Answer to Question #242566 in Organic Chemistry for Bong

Question

A compound A C5H12O when treated with 20% conc H2SO4 at 170Celcius yields compound B C5H10 which on ozonolysis yields two compounds C (C2H4O) and D (C3H6O).Compound A when treated with Lucas reagent turns cloudy immediately while compound B decolourizez both baeyer’s reagent and bromine water.Both compound C and D gave positive test with fehlings solution.Deduse the structure of A,B,C and D give their IUPAC names.

b)By use of chemical equation,show how you can synthesis Butyne from 2-Butane.

Answer 1

Organic compound A is an ester as on acid hydrolysis it gives a mixture of an acid and an alcohol.

Oxidation of alcohol (C) gives acid (B). Hence, the number of carbon atoms in (B) and (C) are same.

Ester (compound A) has eight C atoms. Hence, both carboxylic acid B and alcohol C must contain 4 C atoms each.

Dehydration of alcohol C gives but-1-ene. Hence, C must be a straight chain alcohol, i.e butan-1-ol.