9701_w05_qp_2
A paper of Chemistry, 9701
Questions:
5
Year:
2005
Paper:
2
Variant:
0

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Compound Z, an organic compound with three functional groups, has the molecular formula C4H6O2. The functional groups can be confirmed by the following tests. Test for the first functional group. Z decolourises aqueous bromine. What functional group is shown to be present in Z by this test? Tests for the second functional group. Z reacts with sodium to give hydrogen and a solid compound of formula C4H5O2Na. When Z is heated with ethanoic acid and a few drops of concentrated sulphuric acid, a sweet smelling liquid of molecular formula C6H8O3 is formed. What functional group is shown to be present in Z by these tests? Tests for the third functional group. A few drops of Z form a yellow/orange precipitate when added to 2,4-dinitrophenylhydrazine reagent. When a few drops of Z are warmed with Tollens’ reagent, a silver mirror is formed. What functional group is shown to be present in Z by these tests? Z does not show cis-trans isomerism. Draw the displayed formula of Z. For Examiner’s Use For Examiner’s Use In parts and you may use R– to represent the part of the molecule that does not react. What is the organic compound formed by the reactions of Z in each of the tests in ? with sodium with ethanoic acid Draw the structure of the organic compound formed by Z in each of the tests in . with Tollens’ reagent with 2,4-dinitrophenylhydrazine, But-2-enoic acid is an isomer of Z which shows cis-trans isomerism. Draw a displayed formula of the cis isomer of this acid. NHNH2 NO2 NO2