NIB - Nomenclature, Isomerism, Bonding 92(I)1.(a)...

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Nomenclature, Isomerism, Bonding NIB/ALQ/P. 1 92(I)1.(a) There are several isomers of benzenedicarboxylic acid. (i) Draw the structures of all possible isomers of benzenedicarboxylic acid. (ii) One of these isomers is used to make terylene. Outline the reaction involved. (iii) On heating, one of the isomers gives a compound W , with formula C 8 H 4 O 3 . Give the structure of W . ( Hint : It is a dehydration. ) ( 5 marks ) (b) Compound X with formula C 10 H 14 is optically active. On treatment with potassium manganate(VII), X gives benzoic acid ( C 6 H 5 COOH ). Give the structure of X . ( 2 marks ) 93(I)3.(a) Consider the following compound, X : H C 2 H H C 5 H H C 8 C 9 C 10 O H O (i) Give the hybridization state of the carbon atom indicated by a , b and c . a __________ b __________ c __________ (ii) Suggest expected values for the bond angles α , β and γ . α __________ β __________ γ __________ (iii) Upon catalytic hydrogenation, one mole of X reacts with two moles of H 2 . Draw the structure of the product and give its systematic name.
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NIB - Nomenclature, Isomerism, Bonding 92(I)1.(a)...

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