question_answer 26)

An organic compound contains 69.77% carbon, 11.63%hydrogen and rest oxygen. The molecular mass of the compound is 86. Itdoes not reduce Tollen's reagent but forms an addition compound withsodium hydrogen sulphite and give positive iodoform test. On vigorousoxidation it gives ethanoic and propanoic acid. Write the possiblestructure of the compound. (i) Derive empiricsl and molecular formula by first finding moles. (ii) According to the given chemical reactions, derive the structuralformula. (iii) Write all the related equations.  

Answer:

Step I: To determine the molecular formula of thecompound.  

Element	Percentage	Atomic mass	No. of moles	Simplest molar ratio
C   H   O	69.77   11.63   (100-69.77-11.63) = 18.60	12   1   16

  Empirical formula of the given organic compound . Molecular formula = n x (empirical formula) where, Given, molecular mass = 86 Empirical formula mass of                                                            Molecular formula Step II: Predicting the structure of the compound. Criteria: 1. Formation of addition compound with  depictsthe presence of aldehyde or ketone. 2. The given compound does not reduce Tollen's reagent but givespositive iodoform test, so it is a methyl ketone. 3. On oxidation, the compound forms a mixture of ethanoic andpropanoic acid, so it is Step III: Chemical equations: 1.                 2. 3.