Module Chemistry 'A'cceleration STPM 2023

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin STPM: Organic Chemistry 2022/2023 Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin Section A Answer all questions. 14 Introduction to Organic Chemistry 2 Vitamin C has the following structure. How many chiral centres are there in one molecule? A 1 B 2 C 3 D 4 14 Introduction to Organic Chemistry 3 Which alkene will form a ketone when heated with acidified KMnO4 solution? A CH3CH2CH=CH2 B CH3CH=CHCH2CH3 C CH3CH2CH=CHCH2CH3 D (CH3)2=CHCH3 14 Introduction to Organic Chemistry (Alkanes) 1 An energy level diagram for a single reaction step is shown below. To which of the following steps in the reaction of methane with chlorine in the presence of light does this diagram apply? A CH2Cl• + Cl2 → CH2Cl2 + Cl• B CH3• + CH3• → C2H6 C Cl2 → Cl• + Cl• D CH3Cl → CH3 + + Cl-

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 14 Introduction to Organic Chemistry 4 Which is not true about an electrophile? A It is a Lewis base. B It is involved in the Friedel-Crafts reaction. C It is an electron pair acceptor. D It is formed during heterolytic fission of covalent bond. 14 Introduction to Organic Chemistry 5 P and Q are two hydrocarbons with empirical formulae CH2 and CH respectively. Under the same conditions, P decolourises bromine water while Q does not. Which mechanism are correct about the reactions of P and Q? P Q A Electrophilic addition Electrophilic substitution B Electrophilic addition Nucleophilic substitution C Nucleophilic substitution Nucleophilic substitution D Electrophilic substitution Electrophilic substitution 14 Introduction to Organic Chemistry 6 Ethylbenzene reacts with concentrated nitric acid and concentrated sulphuric acid followed by acidified potassium manganate (VII). What is the structural formula of product formed? A B C D

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 14 Introduction to Organic Chemistry 7 When aqueous bromine is added to an organic compound Y, the colour of bromine is discharged. To which classes of compound could Y belong? I Alkene II Phenol III Haloalkane IV Aliphatic alcohol A I and II only B I and III only C II and III only D II and IV only 14 Introduction to Organic Chemistry 8 Which reaction represents a substitution reaction which occurs through electrophilic mechanism? A B C D 14 Introduction to Organic Chemistry 9 Which is not true about an electrophile? A It is a Lewis base. B It is involved in the Friedel-Crafts reaction. C It is an electron pair acceptor. D It is formed during heterolytic fission of covalent bond.

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 15 Hydrocarbon (Alkanes) 10 Naphthalene is an active component in mothballs. Its structural formula is shown below. How many hydrogen atoms are there in the molecule? A 8 B 10 C 11 D 12 15 Hydrocarbon 11 What is the volume of oxygen needed for a complete combustion that involves 5 cm3 of CH4 and 5 cm3 of C2H4? A 10 cm3 B 15 cm3 C 20 cm3 D 25 cm3 15 Hydrocarbon 12 What is the volume of oxygen needed for a complete combustion that involves 5 cm3 of CH4 and 5 cm3 of C2H4? A 10 cm3 B 15 cm3 C 20 cm3 D 25 cm3 15 Hydrocarbon 13 Which of the following statements is not caused by the delocalisation of pi electrons in benzene? A The C-C bond lengths in benzene are identical. B Each carbon atom in benzene undergoes sp2 hybridisation. C Benzene tends to undergo substitution rather than addition reactions. D The enthalpy of hydrogenation of benzene is higher than that of cyclohexene. 15 Hydrocarbon 14 Which reagent and conditions are used to bring about the reaction shown? A Cl2 in the dark B Cl2 with AlCl3 C Cl2 with ultraviolet light D concentrated HCl catalysed by ZnCl2 heated under reflux

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 15 Hydrocarbon 15 A hydrocarbon X contains 85.7% carbon and 14.3% of hydrogen by mass. X reacts with hydrogen in the presence of nickel catalyst. The structural formula of X could be. A CH3CH2CH2CH2CH2CH3 B CH3CH=CHCH2CH2CH3 C D 16 Haloalkanes 16 Which of the following compounds react with aqueous sodium hydroxide via SN1 mechanism? A CH3CH2CH2CH2Cl B C D 16 Haloalkanes 17 A liquid L, C7H6Cl2, gives a white precipitate when shaken for some time with cold ethanolic silver nitrate. What could be L? A I and IV only B II and III only C I, II and III only D III and IV only

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 16 Haloalkanes 18 The carbon-halogen bond in chloromethane is more polarised than that in bromomethane. Why? A The C-Cl bond is shorter than the C-Br bond. B The C-Cl bond is stronger than the C-Br bond. C Cl is more electronegative than Br. D The electron affinity of Cl is higher than Br. 16 Haloalkanes 19 Fenoprofen is an anti-arthritic agent. Which of the following could be part of a sequence for synthesising Fenoprofen? Fenoprofen A B C D 16 Haloalkanes 20 It is estimated that for every chlorine atom formed from a fluorohaloalkane in the stratosphere, one hundred thousand ozone atoms may be destroyed. Which of the following statements provides an explanation for this? A They achieve high activation energy by absorbing ultraviolet light. B They eliminate oxygen from ozone - oxygen equilibrium. C They initiate ionisation of oxygen molecule D They are regenerated in a chain reaction with ozone 17 Hydroxy Compounds 21 Which reagent will react with ethanol and phenol? A Bromine water B Potassium hydroxide C Iron(III) chloride D Propanoyl chloride

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 17 Hydroxy Compounds 22 Which of the following is most susceptible to electrophilic substitution? A Cyclohexanol B Cyclohexenol C Phenol D 2-Nitrophenol 17 Hydroxy Compounds 23 Which of the following pairs of compounds can react to produce a compound with the following structural formula? A I and IV only B II and III only C I, II and III only D I only 17 Hydroxy Compounds 24 When phosphorus pentachloride is added to the organic compound X, hydrogen chloride fumes will be released. If substance X is heated with acidified potassium dichromate(VI) solution, the solution changes colour to green, Compound X is most probably A B C D

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 17 Hydroxy Compounds 25 The scheme below shows the formation of compound Z from propan-2-ol. Which of the following compounds could be X, Y, and Z? X Y Z A PCl5 B PCl5 C SOCl2 D Cl2 17 Hydroxy Compounds 26 Which reagent will react with ethanol and phenol? A Bromine water B Potassium hydroxide C Iron(III) chloride D Propanoyl chloride 27 18 Carbonyl Compounds A compound reduces Fehling’s Solution and form triiodomethane. The compound could be A ethanol B butanal C 3-hydroxybutanal D propyl methanoate 18 Carbonyl Compounds 28 Which alkene will form a ketone when heated with acidified KMnO4 solution? A CH3CH2CH=CH2 B CH3CH=CHCH2CH3 C CH3CH2CH=CHCH2CH3 D (CH3)2=CHCH3

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 18 Carbonyl Compounds 29 When phosphorus pentachloride is added to the organic compound X, hydrogen chloride fumes will be released. If substance X is heated with acidified potassium dichromate(VI) solution, the solution changes colour to green, Compound X is most probably A B C D 18 Carbonyl Compounds 30 Given the following organic compounds P and Q. The following methods can be used to differentiate organic compounds P and Q except A Adding Tollens reagent. B Warm with Fehling’s solution. C Heating under reflux in alkaline iodine. D Heating under reflux in acidified potassium manganate(VII) solution.

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 18 Carbonyl Compounds 31 Given the following organic compounds P and Q. The following methods can be used to differentiate organic compounds P and Q except A Adding Tollens reagent. B Warm with Fehling’s solution. C Heating under reflux in alkaline iodine. D Heating under reflux in acidified potassium manganate(VII) solution. 19 Carboxylic Acids and their Derivatives 32 A manufacturer wishes to make methyl salicylate, the aromatic liniment of oil of wintergreen, from salicylic acid. How is this esterification of salicylic acid best achieved? A mixing it with cold ethanoyl chloride B warming it with anhydrous methanol C heating it under reflux with methanol and a little concentrated sulphuric acid D heating it under reflux with ethanoic acid and a little concentrated sulphuric acid 19 Carboxylic Acids and their Derivatives 33 Propanoic acid is heated with concentrated ammonia to produce compound X. Which statement is true about compound X. A Compound X is basic. B Compound X reacts with ethanoyl chloride to form N-ethylpropanamide. C Compound X react with cold nitrous acid. D Compound X undergoes esterification with alcohol in concentrated sulphuric acid. 19 Carboxylic Acids and their Derivatives 34 2-chlorobutanoic acid is more acidic than 4-chlorobutanoic acid because A it has a higher solubility in water. B its carboxylate anion is less stable. C it forms a stronger conjugate base. D of the more effective inductive effect of Cl atom towards the carboxyl group.

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 19 Carboxylic Acids and their Derivatives 35 The structural formula of isomer X and Y are shown below. X Y Which statements is true about X and Y? A X and Y undergo reduction reaction. B X and Y have the same boiling points. C X is produced when Y is hydrolysed. D X and Y form the same amides when they react with ammonia. 19 Carboxylic Acids and their Derivatives 36 The pKa values for four organic species at 25 °C are given in the table below. Species Structural formula pKa Benzoic acid 4.20 4-methylbenzoic acid 4.26 Anilinium ion 4.58 4-methylanilinium ion 5.10 Based on the data given, which statement is true? A Benzoic acid is the most stable species B 4-methylanilinium ion is more stable than 4-methylbenzoic acid C 4-methylaniline is a weaker base than aniline D 4-methylanilinium ion is the most acidic species 19 Carboxylic Acids and their Derivatives 37 Compound M reacts with concentrated ammonia to produce N. When N is treated with lithium tetrahydridoaluminate in ether, followed by acid hydrolysis, propanamine is obtained. M could be A CH3CH2CH2Cl B CH3COOCH3 C CH3CH2COCl D CH3CH2CH2OH

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 19 Carboxylic Acids and their Derivatives 38 Citric acid has the following structural formula. Which of the following is not true of citric acid? A It decolourises acidified KMnO4. B It reacts with lithium tetrahydridoaluminate to produce C It is not optically active. D It is a solid at room conditions. 19 Carboxylic Acids and their Derivatives 39 Which reaction represents a substitution reaction which occurs through electrophilic mechanism? A B C D 20 Amine, Amino Acids and Proteins Amine 40 An amine compound is formed according to the following reaction. What are the reagents required in step I and step II of the above reactions? Step I Step II A Ammonia gas Hydrogen gas B Ammonia gas Hydrogen cyanide C Potassium cyanide Lithium tetrahydridoaluminate D Aqueous ammonia gas Sodium hydroxide in ethanol

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 19 Carboxylic Acids and their Derivatives (Amide) 41 The amino acids aspartic acid and glutamic acid can react with each other to form amide inkages. What is the maximum number of different compounds, each containing one amide linkage, that can be formed from one molecule of aspartic acid and one molecule of glutamic acid? A 1 B 2 C 4 D 6 19 Carboxylic Acids and their Derivatives 42 Which compound releases nitrogen gas when it reacts with nitrous acid? A CH3C(CH2)2CH2NH2 B CH3CH2NHC(CH3)3 C CH3CH2CH2CONH2 D (CH3CH2)3N 19 Carboxylic Acids and their Derivatives 43 A chemist produced methyl salicylate from salicylic acid, which is used in the production of the production of wintergreen oil. In the esterification above, X represents one of the following processes. X is the A heating with dry methanol. B addition of cold ethanoyl chloride and concentrated sulphuric acid. C heating under reflux with methanol and concentrated sulphuric acid. D heating under reflux with ethanoic acid and concentrated sulphuric acid.

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 19 Carboxylic Acids and their Derivatives 44 Which compound forms a white precipitate when heated with an aqueous solution of sodium hydroxide followed by acidification? A B C D 19 Carboxylic Acids and their Derivatives 45 An organic compound X, which fumes in air, reacts with an alkaline solution of phenol to produce compound Y. What could X and Y be? X Y A CH3COCl CH3COOC6H5 B CH3COCl C6H5COOCH3 C CH3CH2Cl CH3COOC6H5 D CH3CH2Cl C6H5COOCH2CH3 19 Carboxylic Acids and their Derivatives 46 A chemist produced methyl salicylate from salicylic acid, which is used in the production of the production of wintergreen oil. In the esterification above, X represents one of the following processes. X is the A heating with dry methanol. B addition of cold ethanoyl chloride and concentrated sulphuric acid. C heating under reflux with methanol and concentrated sulphuric acid. D heating under reflux with ethanoic acid and concentrated sulphuric acid.

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 19 Carboxylic Acids and their Derivatives 47 Vitamin C has the following structure. How many chiral centres are there in one molecule? A 1 B 2 C 3 D 4 19 Carboxylic Acids and their Derivatives 48 The pKa values for four organic species at 25 °C are given in the table below Species Structural formula pKa Benzoic acid 4.20 4-methylbenzoic acid 4.26 Anilinium ion 4.58 4-methylanilinium ion 5.10 Based on the data given, which statement is true? A Benzoic acid is the most stable species B 4-methylanilinium ion is more stable than 4-methylbenzoic acid C 4-methylaniline is a weaker base than aniline D 4-methylanilinium ion is the most acidic species 19 Carboxylic Acids and their Derivatives 49 Propanoic acid is heated with concentrated ammonia to produce compound X. Which statement is true about compound X. A Compound X is basic. B Compound X reacts with ethanoyl chloride to form N-ethylpropanamide. C Compound X react with cold nitrous acid. D Compound X undergoes esterification with alcohol in concentrated sulphuric acid.

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 19 Carboxylic Acids and their Derivatives 50 Citric acid has the following structural formula. Which of the following is not true of citric acid? A It decolourises acidified KMnO4. B It reacts with lithium tetrahydridoaluminate to produce C It is not optically active. D It is a solid at room conditions. 19 Carboxylic Acids and their Derivatives 51 Compound M reacts with concentrated ammonia to produce N. When N is treated with lithium tetrahydridoaluminate in ether, followed by acid hydrolysis, propanamine is obtained. M could be A CH3CH2CH2Cl B CH3COOCH3 C CH3CH2COCl D CH3CH2CH2OH 20 Amine, Amino Acids and Proteins 52 Nylon 6,6 is a condensation polymer derived from a diamine, and a dioic acid, Which of the following compound reacting with hexane-1,6-diamine, would provide the most rapid method of preparing the polymer? A diethyl hexanedioate B hexane-1,6-diol C hexanedioic acid D hexanedioyl chloride

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 20 Amine, Amino Acids and Proteins 53 Fructose is an example of a monosaccharide. Its structural formula is shown below. Which statement about fructose is correct? A It is insoluble in water. B It has two chiral carbons. C It reacts with an aqueous solution of sodium carbonate. D It decolourises an acidified solution of potassium manganate (VII). 20 Amine, Amino Acids and Proteins 54 The gases given off when a compound reacts with several reagents are as follows. Reagent Gas NaHCO3 (aq) CO2 NaNO2/HCl (aq) N2 PCl5 HCl What is the compound? A CH3NHCH2COOH B H2NCH2CH2COOH C D 20 Amine, Amino Acids and Proteins 55 Which statement is true about HOCH2COOH and H2NCH2COOH? A HOCH2COOH and H2NCH2COOH react with nitrous acid. B HOCH2COOH and H2NCH2COOH acts as buffer solutions. C HOCH2COOH and H2NCH2COOH react with phosphorous pentachloride. D HOCH2COOH and H2NCH2COOH form salts when react with hydrochloric acid.

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 20 Amine, Amino Acids and Proteins 56 Which compound releases nitrogen gas when it reacts with nitrous acid? A CH3C(CH2)2CH2NH2 B CH3CH2NHC(CH3)3 C CH3CH2CH2CONH2 D (CH3CH2)3N 21 Polymers 57 Polychloroethene is manufactured by a free radical process where chloroethene is heated under high pressure with benzoyl peroxide, (C6H5COO)2. Which of the following is the propagating step in this reaction mechanism? A B C D 21 Polymers 58 Pentaerythritol is an intermediate used in the manufacture of paint and has the structural formula as follows: Which statement(s) is/are true of pentaerythritol? I It is a monomer for a cross-link polymer II It reacts with SOCl2 III It can be dehydrated to an alkene A I only B I and II only C II and III only D I, II and III

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 21 Polymers 59 The repeating unit of a polymer is shown below. Which of the following statements is not true of the polymer? A It is elastic. B It is thermally stable. C It can be vulcanised. D Its monomers are 21 Polymers 60 Polychloroethene is manufactured by a free radical process where chloroethene is heated under high pressure with benzoyl peroxide, (C6H5COO)2. Which of the following is the propagating step in this reaction mechanism? A B C D

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin Section B 1 (a) A series of reactions, starting from compound P, C4 H9 Br, is shown below. Q can form geometrical isomerism. (i) Write the structural formulae of compounds P, Q, R, S and T in the boxes provided. [5 marks] (ii) Write the equation of compound S reacts with Brady’s Reagent. ……………………………………………………………………………. ……………………………………………………………………………. [2 marks]

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 2 Crotyl alcohol, , is a colourless liquid which is used as a solvent (a) Explain the stereoisomer present in crotyl alcohol and draw the isomers stated. ……………………………………………………………………………. ……………………………………………………………………………. Isomers present : [3 marks] (b) In the boxes below, draw the structural formula of the organic compounds formed when crotyl alcohol is reacted separately with each reagent under suitable conditions. (i) Hydrogen gas catalysed by platinum (ii) Phosphorous pentachloride (iii) Bromine water (iv) hot acidified potassium manganate (VII) [4 marks]

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 3 (a) Alkene undergoes additional reaction according to Markovnikoff’s rule. (i) State Markovnikoff’s rule. ……………………………………………………………………………..… ……………………………………………………………..…………………. [1 mark] (ii) Draw the structural formula of the major product of these alkenes reaction. [3 marks] (b) 2-methylbut-1-ene can be prepared from alcohol using excess concentrated sulphuric acid at 180C. (i) Name the type of reaction occur for the preparation of 2-methylbut-1-ene from alcohol. …………………………………………………………………… [1 mark] (ii) Name two possible alcohols that can be used to prepare 2-methylbut-1-ene. ……………………………………………………………….. ………………………………………………………………… …………………………………………………………………. [2 marks]

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 4 (a) Freon-12, CF2Cl2, is an example of chlorofluorocarbons, CFCs, are small alkane molecules in which some of the hydrogen atoms have been replaced by atoms of chlorine and fluorine. (i) Give the IUPAC name for one of the CFC available in industries. ……………………………………………………………………..………… ……………………………………………………………………………….. [1 mark] (ii) State two uses of CFC and state one of the properties of CFCs causes them to be useful. Uses Properties [2 marks] (b) Presence of CFC is well-concerned due to its effect on the ozone, O3, in stratosphere layer. (i) State one function of ozone in stratosphere layer ……………………………………………………………………………….. ……………………………………………………………………………….. [1 mark] (ii) State the reaction and proposed the mechanism of the depletion of ozone layer by CFC. [4 marks]

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 5 A colour dye, Y, can be synthesis using 4-nitroaniline from the following reaction scheme (i) Fill in the blank for reagent A, compound X and colour dye Y. [3 marks] (ii) State the type of reaction between compound X and aniline to form Y . …………………………………………………………………..………….. ………………………………………………………………………………. [1 mark] (iii) Compare the basicity between aniline, 4-nitroaniline and ethylamine. ………………………………………………………………………………... ………………………………………………………………………………... ………………………………………………………………………………... ………………………………………………………………………………... [4 marks]

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 6 Compound Z which can be obtained from the reaction of an amine and a phenol under suitable conditions has the following structure: (i) Draw the structural formula of the amine and the phenol used to make compound Z. [2 marks] (ii) Write the equations with reagent and conditions to convert the amine and the phenol into compound Z. [3 marks] (iii) Give a chemical test to differentiate between compound Z and the amine. [3 marks]

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 7 (a) The reaction scheme for the preparation of 3-nitrobenzoic acid from benzene shown below Identify reagents X, Y and Z Reagent X: …………………………………………………. Reagent Y: …………………………………………………. Reagent Z: …………………………………………………. [3 marks] (b) Compounds K and L, of C5H11Cl are secondary haloalkanes. Both K and L are optically active isomers. K undergoes an elimination reaction to produce two isomeric alkenes, M and N. M shows cis-trans isomerism. Draw the structure of K, L, M and N. K L M N [4 marks]

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 8 Butan-1-ol can be oxidised by acidified potassium dichromate (VI) using two different methods. In the first method, butan-1-ol is added dropwise to acidified potassium dichromate (VI) and the product is distilled off immediately. (a) Using the symbol [O] for the oxidising agent, write an equation for the oxidation of butan-1-ol, show clearly the structure of the product. State what colour change you would observe. Equation: ………………………..………………………………………… Colour change: …………………………………………………………….. [2 marks] (b) Butan-1-ol and butan-2-ol give different products on oxidation by this first method.By stating a reagent and the observation with each compound, give a simple test to distinguish between these two oxidation products. Reagent: …………………………………………………………………… Observation with oxidation product of butan-1-ol: ……………………………………………………………………………… ……………………………………………………………………………… Observation with oxidation product of butan-2-ol: …………………………………………………………………………….. ……………………………………………………………………………… [6 marks]

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin Section C 17 Hydroxyl Compound 1 (a) The table below list the pKa value for three hydroxyl compounds in aqueous solution at 298 K. Name of compound Formula pKa Cyclohexanol 18 Phenol 10 4-nitrophenol 9.2 (i) Arrange the three compounds above in the order of decreasing acidity and explain your answer [6 marks] (ii) State a chemical test used to distinguish between cyclohexanol and phenol [3 marks] (b) 2,3-dimethylpentan-3-ol dehydrated according to Saytzeff's rule using suitable reagent and condition. By drawing the structure of the products formed, explain how the yield of the products varies according to the rules [6 marks] 14 Introduction to Organic Chemistry (Alkanes) 2 Ester A, C9H10O2 when subjected to hydrolysis, compound B and C are produced. When water is added to compound B, an acidic solution, D is formed. Compound D undergoes reduction and form compound E. Compound E forms yellow precipitate with iodine in alkali solution. Compound C decolourises Bromine water and form white precipitate, F. Compound C also can be oxidized to G, (a) Identify the structures A, B, C, D, E, and F [6 marks] (b) Write the equations involved. [7 marks] (c) Which compound is more reactive towards nucleophilic attack, compound B or chloroalkanes? Explain. [2 marks]

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 19 Carboxylic Acids and their Derivatives 3 (a) Benzocaine is a local anesthetic used by pharmacy which can be synthesis from 4-aminobenzoic acid. Equation for the formation of benzocaine is given in the equation below Starting from benzene, propose a reaction schemes to synthesis 4- aminobenzoic acid. Include also the reagent and condition for each step proposed [7 marks] (b) Benzene, toluene and nitrobenzene each undergoes acylation reaction in the presence of aluminium trichloride. (i) Describe the mechanism of acylation in nitrobenzene [5 marks] (ii) Arrange the rate of acylation in benzene, toluene and nitrobenzene. Explain your answer. [3 marks] 21 Polymers 4 (a) Polypropene is a thermoplastic which can be produced using a Ziegler-Natta catalyst. The polymer formed is stereoregular with a section of the polymer chain shown below. (i) What is a Ziegler-Natta catalyst? [1 mark] (ii) State two properties of polypropene produced using a Ziegler-Natta catalyst, and give one use of polypropene. [3 marks] (iii) Draw a structure of the repeating unit of the polymer. [1 mark] (b) The structure of a section of a polymer is shown below. -CO-(CH2)4-CO-NH-(CH2)6-NH-CO-(CH2)4-CO-NH-(CH2)6-NH- (i) Name the polymer and its monomers. [3 marks] (ii) Write the reaction scheme for the preparation of these monomers starting from cyclohexane-l,2-diol. [5 marks] (iii) State one property of the polymer and give one of its uses. [2 marks]

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 14 Introduction to Organic Chemistry 5 (a) The empirical formula of compounds P and Q is CH. Compound P has three and two π bonds, while compound Q has 12 σ and three π bonds. (i) Draw the structural formulae of compound P and Q, and state the class of each compound [4 marks] (ii) Show the delocalisation of electron in compound Q. [2 marks] (b) A hydroxy compound R, with a molecular formula C4H10O is optically active. R reacts with alkaline iodine to produce a yellow precipitate. (i) Deduce the structure of R and craw its optical isomers. Write the equation for the reaction involved. [6 marks] (ii) State the reagent and reaction condition for the synthesis of R starting from the alkene of your choice. [3 marks] 15 Hydrocarbon 6 Both benzene and phenol undergo nitration at 55C to form nitrated products (a) Write the chemical equation for both reactions and compare their reactivity. Draw the mechanism of nitration of phenol [12 marks] (b) Describe the solubility of benzene and phenol in water. [3 marks] 17 Hydroxyl Compound 7 Methanol and compound S are alcohols. The structural formula of compound S is shows below (a) Compare the acidity of compound Q with methanol. Explain your answer. [4 marks] (b) Suggest a chemical test to differentiate compound from methanol. State the observation and write the reaction equation. [3 marks] (c) Write a synthetic pathway to show how compound Q can be prepared from phenol. [8 marks]

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 19 Carboxylic Acids and their Derivatives 8 Ester A, C9H10O2 when subjected to hydrolysis, compound B and C are produced. When water is added to compound B, an acidic solution, D is formed. Compound D undergoes reduction and form compound E. E forms yellow precipitate with iodine in alkali solution. Compound C decolourises Bromine water and form white precipitate, F. Compound C also can be oxidised to G, (a) Identify the structures A, B, C, D, E, and F. [6 marks] (b) Write the equations involved. [7 marks] (c) Which compound is more reactive towards nucleophilic attack, compound B or chloroalkanes? Explain. [2 marks] 16 Haloalkanes 9 (a) The reaction-energy profile for the reaction between haloalkane X with molecular formula C4H9Br and solution of alcoholic potassium cyanide is shown below. (i) Name and describe the mechanism of the reaction. [6 marks] (b) Haloalkane can be converted to useful organic compound in condensation polymerisation such as alcohol. Carboxylic acid and amine. Kelvar, a synthethic fibre used in making tyre cords and bulletproof vests has following structure (i) Draw structural formulae of the repeating unit and the monomers for Kevlar. [3 marks] (ii) Explain how you can prepare the monomers of Kelvar starting from benzene. [6 marks]

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 18 Carbonyl Compounds 10 (a) Suggest how 2-methyl-3-phenylpropanoic acid could be prepared from a secondary alcohol. Give the reagents involved and the intermediate compounds formed. (b) Glucose is a monosaccharide which acts as reducing sugar and can be used to make sorbitol, a sweetener which is used by diabetics to replace glucose. Sorbitol can be prepared by reduction of glucose. (i) Write an equation for the reaction involved in the preparation of Sorbitol from glucose. [3 marks] (ii) Define the term ‘disaccharide’. [1 mark] (iii) Using suitable chemical equation, explain how two glucoses react to form sucrose. [4 marks] 14 Introduction to Organic Chemistry 11 Two gaseous hydrocarbon, A and B has the same composition by mass; carbon by 85.7% and hydrogen 14.3%. When 0.020 mol of gas A and 0.020 mol of gas B are both burned separately, the products of the combustion are passed through anhydrous calcium chloride and then through potassium hydroxide solution. The masses of anhydrous calcium chloride and potassium hydroxide solution increase by 1.08g and 2.64g respectively. When mixed with bromine gas undersunlight, both gas A and B decolourised the brown vapour. However, only gas A decolourised cold dilute alkaline potassium manganate (VII) while gas B will not. (a) Calculate the empirical formula for both gas A and gas B. [2 marks] (b) Calculate the molecular formula for both gas A and gas B. [5 marks] (c) Explain the molecular structure of gas A and gas B. [8 marks] 12 14 Introduction to Organic Chemistry (a) An optical active compound J, with the molecular formula C4H9Cl, undergoes hydrolysis to form compound K. When compound K is oxidised using a strong oxidising agent, compound L is produced. As J react with magnesium and then react with compound L under acidic condition, compound M is formed. Draw all strucutral isomers of C4H9Cl, hence explain the structure of J, K, L and M. [11 marks] (b) Determine the isomer of J which reacts with ethanolic potassium hydroxide solution to form only one organic compound. Give a reason for your answer. [4 marks]

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin 13 19 Carboxylic Acids and their Derivatives (a) Outline the reaction scheme of how to produce N-benzylethanamide from benzene Include the reagents and conditions required in the proposed scheme [7 marks] (b) State the products produced when N-benzylethanamide react with the following reagents and conditions (i) boiled hydrochloric acid [2 marks] (ii) boiled sodium hydroxide [2 marks] (iii) lithium tetrahydridoaluminate in dry ether ; followed by acidic solution. [1 mark] (c) Identify the reagents necessary for the following transformation: [3 marks]

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin Answer Scheme

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin Answer Scheme (SECTION A) 1 C 31 C 2 A 32 C 3 D 33 C 4 A 34 D 5 A 35 A 6 D 36 B 7 A 37 C 8 B 38 A 9 A 39 B 10 A 40 C 11 D 41 C 12 D 42 A 13 B 43 C 14 B 44 D 15 C 45 A 16 D 46 C 17 B 47 A 18 C 48 B 19 A 49 C 20 D 50 A 21 D 51 C 22 C 52 D 23 A 53 D 24 B 54 B 25 C 55 C 26 D 56 A 27 C 57 D 28 D 58 B 29 B 59 B 30 C 60 D

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin Answer Scheme (SECTION B) Q 1. 16 Haloalkanes (i) P is 1 Q is 1 R is 1 S is 1 T is 1 (ii) 2 Product –[1] Equation- [1] Total 7 Q 2. 17 Hydroxyl compounds a) Geometrical isomer present - each C in C=C is surrounded by 2 different atoms / group of atoms [1] cis – isomer trans - isomer (Structures [1] label cis trans [1] ) [4] Total 7

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin Q3. 15 Hydrocarbons Total 7 Q 4. 16 Haloalkanes Total 8

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin Q5: 20 Amines, Amino Acids and Proteins A : conc. HNO3 in conc. H2SO4 X : Y : ii) electrophilic aromatic substitution reaction iii) basicity increase : 4-nitroaniline < aniline < ethylamine - alkyl group in ethylamine is electron donating group; stabilising aminium ion formed - phenyl is electron withdrawing group, causing anilinium ion formed to be less stable - NO2 caused inductive effect / further destabilised the anilinium ion formed 1 1 1 1 1 1 1 1 Total 8 Q6: 20 Amines, Amino Acids and Proteins (i) 1 1 (ii) 3 (iii) - React with nitrous acid, HNO2 with Z and amine separately and heated to 700C 1 - Observation: Effervescence occurs (N2 released) for amine. No observable changes for Z 1 - Equation: 1 Total 8

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin Q7: 14 Introduction to Organic Chemistry Reagent X: CH3CH2Cl in AlCl3 1 Reagent Y: Hot acidified KMnO4 1 Reagent Z: HNO3 and H2SO4; Heat 1 1 1 1 1 Total 7 Q8: 18 Carbonyl Compounds a) CH3CH2CH2CH2OH → CH3CH2CH2CHO 1 Orange to green 1 b) Tollen’s reagent 2 Silver mirror formed 2 No observable change 2 Total 8

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin Answer Scheme (SECTION C) ANSWER Q 1 - 17 Hydroxyl Compound 18. a) i) m1 : Acidity decrease according to order [1] m2 : cyclohexane is electron-donating / positive inductive [1] m3 : caused alkoxide more readily to accept proton @ cause equilibrium shift to left [1] m4 : benzene is electron withdrawring / negative inductive [1] m5 : caused phenol more readily to donate proton @ caused equilibrium shift to right [1] m6 : NO2 gives negative inductive / electron withdrawing / stabilised phenoxide ion formed [1] 6 ii) Alternative 1 : Reagent : acidified KMnO4 / H+ [1] Observation : purple colour decolourised by cyclohexanol but not by phenol [1] Equation : [1] Alternative 2 : Reagent : bromine water [1] Observation : brown colour decolourised and white precipitate is formed when added to phenol [1] Equation : bromination of phenol [1] 3 b) m1 : Saytzeff rule : in elimination of H-X or H2O, H is preferable to eliminate from neighbouring C with less H [1] m2 : reagent : alumina / conc. H2O under heating [1] m3 : Structure of 2,3-dimethylpentan-3-ol [1] 6

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin m4 ; m5 ; m6 - 3 products of dehydration [3] Total: 15

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin Q2 - 14 Introduction to Organic Chemistry (Alkanes) (a) Structures of A is 1 B is 1 C is 1 D is 1 E is 1 F is 1 (b) 1 1 2 3 (c) - B is more reactive [1] - the electron withdrawing effect at the C=O group causes the carbonyl atom to be more partially positive. [1] 2 Total 15

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin Q 3 - 19 Carboxylic Acids and their Derivatives Total 15

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin Q 4 - 21 Polymers Total 15

CONFIDENTIAL* Module ‘A’cceleration STPM Johor Bahru S3 2022/2023 SULIT* Goh San San, Nur Fathin Suhana bt Ayob, Wong Minh Chjiat Isabelle, Chew Chin Kuen, Mohamad Rashidi bin Anang & Noreza bt Salleh Hudin Q5 - 14 Introduction to Organic Chemistry (a) (i) 4 (ii) 2 (b) (i) 6 (ii) Mix 1-butene with steam and pss over a catalyst consisting of solid silicon dioxide coated with phosphoric (V) acid at 300oC and 70 atm. Total 15