STRUDET - Structural determination Sd/ALQ&A/P.1 90(II)7....

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Structural determination 90(II)7. Consider the following experimental information. I X ( C 9 H 11 NO ) gives on hydrolysis, two compounds with formulae CH 5 N and C 8 H 8 O 2 . When the latter compound is added to sodium hydrogencarbonate solution, a colourless gas is evolved. II Y ( C 9 H 10 ) gives on vigorous oxidation, an acid with formula C 7 H 6 O 2 . Y decolourizes a solution of bromine in tetrachloromethane. III Z is an optically active ester containing 64.6% carbon, 10.8% hydrogen, and 24.6% oxygen, and has a relative molecular mass between 120 and 140. Upon hydrolysis, Z gives propanoic acid. (a) Draw TWO possible structures for each of the compounds X , Y , and Z . (b) For each pair of possible structures, name the type of isomerism involved. (c) Using only one of the possible structures for each of X , Y , and Z , write equations for the reaction described above. ( Relative atomic masses : H, 1.0; C, 12.0; O, 16.0 ) ( 17 marks ) 91(II)9.(b) Suggest a possible structure for each of the compounds J , K , L , M and N below and explain briefly your deductions. (i) J , C 4 H 6 O, on oxidation gives K , C 4 H 6 O 2 . (ii) L , C 5 H 12 O , can exist as a pair of enantiomers, and reacts with phosphorus pentachloride to give hydrogen chloride. (iii) M , C 6 H 10 , on ozonolysis gives N , C 6 H 10 O 2 . ( 9 marks ) 93(II)9.(a) A compound W of relative molecular mass 121 has the elemental composition : C, 79.3%; H, 9.1%; N, 11.6%. W reacts with nitric(III) acid to give a derivative X . X reacts with ethanoic anhydride to give a sweet-smelling liquid Y which contains no nitrogen. Oxidation of X with chromic(VI) acid yields Z , C 8 H 8 O . Z reacts with iodine and sodium hydroxide to produce a yellow precipitate and sodium benzoate. 93(II)9.(a)
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Structural determination (i) Deduce the structures of W , X , Y and Z , using all the given data. Explain your reasoning. ( 10 marks ) (ii) Compound W is a liquid. Suggest, giving reason(s), a suitable derivative to characterise W . ( 2 marks ) 94(II)7.(b) Give, with explanation, THREE possible structures for each of the compounds ( G , H and J ) below. (i) G is a sweet smelling liquid which contains 54.4% carbon, 9.2% hydrogen, and 36.4% oxygen and has a relative molecular mass between 80 and 100. (ii) H , C 5 H 9 Cl , is an acyclic chloroalkene which is optically active. (iii) J , C 10 H 14 O , reacts with PCl 5 to give hydrogen chloride. Vigorous oxidation of J gives benzene-1,2-dicarboxylic acid, but mild oxidation of J gives a ketone. Suggest one chemical test, giving the expected observations, which would allow you to eliminate one of your possible structures of J in (iii). ( 14 marks ) 95(II)7.(b) An acidic compound D , C 4 H 4 O 4 , on heating to 140 ° C dehydrates to give compound E , C 4 H 2 O 3 . D gives compound F upon hydrogenation. (i)
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This note was uploaded on 08/17/2011 for the course CHEM 100 taught by Professor Fleet during the Fall '08 term at Oxford University.

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STRUDET - Structural determination Sd/ALQ&A/P.1 90(II)7....

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