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A neutral compound (A) having C,H and O,...

A neutral compound (A) having C,H and O, on refluxing with HI yields methyl iodide and an alkyl iodide (B), which contains 74.6 per cent iodine. (B) when treated with moist `Ag_(2)O` produces a prodcut which undergoes the haloform reaction. Characterize (A), what would have been produced if (B) were treated with dry `Ag_(2)O` ?

Text Solution

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(i) As the compound [A] reacts with HI to from methyl iodide and alkyl iodide [B], it is methyl alkyl ether.
`R-underset([A])O-CH_(3)+2HIrarrCH_(3)-underset([B])I+R-I+H_(2)O`
(ii) Form the percentage of iodine `(74*6%)` , the molecular mass of [B] can be calculated as follows :
`" " R-I-=" "I`
`" " 100 g " " 74*6g`
`" " ? " " 127g`
If amount of iodine is `74*6`g, amount of R-I=100 g
If amount of iodine is 127 g, amount of `R-I=((100g))/((74*6g))xx(127g)=170`
Thus `" "` mass of alkyl group =170-127=43
`" "` The alkyl group is `=C_(3)H_(7)-`
(iii) As the compound [B] on reacting with moist silver oxide. (AgoH) gives an alcohol that undergoes haloform reaction, this clearly shows that the compound [B] is isopropyl iodide which gives isopropyl alcohol. Thus , the compound [A] is methyl isopropyl ether. The reactions involved are as follows :
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