9701_w19_qp_21
A paper of Chemistry, 9701
Questions:
4
Year:
2019
Paper:
2
Variant:
1

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Crude oil is a natural source of hydrocarbons that are used as fuels. Hydrocarbons with low relative molecular mass, Mr, are used as fuels in industry, in the home and for transport. There is a high demand for the hydrocarbons with low Mr. Name the process by which long-chain hydrocarbons are broken down into shorter-chain hydrocarbons. Give one reason why hydrocarbons with low Mr are suitable for use as fuels. Incomplete combustion of hydrocarbons can release carbon monoxide, CO, into the atmosphere. Write an equation for the formation of CO from the incomplete combustion of butene, C4H8. Identify an analytical technique that can be used to monitor the levels of CO in the atmosphere. Outline how this analytical technique may be used to monitor the levels of CO. Thiophene, C4H4S, is an organic compound that is found as a contaminant in crude oil. Construct the equation for the complete combustion of thiophene, C4H4S. Include state symbols in your answer. A student carries out an experiment to determine the enthalpy change of combustion of C4H4S. Explain the meaning of the term enthalpy change of combustion. The student uses the following apparatus in the experiment. thermometer water copper container fuel burner containing C4H4Smass of water in copper container / g initial temperature of water / °C 18.5 highest temperature of water / °C 37.5 Calculate the heat energy released, in J, by the reaction. Assume that 4.18 J of heat energy changes the temperature of 1.0 cm3 of water by 1.0 °C. Assume no heat is lost to the surroundings.  heat energy released = J  The student used 0.63 g of C4H4Sin the experiment. Calculate the enthalpy change of combustion of thiophene, ΔHc(C4H4S). Include a sign in your answer. ΔHc(C4H4S) = kJ mol–1  
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(CH3)3CCHO is used in the synthesis of some antibiotics. Give the name of (CH3)3CCHO. State the hybridisation of the carbon atom labelled with an asterisk, *. CH3 CH3 H3C C C O H * Two reaction sequences are shown. CH3 CH3 NaBH4 H3C C S (CH3)3CCO2H A U C O H T reaction 2 reaction 3 reaction 1 [O] O O Reaction1 is an oxidation reaction. Identify the reagentand conditions for reaction1. A, (CH3)3CCO2H, is a solid at room temperature. B, CH3CO2(CH2)2CH3, is an isomer of A. B is a liquid at room temperature. Explain the difference in the physical states of A and B, with reference to any intermolecular forces that may exist. Give the balanced equation for the reaction of (CH3)3CCHO with NaBH4 to form S. Use [H] to represent an atom of hydrogen provided by NaBH4. Draw the structure of the organic molecule T that reacts with A, (CH3)3CCO2H, in reaction2, to form U. Suggest a catalyst for reaction2. T catalyst  X, Y and Z are all isomers of (CH3)3CCHO. A summary of some of the reactions and properties of X, Y and Z is shown in the table. compound observations with 2,4-DNPH observations with Fehling’s solution principal absorptions in infra-red spectrum X no reaction 1715 cm–1 Y red precipitate 1730 cm–1 Z no reaction no reaction 3200–3600 cm–1 1630 cm–1 1050 cm–1 X and Y each contains a carbonyl group. Complete the table with the expected observations for the reactions of X and Y with 2,4‑DNPH. Identify the functional group present in Y that causes the recorded observation with Fehling’s solution. Y has a chiral centre and exists as a pair of optical isomers. State what is meant by the term chiral centre. Draw the optical isomers of Y using the conventional three-dimensional representation.  Z, C5H10O, has a branched carbon chain. It shows geometrical isomerism. Complete the table with the bond responsible for each of the principal absorptions seen in the infra-red spectrum of Z. principal absorptions in infra-red spectrum bond responsible 3200–3600 cm–1 1630 cm–1 1050 cm–1  Draw the skeletal formula of Z.  X contains a carbonyl group. X reacts with HCN, in the presence of a small amount of NaCN, to form (C2H5)2C(OH)CN as shown. X + HCN (C2H5)2C(OH)CN Draw the mechanism of the reaction of X with HCN. ● Draw the structure of X and the intermediate. ● Include all charges, partial charges, lone pairs and curly arrows. C C2H5 C2H5 HO NC  State the role of NaCN in the reaction in .