Consider the following compounds.
(i) 1-methoxy butane
(ii) 1-methoxy-2-methylpropane
(iii) 2-methoxy-2-methylpropane
(iv) Methoxybenzene
(v) Di-tert-butyl ether
How many of them yields methanol as one of the products on reaction with cold hydroiodic acid?
Text Solution
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Among the given compounds, only one, i.e. (iii) will give methanol as one of the products on
reaction with cold hydroiodic acid.
According to Zeisel method, when an ether reacts with cold HI, alkyl iodide and alcohol are formed. In case of unsymmetrical ether, the alkyl halide is always formed from the smaller alkyl group provided no tertiary ( 
) alkyl group is present and if any 
alkyl group is present, the halogen gets attached with it.
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