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An oily liqid A is insoluble in water,but on heating with aq. soln. of NaOH for 1 hr. it dissolves.From the reaction mixture ,a liquid B can be distilled,which gives yellow ppt with NaOH/I2 as well as it is resolvable.B on treatment with acidic dichromate soln. yields C,which gives positive iodoform test.If sulfiric acid is added to soln obtained by heating with NaOH,a white ppt. D is obtained.D gives effervesence with NaHCO3 and on heating D with soda lime converts to toulene .Also A on treatment with Br2/FeCl3 in dark yields a single mono bromo derivative as a substitution product.B on heating with conc. H2SO4 gives stereomeric alkene,one of which on treatment with cold,dil,alk KMnO4 gives meso diol.Find structures of A to D
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10 Answers
1From the reaction mixture ,a liquid B can be distilled,which gives yellow ppt with NaOH/I2 as well as it is resolvable.
B on heating with conc. H2SO4 gives stereomeric alkene,one of which on treatment with cold,dil,alk KMnO4 gives meso diol
eureka the above two statements contradicting each other
first suggest 2-hydroxy propane
second suggest 2 hydroxy butane
1in this case the first statement will be non resolvable rather than resolvable