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RSAB - Reactivity Stability Acidity Basicity 90(II)9(a...

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Reactivity, Stability, Acidity, Basicity RSAB/ALQ&A /P.1 90(II)9.(a) Each of the following carbonyl compounds P , Q and R reacts with 2,4- dinitrophenylhydrazine in the presence of a strong acid to give a phenylhydrazone derivative. C CH 2 CH 2 CH 3 O C CH 2 CH 2 CH 3 O C O CH 2 CH CH 3 CH 3 CH 3 CH 3 CF 3 P Q R (ii) Under the same conditions, P, Q and R form phenylhydrazones at different rates. Predict with an explanation which react the fastest, and which the slowest. (iii) Explain why 2,4-dinitrophenylhydrazones are useful derivatives of carbonyl compounds. ( 7 marks ) 91(I)1.(b) (i) C H O C H CH 2 CH 3 CH 3 F E Explain why hydroxylamine reacts with F and not with E , and give the product expected from the reaction. ( 3 marks ) 92(II)9.(b) Arrange the following hydroxy-compounds in order of increasing acidity. Explain your order. OH OH NO 2 OH ( 5 marks )
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Reactivity, Stability, Acidity, Basicity RSAB/ALQ&A /P.2 93(I)3.(f) Consider the following compounds : C H OH O OH CH 3 and Y Z (i) Account for the fact that both Y and Z are acidic. (ii) Which compound, Y or Z , is the stronger acid ? Explain. ( 4 marks ) 95(I)3.(a) Arrange the following carbocations in the order of increasing stability. Explain your arrangement. CH 2 CH 2 , and + + + ( 3 marks ) (b) Arrange the following carboxylic acids in the order of increasing acidity. Explain your arrangement. ClCH 2 CO 2 H , ClCH 2 CH 2 CO 2 H and FCH 2 CO 2 H ( 3 marks ) 96(I)3.(a) Arrange the following carbocations in the order of increasing stability. Explain your arrangement. CH 3 CH 3 CH 2 and , + + + ( 3 marks ) (b) Arrange the following compounds in the order of increasing basic strength. Explain your arrangement. ( 3 marks )
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Reactivity, Stability, Acidity, Basicity RSAB/ALQ&A /P.3 NH 2 NH 2 NH 3 , and 99(II)4.(c) (i) Arrange, with explanation, the compounds below in the order of increasing acidity.
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