C - O - cleavage reactivity order : Tertiary > Secondary > Primary alcohol
(i) Alkylation :
(ii) Reaction involving cleavage of with removal or substitution of -OH group
(a) Reaction with hydrogen halides : Alcohols give alkyl halide. The reactivity of HX is in the order of HI > HBr > HCl and the reactivity of ROH is in the order of benzyl > allyl > 3° > 2°> 1°. The reaction follows a nucleophilic substitution mechanism.
If alcohols react with HI and red phosphorus, alkane will be formed.
Primary alcohols follow S N2 mechanism .
In secondary and tertiary alcohols, the S N1 mechanism operates
(b) Reaction with PCl5 : (Analytical test for alcohols)
(c) Reaction with PCl3 :
(d) Reaction with thionyl chloride [SOCl2] :
(e) Reaction with ammonia :
(f) Reaction with HNO3 :
(g) Reaction with H2SO4 [Dehydration of alcohol] : The elimination of water from a compound is known as dehydration. The sequence of simple dehydration is Tertiary > Secondary > primary alcohol. The multiplication of dehydration of alcohols is depending upon the nature of dehydrating agents and temperature.
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