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QUESTION 3 W z Ww xX \ | nf C=C |ÔøΩ> +CÔøΩC+ fo | | ej Z Y Z This general chemical equation represents the following type of reaction. (A) addition (B) hydrolysis (C) esterification (D) condensation
QUESTION 4 Oil of wintergreen is a chemical compound with the following chemical structure. OH Identify the functional groups present 1n oil of wintergreen. (A) alcohol and ester (B) alcohol and ketone (C) alcohol and aldehyde (D) alcohol and carboxylic acid
QUESTION 8 An organic compound X reacts with sodium hydrogen carbonate to form carbon dioxide gas. Compound X is (A) an amine. (B) ahaloalkane. (C) acarboxylic acid. (D) aprimary alcohol
QUESTION 12 Apply IUPAC rules to name the molecule. (A) cisÔøΩ2ÔøΩpentene (B) ÔøΩtransÔøΩ2ÔøΩpentene (C) cisÔøΩlÔøΩethylÔøΩ2ÔøΩmethylethene (D) transÔøΩ|ÔøΩethylÔøΩ2ÔøΩmethylethene
QUESTION 15 This compound is an unsaturated fatty acid because it contains a (A) double bond and a carboxylic acid group. (B) long carbon chain and a carboxylic acid group. (C) double bond an aldehyde group and a hydroxyl group. (D) long carbon chain an aldehyde group and a hydroxyl group
QUESTION 16 CH CN + 2H ÔøΩ$ CH;CH NH The reaction shows (A) an addition reaction that converts an amine to a nitrile. (B) areduction reaction that converts a nitrile to an amine. (C) an oxidation reaction that converts an amine to a nitrile. (D) asubstitution reaction that converts a nitrile to an amine
QUESTION 19 Dispersion forces hydrogen bonding disulfide bridges and ionic bonding all contribute to the (A) primary structure of proteins. (B) secondary structure of proteins. (C) tertiary structure of proteins. (D) quaternary structure of proteins
QUESTION 21 (5 marks) a) Glucose is an example of which type of carbohydrate? [1 mark] b) Starch and cellulose are both polymers of glucose. Compare the structure of starch and cellulose in terms of their glycosidic links. [4 marks]
QUESTION 26 (5 marks) The mass and infrared spectra for an organic compound X with the empirical formula C;H O are shown. Mass spectrum 100 43 nN oo So on) & ÔøΩ Relative intensity 20 / 0.0 20 40 60 80 100 m/z Infrared spectrum S ÔøΩ oy (oe) Oo IN Relative transmittance 0.2 3000 2000 1000 Wavenumber (cm!) Analyse the spectra to deduce the structural formula of X. Explain your reasoning
QUESTION 2 (12 marks) Salicylic acid reacts with ethanoic anhydride in an aqueous solution to produce acetylsalicylic acid as shown in the equation. Acetylsalicylic acid is commonly known as aspirin. a) b) Cc) d) e) O On i O C CH /&ÔøΩ CH 3 7 ÔøΩ + CÔøΩOH As = CH-CÔøΩOH I ee: CÔøΩOH 3 O salicylic acid ethanoic anhydride acetylsalicylic acid ethanoic acid (C H 05) (C H 03) (C H O0 ) (C H 0 ) Identify the type of chemical reaction used to produce aspirin. [1 mark] Write the equilibrium expression K for the reaction. [1 mark] At 20 ÔøΩC the equilibrium constant (K ) for the reaction is 2 x 10ÔøΩ. Determine whether the concentration of the reactants or products is greater at equilibrium at this temperature. [2 marks] Calculate the minimum mass of salicylic acid required to produce 500.0 mg of aspirin if the yield of aspirin 1s 45.0%. Show your working. [4 marks] mg (to three significant figures) When the reaction is heated to 40 ÔøΩC and equilibrium is re-established the concentration of acetylsalicylic acid and ethanoic acid increases. Apply Le ChatelierÔøΩs principle to predict if the forward reaction is exothermic or endothermic. Explain your reasoning. [4 marks]
QUESTION 3 (9 marks) Ethanol can be produced by the fermentation of glucose or the hydration of ethene. a) Describe the production of ethanol by fermentation of glucose by writing a balanced equation and indicating if a catalyst is required. b) Calculate the atom economy for the production of ethanol by fermentation of glucose. Atom economy = c) Interms of atom economy determine which process for the production of ethanol (i.e. hydration of ethene or fermentation of glucose) is greener. d) Identify two principles of green chemistry other than atom economy that make the production of ethanol by fermentation greener than by hydration. [3 marks] [2 marks] [2 marks] [2 marks]
QUESTION 4 (10 marks) Consider the organic molecule shown. a) b) c) d) e) H.C * ÔøΩC=CH HCÔøΩ Identify the molecule as saturated or unsaturated. Apply IUPAC rules to name this molecule. Write an equation to show the products formed by the hydration of this molecule. Predict which is the major product formed in c). Identify a physical property and experimental technique that could be used to separate products formed by hydration in c). Explain your reasoning. [1 mark] [1 mark] [2 marks] [1 mark] [5 marks]
QUESTION 5 (17 marks) Compound A reacts with water to produce compound B and hydroxide ions. a) b) c) d) e) CH CH NH (aq) +H O(l) f C HsNH{ (aq) + OH (aq) A B Apply IUPAC rules to name compound A. Identify the Brensted-Lowry acids in the equation. A small amount of hydrochloric acid is added to the equilibrium mixture. Predict the effect of this on the concentration of compound A in the mixture. Explain your reasoning. Calculate the pH of a 2.0 M solution of compound A. State any assumptions. Show your working. (K =5.6x10-*) (to one decimal place) Describe using a balanced chemical equation how Compound A could be made from bromomethane. Include relevant conditions and reagents in your response. [1 mark] [2 marks] [3 marks] [6 marks] [5 marks]
QUESTION 2 Intra-chain hydrogen bonding between peptide groups occurs in (A) (B) (C) (D) primary protein structures. secondary protein structures. tertiary protein structures. quaternary protein structures
QUESTION 4 The cleaning action of soap is impaired in hard water because the (A) hydrophilic end reacts with calcium ions to form insoluble salts. (B) hydrophobic end reacts with calcium ions to form insoluble salts. (C) hydrophilic end reacts with calcium ions to form insoluble fatty acids. (D) hydrophobic end reacts with calcium ions to form insoluble fatty acids
QUESTION 7 Identify which molecule is an amide. (A) (B) (C) (D) CH;CH CN CH; CH NH NH CH; COO CH CONHCH
QUESTION 8 Electric current id Air in Ja O and other gases in Unused Wily <7 Excess fuel gases out = Anode Electrolyte Cathode Identify the operating conditions for the hydrogen fuel cell. (A) acidic conditions with hydrogen given off as an unused gas (B) alkaline conditions with hydrogen given off as an unused gas (C) acidic conditions with hydrogen ions present in the electrolyte (D) alkaline conditions with hydrogen ions present in the electrolyte
QUESTION 9 The boiling points of methane ethane and propane increase as the lengths of the carbon chains increase because more energy is required to overcome the (A) intramolecular hydrogen bonds. (B) intermolecular hydrogen bonds. (C) intramolecular dispersion forces. (D) intermolecular dispersion forces
QUESTION 11 Enzymes can act as biological catalysts because they (A) can be denatured. (B) lower the activation energy. (C) are sensitive to pH and temperature changes. (D) increase the equilibrium constant for the reaction
QUESTION 12 Green chemistry principles include the design of chemical synthesis processes that (A) use renewable raw materials and minimise unwanted products. (B) use renewable raw materials and minimise unwanted reactants. (C) use non-renewable raw materials and minimise unwanted products. (D) use non-renewable raw materials and minimise unwanted reactants
QUESTION 13 Infrared spectrum Relative transmittance 3000 2000 1000 Wavenumber (cm7!) Determine the functional group present in the infrared spectrum. (A) ester (B) ketone (C) alcohol (D) carboxylic acid
QUESTION 15 Which organic compound has the highest boiling point? (A) (B) (C) (D) CH3(CH2)3CH3 CH (CH );CHO CH CH(CH;) CH; CH;(CH );CH OH
QUESTION 16 Calculate the percentage yield of magnesium ethanoate when 8.0 moles of ethanoic acid reacts with 6.0 moles of magnesium carbonate producing 3.5 moles of magnesium ethanoate as shown in the equation. 2CH;COOH(aq) + MgCO (s) > (CH;COO) Mg(aq) + CO (g) + H5O(1) (A) 44% (B) 58% (C) 88% (D) 100%
QUESTION 18 Identify the major product when 2-methylbut-2-ene reacts with water under acidic conditions. (A) (CH ) CHCOCH (B) (CH3) C(OH)CH CH3 (C) (CH ) CHCHOH)CH; (D) (CH3) C(OH)CH(OH)CH
QUESTION 19 To form ethanol biofuel in the fermentation of glucose a catalyst is used because (A) (B) (C) (D) less energy is required and the rate of reaction is increased. less energy is required and the rate of reaction is decreased. more energy is required and the rate of reaction is increased. more energy 1s required and the rate of reaction is decreased
QUESTION 20 Identify the ester linkage in aspartame. (A) O Cc) N H (B) O 6S NN N H OH NH (C) (D) O N H
QUESTION 22 (4 marks) The structural formula for pentane (C;H ) is shown. H H H H H Pot tt HÔøΩCÔøΩCÔøΩCÔøΩCÔøΩCÔøΩH Draw the structural formulas for two structural isomers of pentane. Name each isomer. a) Isomer 1 [2 marks] Note: If you make a mistake in the drawing cancel it by ruling a single diagonal line through your work and use the additional response space on page 16 of this question and response book. IUPAC name: b) Isomer 2 [2 marks] Note: If you make a mistake in the drawing cancel it by ruling a single diagonal line through your work and use the additional response space on page 16 of this question and response book. IUPAC name:
QUESTION 23 (5 marks) Aspartame is a methyl ester of a dipeptide that hydrolyses to form methanol and two amino acids. The structure of aspartame is shown. O OCH3 Zz OH NHÔøΩ O a) Identify the two amino acids that form aspartame. [1 mark] A hydrolysed sample of aspartame was analysed with silica thin layer chromatography (TLC) using a mixture of butanol and ethanoic acid as the solvent. The TLC plate was then reacted with ninhydrin to produce spots. Key S = hydrolysed aspartame sample Spot A TTT > R = reference amino acid 1 Spot B R = reference amino acid 2 R; = isoleucine b) Determine which amino acid in aspartame corresponds to Spot A. Explain your reasoning. [3 marks] c) Explain why the reference amino acids are included on the TLC plate. [1 mark]
QUESTION 2 (10 marks) Polypropene (PP) is a polymer formed from propene. Polyethylene terephthalate (PET) is a polymer formed from monomers of carboxylic acid and alcohol. A section of the PET polymer is shown. a) O O \ Ih 7 \ O OÔøΩÔøΩCH ÔøΩÔøΩCH n Draw the structural formulas of the monomers used to form PET. [2 marks] 1) Carboxylic acid monomer 11) Alcohol monomer Note: If you make a mistake in the drawing cancel it by ruling a single diagonal line through your work and use the additional response space on page 16 of this question and response book. Determine the type of polymerisation used to form PET. [1 mark] Identify the functional group formed by the reaction of the monomers in PET. [1 mark] Determine the type of polymerisation used to form PP. [1 mark] Explain how the position of the methyl group on the polymer chain affects the strength of isotactic PP relative to syntactic PP. [5 marks]
QUESTION 3 (11 marks) Four colourless liquids A B C and D are known to be butane 1-butene 2-butanol and 1-propanol. Reactions are carried out to identify the liquids. The results are shown. a Excess acidified potassium Decolourised Decolourised No reaction manganate(VIT) (KMnO ) Compound X Compound Y solution heated gently formed formed Ethanol and concentrated Fruity smell No apparent sulfuric acid solution heated | produced reaction gently and refluxed Compound Z formed a) Identify Compound D. Explain your reasoning. [2 marks] b) Write a balanced equation to describe the decolourisation of bromine (Br) water by Compound D. Apply IUPAC rules to name the product formed. [2 marks] IUPAC name: c) Identify Compound C. Explain your reasoning. [3 marks] d) Draw the structural formula of Compound Y. [1 mark] Note: If you make a mistake in the drawing cancel it by ruling a single diagonal line through your work and use the additional response space on page 17 of this question and response book. e) Identify Compound B. [1 mark] f) Draw the structural formula of Compound Z. [1 mark] Note: If you make a mistake in the drawing cancel it by ruling a single diagonal line through your work and use the additional response space on page 17 of this question and response book. g) Apply IUPAC rules to name Compound Z. [1 mark] IUPAC name:
QUESTION 1 Identify the type of reaction that occurs when ethene undergoes polymerisation to form polyethene. (A) addition (B) elimination (C) substitution (D) condensation
QUESTION 2 Structural isomers are compounds with the same molecular formula but a different (A) molar mass. (B) molecular mass. (C) empirical formula. (D) arrangement of atoms
QUESTION 4 Which pair of reagents would react to form a glycosidic bond? (A) lysine and aniline (B) glucose and galactose (C) methanol and butanoic acid (D) glycerol and sodium hydroxide
QUESTION 5 Phosphorus pentoxide is prepared by burning phosphorus in oxygen. P4(s) + 509(g) > P4Oj0(s) Calculate the percentage yield if 10.0 g of P4Oj9 is produced when 0.200 mol of P and 0.200 mol of O are reacted. (A) 2.0% (B) 3.5% (C) 17.6% (D) 88.0%
QUESTION 7 Alcohol Compound X Compound X Compound X in these reaction pathways is (A) aketone. (B) an alkene. (C) an aldehyde. (D) acarboxylic acid
QUESTION 9 The IUPAC name for this molecule is (A) 2-chloro-3-fluorobutane. (B) 2-fluoro-3-chlorobutane. (C) 2-dimethyl-1-chloro-2-fluoroethane. (D) 1 2-dimethyl-1-fluoro-2-chloroethane
QUESTION 14 The mass spectrum for Compound X is found to have signals at the following m/z values. Mass spectrum 100 80 60 40 Relative intensity (%) 20 10 20 30 40 50 60 70 80 m/z Compound X is (A) butanal. (B) butanol. (C) butanone. (D) butanoic acid
QUESTION 15 The structure of an amino acid is shown. OH HN This molecule contains an amine group and a (A) carboxyl group. (B) hydroxy group. (C) methyl group. (D) ketone group
QUESTION 20 CHs CHs 1 (CH CH ÔøΩ CHÔøΩ CH cH CH ÔøΩ CHÔøΩ CH cH ) CH; CH; CH; CH; | | CH CH The two forms of polypropene shown are (A) syntactic atactic (B) isotactic atactic isotactic syntactic atactic syntactic
QUESTION 21 (4 marks) a) Identify whether 2-bromopropane is a saturated or unsaturated compound. Explain your reasoning. [2 marks] b) Determine whether 2-bromopropane is a primary secondary or tertiary halogenoalkane. Explain your reasoning. [2 marks]
QUESTION 23 (4 marks) Ibuprofen is manufactured using two different processes. Number Ibuprofen Waste products ot Atoms M Atoms M . Atoms M . reagents used 2 [fetid | 2560] CuthsOs | 2060 G0 | 600 Calculate the atom economy for each process and draw conclusions about the economic and environmental impact of each process.
QUESTION 1 (8 marks) The diagram shows a series of different reactions starting with compound A which has the empirical formula C H 0. H 0/H B (alkene) CandA H SO (catalyst) at a temperature > 170ÔøΩC P Cr 0 i H* Cr 0 | HÔøΩ A D E (butanoic acid) CH COOH / Ht F (ester) a) Identify the class of organic compounds that compound A belongs to. [1 mark] b) Compound C is an isomer of compound A. Deduce the structural formulas and IUPAC names of compounds A and C. [4 marks] 1) Compound A Note: If you make a mistake in the drawing cancel it by ruling a single diagonal line through your work and use the additional response space at the back of this question and response book. IUPAC name: 11) Compound C Note: If you make a mistake in the drawing cancel it by ruling a single diagonal line through your work and use the additional response at the back of this question and response book. IUPAC name: c) Identify whether compounds A and C are structural or geometric isomers. [1 mark] d) Deduce the structural formula and IUPAC name for compound F. [2 marks] Compound F Note: If you make a mistake in the drawing cancel it by ruling a single diagonal line through your work and use the additional response space at the back of this question and response book. IUPAC name:
QUESTION 4 (8 marks) Bioethanol is a renewable energy source made from biomasses such as starch and cellulosic materials. The two-step process for the conversion of starch and cellulose to bioethanol is shown. Process | Step 1 Step 2 Conversion | Production to glucose process Starch Enzymatic hydrolysis Fermentation of glucose to Easier Faster (aÔøΩamylase) of starch form bioethanol (yeast) biomass to form glucose Cellulose | Acid hydrolysis (H SO (aq) | Fermentation of glucose to Harder Slower at 320 ÔøΩC and 25 MPa) of form bioethanol (yeast) cellulose biomass to form glucose a) Identify why it is important to control the temperature during the fermentation process to produce bioethanol. [2 marks] b) Explain why cellulose is harder to convert to glucose than starch. [3 marks] c) After 48 hours of fermentation a 15% w/v glucose solution produces 37.5 g L! of ethanol. Calculate the percentage yield of ethanol. Show your working. [3 marks] Ethanol yield = % (to one decimal place)
QUESTION 6 (8 marks) Polypeptides and proteins are formed by condensation reactions of amino acids. a) Identify the type of bond formed when three amino acids are joined to form a tripeptide and state any other product/s formed. [2 marks] b) Determine the total number of tripeptides that can be formed containing histidine lysine and glycine and use the three-letter symbols for the amino acids to describe two of the tripeptides formed. [3 marks] c) Explain how the pH of the buffer solution can be used to separate histidine lysine and glycine through electrophoresis. [3 marks]
QUESTION 12 Enzymes are classified as (A) carbohydrates. (B) proteins. (C) starches. (D) lipids.
QUESTION 2 (3 marks) Compare the structure of a-helix and B-pleated sheets in the secondary structure of proteins. Similarity: Difference: Significance:
QUESTION 23 (6 marks) The diagram represents a hydrogen fuel cell with an acid electrolyte. Proton exchange membrane a) H (g) O»(g) ! Product Z | (a) Determine the redox half-equation occurring at the anode and cathode. [2 marks] Anode half-equation: Cathode half-equation: (b) Identify product Z. [1 mark] (c) Compare the movement of electrons and hydrogen ions in the fuel cell. [3 marks] Similarity: Difference: Significance:
QUESTION 9 (4 marks) Aspirin (Cy)HgO ) can be produced from a reaction between salicylic acid (Cj;H O3) and acetic anhydride (C H O3) with ethanoic acid being a minor product. C7H6O03(s) + CyHe¢O3(aq) — CoHgOq(s) + C H4O>(aq) Calculate the mass of salicylic acid required to produce 8.25 g of aspirin if the percentage yield of the reaction is 60%. Show your working.
QUESTION 6 (6 marks) The reaction shows the base hydrolysis (saponification) of a triglyceride to produce glycerol and a soap. O CH —O— { — (CH) 4— CH; CH —OH O O CHO (CH>);4-CH ; + 3NaO0H -— > CH—OH + 3H C—(CH )q—C—ONa 9 CH —O— ( — (CH) 4—CH3 CH —OH Triglyceride Glycerol Soap (a) Identify which compound in the reaction is an ester. [1 mark] (b) Contrast the structure of saturated and unsaturated fatty acids. [1 mark] (c) Explain how the cleaning action of soap is related to its structure. [4 marks]
QUESTION 26 (5 marks) The table shows a series of reactions that were performed to produce organic compounds A B and C. conc. H SO (aq) / heat compound A and water H O(g) / heat compound B and propanol (4) KN (a) Determine the IUPAC name for compound A. [1 mark] IUPAC name: (b) Explain one structural difference between compound B and propanol. [2 marks] (c) Deduce the structural formula of compound C. [1 mark] (d) Describe one qualitative observation that would be expected for reaction 3. [1 mark]
QUESTION 17 Determine the functional group present in Product X. O I H * R—C—-O—-H + H—-O-R == Carboxylic acid Alcohol (A) ester (B) ketone (C) alcohol (D) aldehyde === S— === SSS==4 Di ei Ss
QUESTION 13 Identify the reaction used to produce methanol and triglycerides. (A) oxidation (B) substitution (C) saponification (D) transesterification
QUESTION 19 Identify the polymer shown. CH; (A) polyethene (B) polypeptide (C) polypropene (D) polysaccharide
QUESTION 22 (4 marks) (a) Write a balanced chemical equation to describe how polytetrafluorethene (PTFE) is produced from its monomer. [2 marks] (b) Determine whether polytetrafluorethene is an addition or condensation polymer. Explain your reasoning. [2 marks]
QUESTION 25 (7 marks) During the contact process for manufacturing sulfuric acid sulfur dioxide (SO ) and oxygen (O ) are passed over a vanadium oxide catalyst to produce sulfur trioxide (SO3). In the process the vanadium oxide undergoes the following reactions. Reaction 1: SO (g) + V 0;(s) > SO3(g) + V»O (s) Reaction 2: 2V 0 (s) + O (g) — 2V 0;(s) Overall reaction: 2SO3(g) + 05(g) —225 5 280 (g) (a) Determine the oxidation state of vanadium in V 0 (s). [1 mark] (b) Determine if vanadium in V O (s) in reaction | is acting as an oxidising or reducing agent. Explain your reasoning. [2 marks] (c) Use the reactions provided to explain why V O (s) 1s a catalyst for the overall reaction. [4 marks]
QUESTION 4 (8 marks) Compound C has the molecular formula C H O and is either an alcohol an aldehyde or a carboxylic acid. Compound C infrared spectrum JIY 0.8 oO = 0.6 pir 5 : ea 0.4 0.2 3000 2000 1000 Wavenumber (cm ') (a) Deduce the class of compound C. Explain your reasoning. [4 marks] (b) Deduce the structural formula and IUPAC name of two isomers of compound C. [2 marks] (c) Distinguish between structural and geometric isomers. [2 marks]
QUESTION 16 Haloalkanes undergo a substitution reaction with cyanide (CN _) in ethanol to produce (A) alkanes. (B) amines. (C) nitriles. (D) esters.
QUESTION 6 Identify the reactants that undergo a condensation reaction to produce the molecule shown. O | H;C — CH — CH —C—N— CH — CH — CH | H (A) 1-butanol and propanamine (B) 1-propanol and butanamine (C) butanoic acid and propanamine (D) propanoic acid and butanamine
QUESTION 14 Identify which molecule has the lowest boiling point. (A) butanone (B) hexanone (C) pentanone (D) propanone
QUESTION 20 The structural formula for a polypeptide is shown. N HN Os | H Identify the three amino acids present from left to right. (A) Arg Cys Met (B) Asp Cys Ala (C) Glu Cys Asp (D) Ile Cys Gly
QUESTION 18 Identify the reaction used to produce X. O | ee R-C—O—-H + H—-O—-R >= =e: ProductX | + H—-O—H Carboxylic acid Alcohol | Water (A) addition (B) hydration (C) condensation (D) hydrogenation
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