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</div><h2>SL Paper 2</h2><div class="specification">
<p>Consider the following list of organic compounds.</p>
<p> Compound 1: \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{CH(OH)C}}{{\text{H}}_{\text{3}}}\)</p>
<p> Compound 2: \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{COC}}{{\text{H}}_{\text{3}}}\)</p>
<p> Compound 3: \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{OH}}\)</p>
<p> Compound 4: \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{CHO}}\)</p>
</div>
<div class="specification">
<p>Hydrochloric acid neutralizes sodium hydroxide, forming sodium chloride and water.</p>
<p style="text-align: center;">\({\text{NaOH(aq)}} + {\text{HCl(aq)}} \to {\text{NaCl(aq)}} + {{\text{H}}_{\text{2}}}{\text{O(l)}}\) \(\Delta {H^\Theta } = -57.9{\text{ kJ}}\,{\text{mo}}{{\text{l}}^{ - 1}}\)</p>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p>Apply IUPAC rules to state the name of compound 1.</p>
<div class="marks">[1]</div>
<div class="question_part_label">a.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p>(i) Define the term <em>structural isomers</em>.</p>
<p> </p>
<p> </p>
<p>(ii) Identify the two compounds in the list that are structural isomers of each other.</p>
<div class="marks">[2]</div>
<div class="question_part_label">b.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p>Determine the organic product formed when each of the compounds is heated under reflux with excess acidified potassium dichromate(VI). If no reaction occurs write NO REACTION in the table.</p>
<p style="text-align: center;"><img src="images/Schermafbeelding_2016-08-23_om_08.41.32.png" alt="N14/4/CHEMI/SP2/ENG/TZ0/07.c"></p>
<div class="marks">[4]</div>
<div class="question_part_label">c.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p>Explain the mechanism for the substitution reaction of bromoethane with sodium hydroxide. Use curly arrows to represent the movement of electron pairs.</p>
<div class="marks">[4]</div>
<div class="question_part_label">d.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p>(i) Define the term <em>standard enthalpy change of reaction</em>, \(\Delta {H^\Theta }\).</p>
<p> </p>
<p> </p>
<p> </p>
<p>(ii) Determine the amount of energy released, in kJ, when \({\text{50.0 c}}{{\text{m}}^{\text{3}}}\) of \({\text{1.00 mol}}\,{\text{d}}{{\text{m}}^{ - 3}}\) sodium hydroxide solution reacts with \({\text{50.0 c}}{{\text{m}}^{\text{3}}}\) of \({\text{1.00 mol}}\,{\text{d}}{{\text{m}}^{ - 3}}\) hydrochloric acid solution.</p>
<p> </p>
<p> </p>
<p> </p>
<p> </p>
<p>(iii) In an experiment, 2.50 g of solid sodium hydroxide was dissolved in \({\text{50.0 c}}{{\text{m}}^{\text{3}}}\) of water. The temperature rose by 13.3 °C. Calculate the standard enthalpy change, in \({\text{kJ}}\,{\text{mo}}{{\text{l}}^{ - 1}}\), for dissolving one mole of solid sodium hydroxide in water.</p>
<p>\[{\text{NaOH(s)}} \to {\text{NaOH(aq)}}\]</p>
<p>(iv) Using relevant data from previous question parts, determine \(\Delta {H^\Theta }\), in \({\text{kJ}}\,{\text{mo}}{{\text{l}}^{ - 1}}\), for the reaction of solid sodium hydroxide with hydrochloric acid.</p>
<p>\[{\text{NaOH(s)}} + {\text{HCl(aq)}} \to {\text{NaCl(aq)}} + {{\text{H}}_{\text{2}}}{\text{O(l)}}\]</p>
<div class="marks">[9]</div>
<div class="question_part_label">e.</div>
</div>
<br><hr><br><div class="specification">
<p>\({\text{25.0 c}}{{\text{m}}^{\text{3}}}\) of \({\text{0.200 mol}}\,{\text{d}}{{\text{m}}^{ - 3}}\) ethanoic acid were added to \({\text{30.0 c}}{{\text{m}}^{\text{3}}}\) of a \({\text{0.150 mol}}\,{\text{d}}{{\text{m}}^{ - 3}}\) sodium hydrogencarbonate solution, \({\text{NaHC}}{{\text{O}}_{\text{3}}}{\text{(aq)}}\).</p>
</div>
<div class="specification">
<p>The molar mass of a volatile organic liquid, <strong>X</strong>, can be determined experimentally by allowing it to vaporize completely at a controlled temperature and pressure. 0.348 g of <strong>X</strong> was injected into a gas syringe maintained at a temperature of 90 °C and a pressure of \(1.01 \times {10^5}{\text{ Pa}}\). Once it had reached equilibrium, the gas volume was measured as \({\text{95.0 c}}{{\text{m}}^{\text{3}}}\).</p>
</div>
<div class="specification">
<p>Bromoethane, \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{Br}}\), undergoes a substitution reaction to form ethanol, \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{OH}}\).</p>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p>Outline how electrical conductivity can be used to distinguish between a \({\text{0.200 mol}}\,{\text{d}}{{\text{m}}^{ - 3}}\) solution of ethanoic acid, \({\text{C}}{{\text{H}}_{\text{3}}}{\text{COOH}}\), and a \({\text{0.200 mol}}\,{\text{d}}{{\text{m}}^{ - 3}}\) solution of hydrochloric acid, HCl.</p>
<div class="marks">[1]</div>
<div class="question_part_label">a.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p>(i) State an equation for the reaction of ethanoic acid with a solution of sodium hydrogencarbonate.</p>
<p> </p>
<p> </p>
<p>(ii) Determine which is the limiting reagent. Show your working.</p>
<p> </p>
<p> </p>
<p> </p>
<p> </p>
<p>(iii) Calculate the mass, in g, of carbon dioxide produced.</p>
<div class="marks">[5]</div>
<div class="question_part_label">b.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p>(i) Determine the amount, in mol, of <strong>X </strong>in the gas syringe.</p>
<p> </p>
<p> </p>
<p> </p>
<p> </p>
<p> </p>
<p> </p>
<p>(ii) Calculate the molar mass of <strong>X</strong>.</p>
<div class="marks">[4]</div>
<div class="question_part_label">c.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p>(i) Identify the reagent necessary for this reaction to occur.</p>
<p> </p>
<p>(ii) Deduce the mechanism for the reaction using equations and curly arrows to represent the movement of electron pairs.</p>
<div class="marks">[4]</div>
<div class="question_part_label">d.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p>Determine the enthalpy change, in kJ mol\(^{ - 1}\), for this reaction, using Table 10 of the Data Booklet.</p>
<div class="marks">[3]</div>
<div class="question_part_label">e.ii.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p>Bromoethene, \({\text{C}}{{\text{H}}_{\text{2}}}{\text{CHBr}}\), can undergo polymerization. Draw a section of this polymer that contains six carbon atoms.</p>
<div class="marks">[1]</div>
<div class="question_part_label">f.</div>
</div>
<br><hr><br><div class="specification">
<p class="p1">Ethene belongs to the homologous series of the alkenes.</p>
</div>
<div class="specification">
<p class="p1">A bromoalkane, \({{\text{C}}_{\text{4}}}{{\text{H}}_{\text{9}}}{\text{Br}}\), reacts with a warm, aqueous sodium hydroxide solution, NaOH.</p>
</div>
<div class="specification">
<p class="p1">The time taken to produce a certain amount of product using different initial concentrations of \({{\text{C}}_{\text{4}}}{{\text{H}}_{\text{9}}}{\text{Br}}\) and NaOH is measured. The results are shown in the following table.</p>
<p class="p1" style="text-align: center;"><img src="images/Schermafbeelding_2016-09-14_om_16.46.57.png" alt="M13/4/CHEMI/SP2/ENG/TZ1/08.c"></p>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">Outline <strong>three </strong>features of a homologous series.</p>
<div class="marks">[3]</div>
<div class="question_part_label">a.i.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">Describe a test to distinguish ethene from ethane, including what is observed in <strong>each </strong>case.</p>
<div class="marks">[2]</div>
<div class="question_part_label">a.ii.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">Bromoethane can be produced either from ethene or from ethane. State an equation for <strong>each </strong>reaction.</p>
<div class="marks">[2]</div>
<div class="question_part_label">a.iii.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">State the equation for the reaction of \({{\text{C}}_{\text{4}}}{{\text{H}}_{\text{9}}}{\text{Br}}\) with NaOH.</p>
<div class="marks">[1]</div>
<div class="question_part_label">b.i.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">Suggest what would happen to the pH of the solution as the reaction proceeds.</p>
<div class="marks">[1]</div>
<div class="question_part_label">b.ii.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">Deduce the effect of the concentration of \({{\text{C}}_{\text{4}}}{{\text{H}}_{\text{9}}}{\text{Br}}\) and NaOH on the rate of reaction.</p>
<p class="p2"> </p>
<p class="p1">C<sub><span class="s1">4</span></sub>H<sub><span class="s1">9</span></sub>Br:</p>
<p class="p2"> </p>
<p class="p2"> </p>
<p class="p1">NaOH:</p>
<div class="marks">[2]</div>
<div class="question_part_label">c.i.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">Suggest why <strong>warm </strong>sodium hydroxide solution is used.</p>
<div class="marks">[1]</div>
<div class="question_part_label">c.ii.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">Deduce whether C<sub><span class="s1">4</span></sub>H<sub><span class="s1">9</span></sub>Br is a primary or tertiary halogenoalkane.</p>
<div class="marks">[2]</div>
<div class="question_part_label">c.iii.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">Determine the structural formula of C<sub><span class="s1">4</span></sub>H<sub><span class="s1">9</span></sub>Br.</p>
<div class="marks">[1]</div>
<div class="question_part_label">c.iv.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">Describe, using an equation, how \({{\text{C}}_{\text{4}}}{{\text{H}}_{\text{9}}}{\text{Br}}\) can be converted into \({{\text{C}}_{\text{4}}}{{\text{H}}_{\text{8}}}{\text{B}}{{\text{r}}_{\text{2}}}\).</p>
<div class="marks">[1]</div>
<div class="question_part_label">c.v.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">Explain the mechanism for the reaction in (c) of \({{\text{C}}_{\text{4}}}{{\text{H}}_{\text{9}}}{\text{Br}}\) with NaOH, using curly arrows to represent the movement of electron pairs.</p>
<div class="marks">[4]</div>
<div class="question_part_label">d.</div>
</div>
<br><hr><br><div class="specification">
<p class="p1">In an experiment to measure the enthalpy change of combustion of ethanol, a student heated a copper calorimeter containing 100 cm<sup><span class="s1">3 </span></sup>of water with a spirit lamp and collected the following data.</p>
<p class="p1">\[\begin{array}{*{20}{l}} {{\text{Initial temperature of water:}}}&{{\text{20.0 }}^\circ {\text{C}}} \\ {{\text{Final temperature of water:}}}&{{\text{55.0 }}^\circ {\text{C}}} \\ {{\text{Mass of ethanol burned:}}}&{{\text{1.78 g}}} \\ {{\text{Density of water:}}}&{{\text{1.00 g}}\,{\text{c}}{{\text{m}}^{ - 3}}} \end{array}\]</p>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">(i) Use the data to calculate the heat evolved when the ethanol was combusted.</p>
<p class="p1">(ii) Calculate the enthalpy change of combustion per mole of ethanol.</p>
<p class="p1">(iii) Suggest two reasons why the result is not the same as the value in the Data Booklet.</p>
<div class="marks">[6]</div>
<div class="question_part_label">a.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">Ethanol is part of the homologous series of alcohols. Describe <strong>two </strong>features of a homologous series.</p>
<div class="marks">[2]</div>
<div class="question_part_label">b.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">(i) Below are <strong>four structural </strong>isomers of alcohols with molecular formula \({{\text{C}}_{\text{4}}}{{\text{H}}_{{\text{10}}}}{\text{O}}\). State the name of each of the isomers <strong>a</strong>, <strong>b</strong>, <strong>c </strong>and <strong>D</strong>.</p>
<p class="p1" style="text-align: center;"><img src="images/Schermafbeelding_2016-10-07_om_09.52.00.png" alt="M10/4/CHEMI/SP2/ENG/TZ1/06.d"></p>
<p class="p1">(ii) <span class="Apple-converted-space"> </span>Determine the isomer that cannot be oxidized by acidifi ed potassium dichromate(VI), \({{\text{K}}_{\text{2}}}{\text{C}}{{\text{r}}_{\text{2}}}{{\text{O}}_{\text{7}}}\).</p>
<p class="p1">(iii) <span class="Apple-converted-space"> </span>Determine the isomer which can be oxidized to butanal.</p>
<p class="p1">(iv) <span class="Apple-converted-space"> </span>Determine the isomer which can be oxidized to butanone.</p>
<p class="p1">(v) <span class="Apple-converted-space"> </span>Suggest the structural formula of another isomer of \({{\text{C}}_{\text{4}}}{{\text{H}}_{{\text{10}}}}{\text{O}}\).</p>
<div class="marks">[8]</div>
<div class="question_part_label">c.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1" style="text-align: center;"><img src="images/Schermafbeelding_2016-10-07_om_09.52.00.png" alt="M10/4/CHEMI/SP2/ENG/TZ1/06.d"></p>
<p class="p1">(i) Isomer <strong>a </strong>is formed by reacting 1-bromobutane with aqueous sodium hydroxide. State whether the reaction would proceed via an S<sub><span class="s1">N</span></sub>1 or S<sub><span class="s1">N</span></sub>2 mechanism.</p>
<p class="p1">(ii) Explain the mechanism named in part (d) (i) using curly arrows to represent the movement of electron pairs.</p>
<div class="marks">[4]</div>
<div class="question_part_label">d.</div>
</div>
<br><hr><br><div class="specification">
<p class="p1">Alkenes, alcohols and esters are three families of organic compounds with many commercial uses.</p>
</div>
<div class="specification">
<p class="p1">Esters are often used in perfumes. Analysis of a compound containing the ester functional group only, gives a percentage composition by mass of C: 62.0% and H: 10.4%.</p>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">State the meaning of the term <em>structural isomers</em>.</p>
<div class="marks">[1]</div>
<div class="question_part_label">a.ii.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1"><strong>X </strong>is an isomer of C<sub><span class="s1">4</span></sub>H<sub><span class="s1">8 </span></sub>and has the structural formula shown below.</p>
<p class="p1" style="text-align: center;"><img src="images/Schermafbeelding_2016-09-23_om_13.10.03.png" alt="N12/4/CHEMI/SP2/ENG/TZ0/06.a.iii"></p>
<p class="p1">Apply IUPAC rules to name this isomer. Deduce the structural formulas of <strong>two</strong> other isomers of C<sub><span class="s1">4</span></sub>H<sub><span class="s1">8</span></sub>.</p>
<div class="marks">[3]</div>
<div class="question_part_label">a.iii.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">State the balanced chemical equation for the reaction of <strong>X </strong>with HBr to form <strong>Y</strong>.</p>
<div class="marks">[1]</div>
<div class="question_part_label">a.iv.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1"><strong>Y </strong>reacts with aqueous sodium hydroxide, NaOH(aq), to form an alcohol, <strong>Z</strong>. Identify whether <strong>Z </strong>is a primary, secondary or tertiary alcohol.</p>
<div class="marks">[1]</div>
<div class="question_part_label">a.v.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">Explain <strong>one </strong>suitable mechanism for the reaction in (v) using curly arrows to represent the movement of electron pairs.</p>
<div class="marks">[4]</div>
<div class="question_part_label">a.vi.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">Deduce the structural formula of the organic product formed when <strong>Z </strong>is oxidized by heating under reflux with acidified potassium dichromate(VI) <strong>and </strong>state the name of the functional group of this organic product.</p>
<div class="marks">[2]</div>
<div class="question_part_label">a.vii.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">Draw the ester functional group.</p>
<div class="marks">[1]</div>
<div class="question_part_label">b.i.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">Determine the empirical formula of the ester, showing your working.</p>
<div class="marks">[4]</div>
<div class="question_part_label">b.ii.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">The molar mass of the ester is \({\text{116.18 g}}\,{\text{mo}}{{\text{l}}^{ - 1}}\). Determine its molecular formula.</p>
<div class="marks">[1]</div>
<div class="question_part_label">b.iii.</div>
</div>
<br><hr><br><div class="specification">
<p class="p1">Chloroethene, C<sub><span class="s1">2</span></sub>H<sub><span class="s1">3</span></sub>Cl, is an important organic compound used to manufacture the polymer poly(chloroethene).</p>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">Draw the Lewis structure for chloroethene and predict the H–C–Cl bond angle.</p>
<div class="marks">[2]</div>
<div class="question_part_label">a.i.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">Draw a section of poly(chloroethene) containing six carbon atoms.</p>
<div class="marks">[1]</div>
<div class="question_part_label">a.ii.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">Outline why the polymerization of alkenes is of economic importance and why the disposal of plastics is a problem.</p>
<div class="marks">[2]</div>
<div class="question_part_label">a.iii.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">Chloroethene can be converted to ethanol in two steps. For each step deduce an overall equation for the reaction taking place.</p>
<p class="p1">Step 1:</p>
<p class="p1">Step 2:</p>
<div class="marks">[2]</div>
<div class="question_part_label">b.i.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">State the reagents and conditions necessary to prepare ethanoic acid from ethanol in the laboratory.</p>
<div class="marks">[2]</div>
<div class="question_part_label">b.ii.</div>
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<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">State an equation, including state symbols, for the reaction of ethanoic acid with water. Identify a Brønsted-Lowry acid in the equation and its conjugate base.</p>
<div class="marks">[3]</div>
<div class="question_part_label">b.iii.</div>
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<br><hr><br><div class="specification">
<p class="p1">Consider the following sequence of reactions.</p>
<p class="p1">\[{\text{RC}}{{\text{H}}_3}\xrightarrow{{reaction 1}}{\text{RC}}{{\text{H}}_2}{\text{Br}}\xrightarrow{{reaction 2}}{\text{RC}}{{\text{H}}_2}{\text{OH}}\xrightarrow{{reaction 3}}{\text{RCOOH}}\]</p>
<p class="p1">\({\text{RC}}{{\text{H}}_{\text{3}}}\) is an unknown alkane in which R represents an alkyl group.</p>
</div>
<div class="specification">
<p class="p1">The mechanism in <em>reaction 2 </em>is described as S<sub><span class="s1">N</span></sub>2.</p>
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<div class="specification">
<p class="p1">Propan-1-ol has two structural isomers.</p>
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<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">The alkane contains 81.7% by mass of carbon. Determine its empirical formula, showing your working.</p>
<div class="marks">[3]</div>
<div class="question_part_label">a.</div>
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<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">Equal volumes of carbon dioxide and the unknown alkane are found to have the same mass, measured to an accuracy of two significant figures, at the same temperature and pressure. Deduce the molecular formula of the alkane.</p>
<div class="marks">[1]</div>
<div class="question_part_label">b.</div>
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<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">(i) <span class="Apple-converted-space"> </span>State the reagent and conditions needed for <em>reaction 1</em>.</p>
<p class="p1">(ii) <span class="Apple-converted-space"> </span>State the reagent(s) and conditions needed for <em>reaction 3</em>.</p>
<div class="marks">[2]</div>
<div class="question_part_label">c.</div>
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<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1"><em>Reaction 1 </em>involves a free-radical mechanism. Describe the stepwise mechanism, by giving equations to represent the initiation, propagation and termination steps.</p>
<div class="marks">[4]</div>
<div class="question_part_label">d.</div>
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<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">(i) <span class="Apple-converted-space"> </span>State the meaning of each of the symbols in S<sub><span class="s1">N</span></sub>2.</p>
<p class="p1">(ii) <span class="Apple-converted-space"> </span>Explain the mechanism of this reaction using curly arrows to show the movement of electron pairs, and draw the structure of the transition state.</p>
<div class="marks">[4]</div>
<div class="question_part_label">e.</div>
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<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p class="p1">(i) <span class="Apple-converted-space"> </span>Deduce the structural formula of each isomer.</p>
<p class="p1">(ii) <span class="Apple-converted-space"> </span>Identify the isomer from part (f) (i) which has the higher boiling point and explain your choice. Refer to both isomers in your explanation.</p>
<div class="marks">[4]</div>
<div class="question_part_label">f.</div>
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<br><hr><br><div class="specification">
<p>Alkenes, such as <strong>A</strong> (shown below), are important intermediates in the petrochemical industry because they undergo addition reactions to produce a wide variety of products, such as the conversion shown below.</p>
<p style="text-align: center;"><img src="images/Schermafbeelding_2016-08-17_om_17.00.19.png" alt="M14/4/CHEMI/SP2/ENG/TZ2/06"></p>
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<div class="specification">
<p>Another way to make <strong>B</strong> is the reaction shown below.</p>
<p><img src="images/Schermafbeelding_2016-08-17_om_17.11.56.png" alt="M14/4/CHEMI/SP2/ENG/TZ2/06.c"></p>
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<div class="specification">
<p><strong>B </strong>can be converted into <strong>C</strong>.</p>
<p style="text-align: center;"><img src="images/Schermafbeelding_2016-08-17_om_17.16.54.png" alt="M14/4/CHEMI/SP2/ENG/TZ2/06.d"></p>
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<div class="specification">
<p>In the gas phase, <strong>A</strong> reacts with hydrogen to form <strong>D</strong>.</p>
<p style="text-align: center;"><img src="images/Schermafbeelding_2016-08-17_om_17.41.44.png" alt="M14/4/CHEMI/SP2/ENG/TZ2/06.g"></p>
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<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p>Applying IUPAC rules, state the name of <strong>A</strong>.</p>
<div class="marks">[1]</div>
<div class="question_part_label">a.</div>
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<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p>State the reagent required to convert <strong>A</strong> into <strong>B</strong>.</p>
<div class="marks">[1]</div>
<div class="question_part_label">b.</div>
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<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p>(i) State the conditions required for this reaction to occur.</p>
<p> </p>
<p>(ii) Outline why it would give a poor yield of the desired product.</p>
<div class="marks">[2]</div>
<div class="question_part_label">c.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p>(i) State the reagent required.</p>
<p> </p>
<p>(ii) Explain the mechanism of this reaction, using curly arrows to represent the movement of electron pairs.</p>
<div class="marks">[4]</div>
<div class="question_part_label">d.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p><strong>A </strong>can also be converted into <strong>C </strong>without going via <strong>B</strong>. State the reagent and conditions required.</p>
<div class="marks">[2]</div>
<div class="question_part_label">e.</div>
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<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p>(i) State why <strong>C </strong>is <strong>not </strong>readily oxidized by acidified potassium dichromate(VI).</p>
<p> </p>
<p> </p>
<p>(ii) Deduce the structural formula of an isomer of <strong>C </strong>that could be oxidized to a carboxylic acid by this reagent.</p>
<div class="marks">[2]</div>
<div class="question_part_label">f.</div>
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<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p>State the conditions required for this reaction to occur.</p>
<div class="marks">[1]</div>
<div class="question_part_label">g.i.</div>
</div>
<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p>State the homologous series to which <strong>D</strong> belongs.</p>
<div class="marks">[1]</div>
<div class="question_part_label">g.ii.</div>
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<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p>Determine the enthalpy change, in \({\text{kJ}}\,{\text{mo}}{{\text{l}}^{ - 1}}\), for the reaction of <strong>A</strong> with hydrogen, using Table 10 of the Data Booklet, and state whether the reaction is exothermic or endothermic.</p>
<div class="marks">[4]</div>
<div class="question_part_label">g.iii.</div>
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<div class="question" style="padding-left: 20px; padding-right: 20px;">
<p>The standard enthalpy change of combustion of <strong>A</strong> is \( - 4000{\text{ kJ}}\,{\text{mo}}{{\text{l}}^{ - 1}}\). Calculate the amount of <strong>A</strong>, in mol, that would have to be burned to raise the temperature of \({\text{1 d}}{{\text{m}}^{\text{3}}}\) of water from 20 °C to 100 °C.</p>
<div class="marks">[2]</div>
<div class="question_part_label">g.iv.</div>
</div>
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