9701_s12_qp_21
A paper of Chemistry, 9701
Questions:
5
Year:
2012
Paper:
2
Variant:
1

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For Examiner’s Use Organic compounds which contain oxygen may contain alcohol, aldehyde, carboxylic acid, ester or ketone functional groups. The functional groups may be identifi ed by their reactions with specifi c reagents. Compound X has the empirical formula CH2O and Mr of 90. There is no reaction when X is treated with NaHCO3. What functional group does this test show to be not present in X? When 0.600 g of X is reacted with an excess of Na, 160 cm3 of H2, measured at room temperature and pressure, is produced. What functional group does this reaction show to be present in X? Use the data to calculate the amount, in moles, of hydrogen atoms produced from 0.600 g of X. Hence, show that each molecule of X contains two of the functional groups you have given in . For Examiner’s Use When X is warmed with Fehling’s reagent, a brick red precipitate is formed. Treatment of X with 2,4-dinitrophenylhydrazine reagent produces an orange solid. What functional group do these reactions show to be present in X? Draw the displayed formula of this functional group. Use your answers to , and to deduce the structural formula of X. What is the structural formula of the organic product of the reaction of X with Fehling’s reagent? Compound X can be both oxidised and reduced. Give the structural formula of the compound formed when X is reacted with NaBH4 under suitable conditions. Give the structural formula of the compound formed when X is heated under refl ux with acidifi ed K2Cr2O7.