Assessment Schedule Chemistry 2.5 90309 Describe the structural formulae and reactions of compounds containing selected organic functional groups. While the writers of this assessment have worked to compile a resource that meets NCEA requirements, it has no official status and teachers may wish to adjust questions and the assessment schedule as they see fit. Question ONE 1 Evidence (a) (b) (c) Achievement methanol 2-bromobutane 3-chloropropene (d) 4 correct answers. Merit 6 correct answers. OH CH3 C (e) H C O C CH3 (f) O CH2 CH3 CH3 CH2 CH2 C O TWO 1 Cl H Cl Cl Cl C C H H C C H H H H H 1,1-dichloroethane 2 3 THREE 1,2-dichloroethane No, there needs to be a double C=C bond to restrict rotation about the carbon-carbon bond CH3CH2OH ethanol 1 CH3CH2Br 2 CH3CH=CH2 3 CH3 Both formulae correct. Both names correct. No – plus mention of double bond. Formula and name correct. 3 correct answers. CH CH CH3 OH OH 4 FOUR 1 CH3CH2CH2CH2CO2H Cl H Cl H Cl H ~C C C C C C~ H H H H H H Correct structure. Complete answer including non-rotation. 4 correct answers. Excellence 2 Q Five 1&2 Evidence CH3 CH CH3 OH propan-2-ol CH3 CH2 CH2 OH propan-1-ol Achievement 1 name and formula. Merit Both names and formulae plus correct identification of major product. Unsymmetrical recognised Partial explanation Propan-2-ol is the major product 3 SIX 1(a) The requirements are that the alkene be unsymmetrical around the double bond with an unsymmetrical reagent adding on to it. CH3CH2CH2CH2CH=CH2 + Br2 Excellence Clear explanation including both molecules being unsymmetrical. Correct equation CH3CH2CH2CH2CH(Br)–CH2Br . 1(b) (i) Bromine changes from orange to colourless One observation Two observations One reason Two reasons Method and observation: only one compound referred to. Method and observation described for both compounds. One correct. Both correct. Ester is insoluble in water. Detail of difference in solubility. (ii) two colourless layers remain 1(c) (i) Bromine reacts with hexene in an addition reaction and a colourless product is formed. (ii) Organic product is insoluble in water so two layers form. 2 Reagent: Cr2O72–/H+ Obs: Reagent turns orange to green with ethanol; no change with ethanoic acid Reason: Ethanol can be oxidised ethanoic acid is not oxidised Full answer including explanation OR CO32– or active metal No reaction with ethanol; fizzing with ethanoic acid. Reason: Ethanoic acid shows typical acid properties; ethanol does not show acid properties. OR: moist litmus (or other indicator) No change in colour with ethanol. Ethanoic acid will change the colour of acid-base indicators. Reason: Ethanoic acid shows typical acid properties; ethanol does not show acid properties. SEVEN 1 (a) Catalyst/speeds up the reaction (b) To neutralise any remaining acid. 2 (a) & (b) 3 The ester is insoluble in water while methanol and propanoic acid are soluble in water. Hence the reactants dissolve in the water and the ester forms a separate upper layer because it is less dense than water. CH3OH + CH3CH2CO2H CH3 O C CH2 CH3 + H2O Equation without H2O O 4 Sweet/fruity smell correct Correct Full discussion on solubility plus density. 3 Sufficiency Statement. These exams are not pre-tested. The statements below are a guide and schools should feel free to adjust them to get a sensible distribution. Achieved Merit Excellence A total of EIGHT opportunities answered correctly at Achieved or higher. A total of TEN opportunities answered correctly with 4 at Merit and 6 at Achieved A total of TWELVE opportunities answered correctly with 2 at Excellence, 4 at Merit and 6 at Achieved.