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Organic Chem MCQ Revision For 2012 CT 1

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2010 Organic Chemistry MCQ

1 After heating acidified potassium permanganate with the molecule below, how many sp2 carbons are there present in the resultant compound?
CH3 O

HO

A 6

B 9

C 10

OH

D 11 ACJC Prelim 2010

2 How many stereoisomers are there in the compound shown?

A 2

B 4 C 6 D 8 ACJC Prelim 2010

3 When excess BrCl is added to the methylbenzene in the presence of UV light, which organic compound will be produced in the smallest proportion? A
CH2Br

CHBr2

CH2

CH2Cl

CH2

ACJC Prelim 2010

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4 When the following compound shown below is oxidized with alkaline potassium manganate(VII), one of the products include
CH2 ClHClCH C 2 2CH2

CH3CO H2
HOCH CH2 ClH C 2CH22 O
HOCH CH2 ClH C 2CH 22

CH3CO H2
CH2 ClHClCH C 2 2CH 2 O

CO2 H

ClH2OOCCH CH2C 2

CO2 H

O H

ACJC Prelim 2010

5 Which one of the following alcohols will give the largest number of alkenes when treated with concentrated sulphuric acid? A C

ACJC Prelim 2010

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6 A 1,2-hydride shift is common in producing a more stable carbocation. For example, when removing the halogen from CH3CH2CH2Cl, a hydride shift will take place to produce a more stable carbocation.
H H C H H C H H C
+

H
Hydride shift

H C H
+

C H

C H

What will be the most likely product formed when (CH3)2CHCHClCH3 is added to AlCl3 and then the mixture is added to benzene? (Ph represents benzene) A CH3CH2CH2CH2CH2Ph C (CH3)2CHCH(Ph)CH3 B (CH3)2CHCH2CH2Ph D (CH3)2C(Ph)CH2CH3 ACJC Prelim 2010 7 Ethanal reacts with CN from HCN in the presence of a weak base as shown below
H

O CH3 C H

OH

HCN

CH3 C CN

In a similar reaction, CH2COCH3 ions are generated when CH3COCH3 reacts with a strong base. Which one of following compounds is the product when ethanal reacts with CH2COCH3? A CH3CH(OH)CH2COCH3 C (CH3)2C(CHO)CH2OH B CH3)2C(OH)CH2CHO D (CH3)2C(OH)COCH3 ACJC Prelim 2010 8 Phenol has a pKa of 5.7. Which one of the following has a lower pKa value? A (CH3)3CCOOH C 2,4,6-trimethylphenol

ACJC Prelim 2010

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9 A liquid P is sparingly soluble in water but dissolves readily in cold hydrochloric acid. Evaporation of this solution yields a crystalline solid. Which of the following could be P? A C6H5COCH3 C C6H5NH2 B C6H5CN D C6H5OH ACJC Prelim 2010 10 Acetaminophen is a drug used in headache remedies. It has the structure

H HO N

CH3 C O

Which of the following equations gives the best method for its synthesis?
HO Cl

A B C D
HO NH2

+
+

CH3 H2NC O

H HO N
H

CH3 C
CH3 C CH3 C O O

+
+

HCl

CH3COCl

HO H

HCl

HO

NHCOCl

CH3Cl

HO

+
O

Cl2

H HO NHNH2

CH3 C

ACJC Prelim 2010 11 Some chlorobutanes were separately treated with hot ethanolic sodium hydroxide. Two of these gave the same hydrocarbon, C4H6. From which pair of chlorobutanes was this hydrocarbon obtained? A CH3CH2CH2CH2Cl and CH3CH2CCl2CH3 B CH3CH2CH2CH2Cl and ClCH2CH2CH2CH2Cl C CH3CHClCHClCH3 and ClCH2CH2CH2CH2Cl D CH3CH2CH2CH2Cl and CH3CH2CH2CHCl2. CJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

+ CH3CHO

HO

+ NH3

12 In recent years, a number of athletes have been banned from sports because of their illegal use of synthetic testosterone.
CH3 OH CH3

Testosterone is first refluxed with concentrated KMnO4, and the product is then reacted with HCN in trace of NaOH. How many chiral centres are present in the final product? A 6 B 7 C 8 D 9 AJC Prelim 2010 13 Use of the Data Booklet is relevant to this question. The bond energy of the CH bond (438 kJ mol1) in CH4 is typically stronger than most other aliphatic CH bonds. This has an effect on the first step of the propagation stage of the reaction between CH4 and the halogen. CH4 + X CH3 + HX where X = F, Cl, Br or I On the basis of bond energies, which statement about the reaction between CH4 and the halogen is incorrect? A Bromine and iodine essentially do not react with methane. B Fluorine is so reactive that neither UV light or heat is needed. C The order of halogen reactivity is due to the decreasing strength of the HX bond. D The H for the first propagation step is more endothermic for the chlorination of C2H6. AJC Prelim 2010 14 Which reagent reacts with a secondary alcohol, under suitable conditions, to give an organic product with the same number of oxygen atoms as the alcohol? A Al2O3 B CH3CO2H C K2Cr2O7 D PCl5 AJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

testosterone

15 Deuterium, D, is a heavy isotope of hydrogen. Deuteriobenzene is reacted with a mixture of nitric acid and sulfuric acid under controlled conditions, so that only mononitration takes place. Assuming that the carbondeuterium bond is broken as easily as a carbonhydrogen bond, which proportion of the nitrated products will be 3nitrodeuteriobenzene?
D D

NO2 deuteriobenzene

AJC Prelim 2010 16 Four drops of 1chlorobutane, 1bromobutane, 1iodobutane were put separately into three testtubes containing 1.0 cm3 of aqueous silver nitrate at 60 C. A hydrolysis reaction occurred. (R represents the butane chain C4H9 and X the halogen atom) H2O(l) + RX(l) + Ag+(aq) ROH(aq) + AgX(s) + H+(aq) The rate of formation of cloudiness in the tubes was in the order RCl < RBr < RI. What helps to explain this observation? A The bond energy of RX decreases from RCl to RI. B The ionisation energy of the halogen decreases from Cl to I. C The RX bond polarity decreases from RCl to RI. The solubility of AgX(s) decreases from AgCl to AgI. AJC Prelim 2010 17 In what way is propene similar to propane? A Both can be obtained by the dehydration of alcohols. B Both can react with chlorine under suitable conditions. C Both can be hydrogenated using a suitable catalyst. D Both can undergo polymerisation under suitable conditions. CJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

A 16%

3-nitrodeuteriobenzene

B 20%

C 33%

D 45%

18 The compound T, CH3COCH2CHO, was reacted in separate experiments with: (i) alkaline aqueous iodine; (ii) 2,4dinitrophenylhydrazine; (iii) Tollens reagent [Ag(NH3)2]+(aq); (iv) lithium aluminium hydride in dry ether. One mole of T could A form two moles of CHI3 in (i). B react with two moles of 2,4dinitrophenylhydrazine in (ii). C form one mole of CH3COCH2CH2OH and two moles of Ag in (iii). D form a product in (iv) which further reacts with Na to produce two moles of H2 gas. AJC Prelim 2010 19 Aspartame is widely used as a sweetener in canned drinks.
H2N CHCONHCHCO2CH3 HO2CCH2 CH2 Aspartame

Which compound would be a product of its hydrolysis with aqueous NaOH? A CH3CO2
CO2H H2NCH

B C D

CH2CO2H

NH2 CH2CO2

CH2CH2NH2

CH2CHNHCOCH CO2

AJC Prelim 2010

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20 Dopamine is a drug used in the treatment of Parkinsons disease. Which of the following statements about this compound is correct? A It can dissolve in aqueous sodium hydroxide but not hydrochloric acid.
HO CH2I

AJC Prelim 2010 21 A sample of a peptide of an unknown sequence was tested with enzymes. The sequences of the smaller peptides produced were LeuSer LysLeu LeuAlaPheGln SerTyrLeu What was the sequence of the original peptide? A SerTyrLeuAlaPheGlnLysLeu B LysLeuAlaPheGlnSerTyrLeu C LysLeuSerTyrLeuAlaPheGln D LeuSerTyrLeuAlaPheGlnLys AJC Prelim 2010 22 Which of the following about the amino acid, methionine, is true? A complete combustion of ethene in air B heating methanal with LiAlH4 in dry ether C mixing methane with chlorine gas in the presence of UV light D heating bromoethane under reflux with alcoholic potassium hydroxide CJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

HO B It can be synthesised from C It decolourises aqueous bromine only in the presence of light. D Three moles of CH3COOH will react with one mole of Dopamine.

 23 The following shows the time taken for appearance of precipitate after adding aqueous AgNO3 to four halogen derivatives separately. Halogen Derivative Time for precipitate to appear Chlorobenzene No precipitate 2-chlorobutane 10 minutes 2-bromobutane 2 minutes 2-iodobutane Instantaneous Which of the following would be the best explanation for the observation? A The lattice energy becomes more exothermic from AgCl to AgI. B The ease of electron cloud distortion decreases from chlorobenzene to 2-iodobutane. C The carbon-halogen bond strength decreases from chlorobenzene to 2-iodobutane. D The carbon-halogen bond length decreases from 2-chlorobutane to 2-iodobutane. CJC Prelim 2010 24 Tyrosol is a naturally occurring oxidant found in olive oil.
HO OH

Tyrosol

Which statement about Tyrosol is incorrect? A 1 mol of Tyrosol will react with 2 mol of Na to give 1 mol of H2. B 1 mol of Tyrosol will react with 2 mol of PCl5 to give 2 mol of HCl. C Tyrosol will react with acidified KMnO4 under reflux to give a carboxylic acid. D Tyrosol will react with H2SO4 under suitable conditions to give an alkene. CJC Prelim 2010

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25 Catechin is an antioxidant found in tea leaves, chocolates and red wine. It is often studied for its function as an inhibitor to the growth of cancer cells among other health benefits.
OH HO O

OH OH

OH

Catechin

ring is not involved in any of the following reactions. Which statement about catechin is correct? A It can undergo oxidation with hot acidified K2Cr2O7. B It can undergo electrophilic addition with Br2(aq). C 1 mol of catechin can react with 5 mol of NaOH. D 1 mol of catechin can react with 4 mol of Na2CO3.

CJC Prelim 2010

26 Which of the following about the amino acid, methionine, is true?

A B C D

It acts as a buffer in a solution of pH 13. It exists predominantly as a zwitterion in a solution of pH 2. It exists as a crystalline solid with high melting point. It forms covalent disulfide linkage with another methionine molecule. CJC Prelim 2010

27 Which sequence shows the compounds in order of decreasing pKa values? A CH3CO2H > CF3CO2H > C2H5OH > C6H5OH B CF3CO2H > CH3CO2H > C6H5OH > C2H5OH C C2H5OH > C6H5OH > CH3CO2H > CF3CO2H D C6H5OH > C2H5OH > CH3CO2H > CF3CO2H HCI Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

28 Compound X undergoes oxidative cleavage with hot acidified KMnO4 to give a single organic product. The organic product formed gives a yellow precipitate when heated with aqueous alkaline iodine, but does not react with sodium carbonate. Which could be the identity of Compound X?

CJC Prelim 2010 29 The carbon-nitrogen bond length in methylamine is longer than that in formamide.

What helps to explain the shorter carbon-nitrogen bond length in formamide? 2 2 A It is a sp -sp overlap. B Formamide is a weaker base than methylamine. C The electrons in the filled p orbitals on C and N of methylamine repel each other. D The electron withdrawing C=O group in formamide draws the lone pair of electrons CJC Prelim 2010 30 An alkane E with the molecular formula C4H10 reacts with chlorine gas in the presence of light to form two monochlorinated alkanes F and G in the molar ratio of 9:1. What are the structures of E and F? E F A CH3CH2CH2CH3 CH3CH2CH2CH2Cl B CH3CH2CH2CH3 CH3CH2CHClCH3 C CH3CH(CH3)CH3 CH3CCl(CH3)CH3 D CH3CH(CH3)CH3 CH3CH2CH2CH2Cl HCI Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

31 Hydrocortisone is a steroid hormone produced by the adrenal gland and is released in response to stress. It is commonly used as an active ingredient in anti-inflammatory creams.

Which of the following statements about hydrocortisone is true? A Treated with NaBH4 in the presence of methanol, it forms a compound containing 5 hydroxy groups. B When warmed with aqueous alkaline iodine, a yellow precipitate is observed. C When treated with cold dilute KMnO4, it forms a compound containing 2 hydroxy groups. D When treated with an excess of hot concentrated acidified KMnO4, it forms a compound containing 7 chiral centres. CJC Prelim 2010 32 Loviride was once used as an antiviral drug in clinical trials and is structurally similar to Compound Z.

Which reagent could be used to distinguish Loviride from Compound Z? A aqueous alkaline iodine B aqueous bromine C aqueous sodium hydroxide D hot acidified potassium manganate(VII) CJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

33 A pheromone is a secreted or excreted chemical factor that triggers a social response in members of the same species. Compound A below is an example of pheromones.
CH3 OH

CH3

HO

Compound A

How many possible isomers, including stereoisomers, can be obtained when A is heated with excess concentrated sulfuric acid? 6 7 A 2 B 2 C 28 D 29 HCI Prelim 2010 34 Benzene undergoes Friedel-Crafts acylation with ethanoyl chloride to form phenyl ethanoate, which can be represented as follow:
O C CH3COCl AlCl3 CH3

The mechanism of the above reaction is similar to that of the bromination of benzene. Which of the following statements is not correct about the mechanism? A The organic intermediate has a ring with one sp3 hybridised carbon. B The mechanism involves CH3CO+ as an electrophile. C The overall order of reaction is 1. D AlCl3 is a homogeneous catalyst. HCI Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

35 Saccharin was an artificial sweetener used in some soft drinks. It was manufactured from methylbenzene by a series of reactions.
CH3 ClSO3H I CH3 SO2Cl NH3 II CH3 SO2NH2 O C N SO2 H

Which of the following shows the correct reaction type for steps I and II? I II A electrophilic substitution electrophilic addition B electrophilic substitution nucleophilic substitution C nucleophilic substitution electrophilic substitution D nucleophilic substitution nucleophilic addition HCI Prelim 2010 36 The following compound is tested with two reagents separately.
OH O C H

What are the expected observations? Warm with Fehlings reagent Warm with Tollens reagent A Brick-red precipitate Silver mirror B No precipitate Silver mirror C Brick-red precipitate No silver mirror D No precipitate No silver mirror
O CH3

HCI Prelim 2010

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37 1 mole of an organic compound X reacts with 1 mole of NaOH. 1 mole of X also reacts with PCl5 to produce 1 mole of hydrogen chloride. Which compound could be X? A B C D

HCI Prelim 2010 38 Paracetamol is a common analgesic used in the treatment of fever and headaches.
H N C O HO CH3

Which deduction about paracetamol can be made from this structure? A It is a planar molecule. B It contains an amine group. C It reacts with sodium metal. D It gives an orange precipitate with 2,4-dinitrophenylhydrazine. HCI Prelim 2010 39 The same product is obtained when separate samples of P and Q are respectively heated in a sealed tube with ammonia and reacted with lithium aluminium hydride in dry ether. Which are the structures of P and Q? P Q A C6H5Br C6H5CN B CH3CH(Br)CH3 CH3CH(CN)CH3 C CH3CH2CH2Br CH3CH2CN D CH3CH(Br)CH3 CH3CH2CN HCI Prelim 2010
paracetamol

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40 The reaction scheme below shows the synthesis of compound S.

Cl CH3 Br NaOH(aq) heat K2Cr2O7/H2SO4(aq) heat

Which of the following can be S?

OH
Cl CH3 O

O O CH3 C C OH C OH

A
OH CH3 O

C
O C HO Cl

O
O C

OH OH C

HCI Prelim 2010

41 Estragole is an organic compound found in the essential oils of various plants. It can be synthesised from chavicol, a compound used in perfumes.
OH OCH3

estragole Which of the following reagents and conditions can be used to carry out the above conversion? A NaOH, followed by CH3OH C NaOH, followed by CH3Br B Na2CO3, followed by CH3I D Na2CO3, followed by CH3OH IJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg) chavicol

42 Carbonyl compounds undergo condensation reactions with 2,4 dinitrophenylhydrazine as shown in the equation below.

Which pair of compounds could be used to form the compound shown below?
H3C C N N C CH3

A B C D C6H5(CH3)C=NH and C6H5(CH3)C=NH C6H5CHO and C6H5(CH3)C=NNH2 C6H5COCH3 and H2NNH2 C6H5COCH3 and C6H5(CH3)C=NH

IJC Prelim 2010 43 The antibiotic chlortetracycline is commonly used to treat conjunctivitis in cats. It has the formula shown.
OH O O OH OH OH H2N

O H N H HO Cl

How many stereoisomers are possible for chlortetracycline? A 24 C 26 B 25 D 27

IJC Prelim 2010

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44 What is the number of sp and sp carbon atoms in the structure given below?
H H H C C H C O CH3

A B C D

sp2 7 1 4 3 sp3 3 3 6 7 IJC Prelim 2010

45 A new industrial preparation of ethyl ethanoate has been developed using cheap sources of ethanol.
Cu catalyst CH3CH2OH - H2 CH3CHO Cu catalyst + CH3CH2OH CH3CH(OH)OCH2CH3 Cu catalyst - H2 CH3CO2CH2CH3

IJC Prelim 2010 46 A certain organic compound reacts vigorously with water to give an acidic solution which instantly yields a precipitate of silver bromide when treated with aqueous silver nitrate. What could be the compound? A BrCH2CH2COOH C CH3CH2COBr B C6H5Br D CH3CH(OH)CH2Br IJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

Which process is involved at some stage in this reaction sequence? A disproportionation C nucleophilic addition B electrophilic addition D reduction

47 Concentrated sulfuric acid is often used in organic reactions as a strong acid, dehydrating agent, catalyst or oxidising agent. In which of the following reactions is concentrated sulfuric acid not acting in one of the above functions? A
CH3CH2OH conc. H2SO4

B CH3CH2OH + CH3COOH
C2H4 + H2SO4

C2H4 + H2O conc. H2SO4

H H C H

CH3CO2CH2CH3 + H2O H
C H

C D

OSO3H

48 Chlorofluroalkanes, commonly known as CFCs, undergo homolytic fission in the presence of ultraviolet radiation in the stratosphere. Which radical is likely to be produced from the radiation on CHFClCF2Cl? A CHFCF2Cl B
CHFClCFCl

IJC Prelim 2010

C CHClCF2Cl D CFClCF2Cl IJC Prelim 2010

49 In the tertiary structure of a water-soluble globular protein extracted from barley grains, it was found that the types of amino acid residues present on the outer surface of the protein were different from those present on the inside. Which of the following amino acids is most likely to be incorporated into the outer surface of such proteins?
H H C
H H C

COOH

COOH

A
H

H N

CH(CH3)2 H
C COOH

C
H H N

CH2SH

H C H

COOH

CH2COOH

IJC Prelim 2010

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50 When ethene reacts with HBr in the presence of aqueous NaNO3, what are the two possible products formed?
H C Br H
H C H H

H C

and

C Br H

C OH H
C

Br H
C Br H H and H

C Br H

B
H

ONO2 H

C H H

C Br H
C OH

and

C H H

C OH H
C

C
H

C Br

and

C H

ONO2

IJC Prelim 2010

51 The psychoactive drug in cannabis has the following structure.

H3C HO

C H3C

CH2

OH

Which statement about the above molecule is incorrect? A Effervescence is observed when heated with purple potassium permanganate (VII). B It has 8 stereoisomers. C It produces 5 moles of HBr when reacted with aqueous bromine under room temperature. D The solubility of the compound increases in aqueous NaOH. IJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

52 Glutamic acid has a pKa value of 4.3 and residues of this amino acid are present in the -chains of haemoglobin.

Which of the following structures shows glutamic acid residue in its most stable state when a sample of haemoglobin is hydrolysed and the solution is subsequently adjusted to pH=7?

IJC Prelim 2010

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 53 2,2-dimethylbutane was reacted with limited chlorine in the presence of UV light. Assuming that only mono-chlorination takes place, what is the ratio of the products obtained? 1-chloro-2,2- 3-chloro-2,2- 1-chloro-3,3- dimethylbutane dimethylbutane dimethylbutane A 3 3 3 B 3 2 3 C 9 2 3 D 9 2 2 MJC Prelim 2010 54 A nitrile Q is treated with LiAlH4 to give a compound of the formula C2H7N. In a separate reaction, Q was hydrolysed in acidic medium. What would be formed if the products from these two reactions were mixed together? A CH3CONHCH2CH3 B CH3CH2CONHCH2CH3 C (CH3CO2 )(CH3CH2NH3+) D (CH3CH2CO2 )(CH3CH2NH3+) MJC Prelim 2010 55 Which method is able to separate benzene from a mixture of benzene, methylbenzene and phenol? A shaking the mixture with aqueous Br2 B shaking the mixture with hot ethanoic acid and concentrated H2SO4 C shaking the mixture with hot concentrated HNO3 and concentrated H2SO4 D shaking the mixture with hot acidified KMnO4, followed by excess dilute NaOH MJC Prelim 2010

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56 Which of the following shows a correct mechanistic step in the reaction between the stated reagents? Reagents Step chloropropane and A ethanolic sodium hydroxide, heat

propanal and hydrogen cyanide, trace amount of sodium hydroxide, cold benzene and chlorine in presence of iron catalyst propene and bromine monochloride in tetrachloromethane

MJC Prelim 2010

57 A new industrial preparation of propyl propanoate has been developed using cheap sources of propanol.

Which process is involved at some stage in this reaction sequence? A Disproportionation B Electrophilic Addition C Nucleophilic Addition D Reduction MJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

58 . Which statement about Pravastatin is likely to be correct?

Pravastatin

A It reacts with only 3 moles of phosphorus pentachloride at room temperature and pressure. B It reacts with only 3 moles of hydrogen gas in the presence of nickel catalyst and heat. C It reacts with acidified potassium manganate(VII) under reflux to form one organic product. D It reacts with liquid bromine in tetrachloromethane to form a compound with 12 chiral centres. MJC Prelim 2010 59 Which of the following is arranged in decreasing order of solubility in water? A sodium propanoate, propanoic acid, propanol, propanal B sodium propanoate, propanoic acid, propanal, propanol C propanoic acid, propanol, propanal, sodium propanoate D propanal, propanol, propanoic acid, sodium propanoate MJC Prelim 2010 60 What is the correct order of increasing pKa for the following compounds?

A E, F, H, G B G, E, F, H C G, F, E, H D H, F, E, G Compiled by Twig Learning Center (http://www.twig.com.sg)

MJC Prelim 2010

2 61 Deuterium, D, is an isotope of hydrogen, 1 H . Which reaction will not yield a stable organic compound containing deuterium?

C D

M JC P relim 2010

62 Which reagent will give a visible observation when it is added to compound K?

Compound K A B C D hot alkaline iodine hot hydrochloric acid aqueous sodium hydrogencarbonate hot acidified potassium dichromate(VI)

MJC Prelim 2010

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63 A polypeptide was digested using two different enzymes. The fragments obtained were separated using electrophoresis. Analysis of the fragments from each digestion gave the following results: Digestion using enzyme N: Digestion using the enzyme O: thr-phe-leu val-asp-cys-thr cys-glu-val phe-leu-ser ser-glu-cys glu-cys asp-cys cys-glu What is the correct sequence of the polypeptide structure? A cys-glu-val-ser-glu-cys-asp-cys-thr-phe-leu B cys-glu-val-asp-cys-thr-phe-leu-ser-glu-cys C glu-cys-glu-val-asp-cys-thr-phe-leu-ser-glu D ser-glu-cys-glu-val-asp-cys-thr-phe-leu-ser MJC Prelim 2010 64 Which of the following statements about the molecule shown below is correct?

A B C D

It can exist as geometric isomers. It reacts with 3 moles of hydrogen bromide. It undergoes nucleophilic addition reactions. It reacts with acidified potassium dichromate(VI).

NJC Prelim 2010

65 The structure of cortisone is shown below.

When it is completely reacted with lithium aluminum hydride with ether at room temperature, how many chiral centres does the product molecule possess? A 7 B 8 C 9 D 10 NJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

66 The following are the likely products when 2-bromo-2-methylbutane reacts with ethanolic potassium hydroxide except A 2-methylbut-1-ene B 1-methylbutan-2-ol C 2-methylbutan-2-ol D 2-methylbut-2-ene NJC Prelim 2010 67 The Williamsons ether synthesis involves a nucleophilic substitution of an organic halogen compound. Which of the following reagents can be used for the synthesis of methoxyethane, CH3CH2OCH3 starting from bromoethane? A sodium hydroxide in methanol B sodium with methanol C potassium ethoxide D methanol NJC Prelim 2010 68 The reaction of ethanol with sulfuric acid is shown in the scheme below:

Which of the following is not true of the above scheme? A Concentrated phosphoric acid can be used in place of concentrated sulfuric acid in reaction I. B This reaction always yields a mixture of the two products. C Reactions I and III involve the same mechanism. D Reaction II shows the elimination of water. NJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

69 Which of the following cannot be used to distinguish between the following compounds?
O O HO CHO

A B C D

Hot acidified K2Cr2O7 Neutral iron(III) chloride Silver diammine complex 2,4-dinitrophenylhydrazine

NJC Prelim 2010

70 A student treated benzene in a 3-step reaction to yield Nphenyethanamide, Which of the following gives the correct sequence? Step 1 Step 2 Step 3 A Ethanolic potassium cyanide Sn, conc HCl Propanone B Conc H2SO4 and conc HNO3 LiAlH4 in dry ether Ethanoyl chloride C Conc H2SO4 and conc HNO3 Zn, conc HCl Ethanoyl chloride D Chlorine in presence of FeCl3 Ethanolic ammonia Ethanoyl chloride NJC Prelim 2010 71 Which of the following shows the correct order of increasing base strength?
NHCOCH3

NJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

72 Which of the following is the least likely reaction of compound X?

NJC Prelim 2010 73 Anhydrides are acid derivatives which can be considered to be formed from the dehydration of acids. The chemistry of the acid anhydrides is very similar to that of the acid chlorides, except that they are a little less reactive. The formation of benzoic anhydride is shown below:
COOH COOH CO O CO

Which of the following is not true for benzoic anhydride? A It reacts with ethanol. B It has little solubility in water. C It reacts with aqueous sodium hydroxide to give the sodium salt. D It gives an orange solid when reacted with 2,4-dinitrophenylhydrazine. NJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

74 A carbonyl compound can be converted into an alkene by means of the Wittig reaction where a phosphorus ylide is involved as follows:

Which of the following pairs of compounds might you use to prepare the following alkene?
CH3

NJC Prelim 2010 75 As the number of carbon atoms in the homologous series of alkane molecules increases, which property of the alkanes does the numerical value decrease? A density B enthalpy change of vaporisation C number of isomers D vapour pressure NYJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

76 A compound has the following structural formula:

SO3H

What is the shape of the molecule with respect to the S atom and how many p electrons are present in one molecule of the compound? shape A trigonal bipyramidal 10 B tetrahedral 10 C trigonal bipyramidal 12 D tetrahedral 12 NYJC Prelim 2010 77 The drug cortisone has the formula shown below.
CH2OH CO O OH

CO2CH3

How many chiral centres are present when cortisone is treated with cold acidified KMnO4(aq)? A 5 B 6 C 7 D 8 NYJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

78 Oxidation of an alkene X gives a diol; further oxidation gives a diketone. Which one of the following could be X? A (CH3)2C=C(CH3)2 B CH3CH=C(CH3)2 C C6H5CH=CHC6H5 D (C6H5)2C=CH2

NYJC Prelim 2010

79 Compound B is formed from compound A in the presence of AlCl3.

O O CH3 CH2Cl + AlCl3

Compound A

What is the mechanism of the above reaction? A electrophilic addition B electrophilic substitution C nucleophilic substitution D nucleophilic addition

Compound B

NYJC Prelim 2010

80 Which reagent gives a colourless homogeneous solution when added to phenol? A aqueous bromine B aqueous sodium carbonate C aqueous sodium hydroxide D neutral aqueous iron(III) chloride NYJC Prelim 2010

81 The following molecule CH3CH2CH(COCl)CH(CH3)OCOH is subjected to heating with alkali. What are the products of this reaction? - A CH3CH2CH(CO2 )CH(CH3)OH + CO32- - B CH3CH2CH(CO2H)CH(CH3)O + HCO2- - C CH3CH2CH(CO2 ) CH(CH3)OH + HCO2- D CH3CH2CH(CO2H)CH(CH3)OH + CO32- NYJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

82 In which sequence is it correctly stated that the value of pKa decreases continuously?
COOH COOH OH OH

> A
H2N COOH

>
COOH

>
O2N OH OH

> B
H2N OH

>
O2N OH

>
COOH COOH

> C
NC OH

>
CH3O COOH

>
OH COOH

> D
CH3O

>
NC

>

NYJC Prelim 2010 83 Which of the following compounds is least soluble in water? A CH3CH(NH2)COOH B C6H5CH(OH)CH3 C C6H5CH2N(CH3)2 D C6H5CO2Na

NYJC Prelim 2010

84 In a beehive, the queen bee secretes the substance below to cause worker bees to begin constructing royal colony cells. CH3CO(CH2)5CH=CHCO2H queen bee substance From the structure shown, which one of the following statements about the queen bee substance is correct? A It gives a positive test with an aqueous solution containing Ag(NH3)2+ B It gives an orange precipitate with alkaline aqueous iodine. C It gives fumes of HCl gas with PCl5. D Reaction with hydrogen over a catalyst produces CH3CH(OH)(CH2)8OH. NYJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

85 Maytansine is a potent antitumour agent. How many chiral centres are present in the product of the reaction between Maytansine and Br2 in CCl4 in the dark?
O Cl CH3O N O O O N O

O N OH OCH3 O

Maytansine A 8 B 10 C 12 D 14

RJC Prelim 2010

86 How many H atoms are in the same plane as Ha in the following molecule?
Ha C C C H H H

A 0 B 1

C 2 D 3

RJC Prelim 2010

87 Arrange the following compounds in order of decreasing Kb.

N H I O CH3 C N II CH3CH2 III NH2 IV NH2

A I, IV, III, II B I, III, IV, II

C II, IV, III, I D II, III, IV, I

RJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

88 In which of the following pairs does reaction I take place more rapidly than reaction II?
CH3CH2CH2Br + CH3S

I II

CH3CH2CH2SCH3 + Br

A CH3CH2CH2Br + CH3SH
(CH3)3CCl + H2O I II
3

CH3CH2CH2SCH3 + HBr

(CH3)3COH + HCl (CH3)3COH + HBr

I (CH3)3COCH2CH3 + Cl

B (CH3)3CBr + H2O

(CH3)3CCl (1 mol dm ) + CH3CH 2O (2 mol dm3) (CH3)3CCl (1 mol dm3) + 3 C CH3CH 2O (1 mol dm )

II (CH3)3COCH2CH3 + Cl

C6H5OH + HCl (CH3)3COH + HCl

C6H5Cl + H2O

I II

D (CH3)3CCl + H2O

RJC Prelim 2010

89 A chloroalkane W with molecular formula of C5H11Cl exhibits optical activity. On warming W with alcoholic NaOH, two alkenes X and Y are formed, X being the major product. One of the products of the reaction between X and hot acidified potassium manganate(VII) gives a yellow precipitate with alkaline aqueous iodine. Which of the following could be W? A CH3CHClCH2CH2CH3 C CH3CH(CH3)CHClCH3 B CH3CH2CHClCH2CH3 D CH3CCl(CH3)CH2CH3 RJC Prelim 2010 90 An organic compound has the following properties: (i) It gives a yellow precipitate with alkaline aqueous iodine solution. (ii) It gives an orange precipitate with 2,4-dinitrophenylhydrazine. (iii) It forms a brick-red precipitate with Fehlings solution. Which compound could give these results? A CH3COCH2C(OH)(CH3)CH2CHO B CH3COCH=CHCH(CH3)CO2H C CH3COCH2COCH2CH3 D CH3COCH2C6H4CHO RJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

91 Which of the following can be used to distinguish between the following two compounds?
OH O O

OH

O O

A B C D hot acidified K2Cr2O7 hot acidified KMnO4 neutral FeCl3(aq) Br2(aq)

CH2=CH

RJC Prelim 2010

92 Consider the reaction between butanone and hydrogen cyanide in which the enthalpy change of the reaction is near zero. Which one of the following statements is incorrect? A The reaction is catalysed by a small amount of base. B The slow step involves the formation of a CC bond. C The Gibbs free energy of the reaction is positive at high temperatures. D The reaction between butanal and hydrogen cyanide is slower than the reaction between butanone and hydrogen cyanide. RJC Prelim 2010 93 How many stereoisomers are possible for the following compound?

A 0 B 2

C 4 D 8

SAJC Prelim 2010

Compiled by Twig Learning Center (http://www.twig.com.sg)

94 What is the structure of Q in the following reaction scheme?

CH3 CH3 CH3 C KMnO4 / aq H2SO4 heat

SOCl2 P Q

HOCH2CH2

COCH3
CH3 CH3 CH3 C

O C Cl

Cl

C O
O Cl

C O

Cl

Cl

C O

C O

Cl

CH3 O

CH3 CH3 C

Cl

C O

C O

CH3

Cl

CH2

C O

Cl

RJC Prelim 2010

95 The Russian composer Borodin was also a research chemist who discovered a reaction in which two ethanal molecules combine to form a compound commonly known as aldol (reaction I). Aldol forms another compound on heating (reaction II). I 2CH3CHO CH3CH(OH)CH2CHO II CH3CH(OH)CH2CHO CH3CH=CHCHO + H2O Which one of the following would be produced when acetone, CH3COCH3 undergoes the same reactions? A CH3CH=CHCOCH3 C CH3COCH=C(CH3)2 B C(CH3)2=CHCHO D CH3CH=CHCH3 SAJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

96 A key molecule in the chemistry of vision is the highly conjugated rhodopsin, which is synthesised in the rod cells of the eye from 11-cis-retinal and a primary amine in the protein opsin.
NH2 opsin

H 11-cis-retinal

O rhodopsin

opsin

Which of the following statements is correct? A 1 mole of 11-cis-retinal reacts with 5 moles of hydrogen gas. B The reaction between 11-cis-retinal and NH2-opsin is a condensation reaction. C The reaction of 11-cis-retinal with LiAlH4 produces a product that is optically active. D The reaction between 11-cis-retinal with hot acidified potassium manganate(VII) produces a total of five different organic products. RJC Prelim 2010 97 Which sequence shows the compounds in increasing order of pKa values?
OH CH3CH2 I CH3NH II OH F III IV OH OH

SAJC Prelim 2010 98 Which of the following compounds, on complete oxidation with hot acidified potassium manganate(VII), would give two organic compounds? A (CH3)2C=CHCH2CH2CH=CH2 C CH3(CH2)2CH=CH(CH2)2CH3 B CH3(CH2)4CH=CHCH2OH D C6H5CH2CH3 SAJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

A I, II, III, IV B IV, II, III, I

C II, I, III, IV D III, IV, I, II

99 Aspartame, a non-nutritive sweetener marketed under the trade name NutraSweet, is the methyl ester of a simple dipeptide, AspPheOCH3. The structures of Asp and Phe are shown as follows:
H H2N C COOH
H H2N C COOH CH2COOH

CH2

Asp

Phe

The isoelectric point of aspartame is 5.9. Which of the following is the predominant species present in an aqueous solution at physiological pH 7.3?
H O CH2 COO

H CH2

H3N C C NH C COOCH3

H O CH2 COOCH3

H CH2

H2N C C NH C COO

H O CH2 COOCH3

H CH2

H3N C C NH C COO

H O CH2 COO

H CH2

H2N C C NH C COOCH3

RJC Prelim 2010

Compiled by Twig Learning Center (http://www.twig.com.sg)

 100

The structures of some amino acids are shown below: glutamic acid
H H2N C COOH (CH2)2 COOH

lysine

H H2N C COOH (CH2)4 NH2

phenylalanine

H H2N C COOH CH2

serine

H H2N C COOH CH2OH H

H2N C COOH CH3 CH CH3

valine

Which of the following pairs of amino acids are likely to be found on the outside of a globular protein, and which on the inside? on the outside on the inside A glutamic acid and lysine valine and phenylalanine B valine and phenylalanine glutamic acid and lysine C serine and lysine valine and glutamic acid D glutamic acid and valine phenylalanine and serine RJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

101 A hexapeptide gave the following peptide residues upon partial hydrolysis: Val-His, Leu-Ala, Val-Phe, His-Val and Phe-Leu. What is the structure of the hexapeptide? A Val-His-Val-Phe-Leu-Ala C Phe-Leu-Ala -His-Val-Phe B Ala-Leu-Phe-Val-His-Val D His-Val-Phe-Leu-Ala-Val SAJC Prelim 2010 102 A compound U has all the following properties. - It reacts with aqueous Na2CO3 - It gives a brick red precipitate with Fehlings solution. - It gives a green colouration with hot acidified K2Cr2O7. What could U be?

SAJC Prelim 2010

103 Which of the following organic compounds would give a yellow precipitate on heating with aqueous alkaline iodine?

SAJC Prelim 2010

Compiled by Twig Learning Center (http://www.twig.com.sg)

104

The structure of Q is as shown:

What would be formed by prolonged boiling of Q with aqueous sodium hydroxide?

SAJC Prelim 2010

105 The two-stage reaction sequence given below shows a possible mechanism for the reaction between hydroxide ion and an organic compound:

The overall reaction should be classified as A Electrophilic addition C Nucleophilic addition B Electrophilic substitution D Nucleophilic substitution SAJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

106 A B C D 107

Which of the following synthetic routes does not produce ethanoic acid?
CH3CH(OH)CH3 aqueous alkaline iodine heat H+ r.t.p. acidic K2Cr2O7 heat

excess conc H2SO4 CH3CH(OH)CH2CH3 180oC alcoholic KCN dil HCl CH3Br reflux heat
CH3CHO [Ag(NH3)2]+ heat H+ r.t.p.

TJC Prelim 2010

What reagent can be used to distinguish between the following isomers?

CO2H NH2

CONH2 OH

A B C D

108 Compound X shows the following chemical properties. I) It does not give any observation with Fehlings solution. II) 1 mole of compound X reacts with 2 moles of sodium metal. III) When PCl5(s) is added to compound X, a sweet smelling product is obtained. Which of the following structures can compound X be? A HO2CCH2CH2CH2CO2H B HO2CCH2CH2CH2CHO
O H C OH
O H C OH CH2CO2H

Aqueous NaOH, heat Na metal, room temperature and pressure Aqueous bromine, room temperature and pressure LiAlH4, dry ether, room temperature and pressure

TJC Prelim 2010

CH2CH2OH

TJC Prelim 2010

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109

The uncatalysed addition of HCN to a carbonyl group to give a cyanohydrin proceeds by two steps.
O H3CH2C C + H H3CH2C CN C H CN O:- + H CN H3CH2C C H OH + :CN O-

Step I

- :CN +

CN Step II H3CH2C C H

110

The rate equation for the formation of cyanohydrin is as follows. Rate = k[CH3CH2CHO][CN-] Which of the following statements is correct? A Step II is rate determining. B The reaction will proceed slower if small amount of NaOH is added. C A same product can be obtained by refluxing 1-chloropropan-1-ol with HCN. D The uncatalysed addition of HCN to propanone occurs at slower rate than that for propanal. TJC Prelim 2010 Which of the following shows the correct order of increasing acidity?

TJC Prelim 2010

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111 A B C D 112

1,2-dibromo-3-chloropropane (DBCP) has been used in the control of earthworms in agricultural land. Which of the following would be the best synthesis of this compound? CH3CH2CH2Cl + 2Br2 DBCP + 2HBr CH2BrCHBrCH3 + Cl2 DBCP + HCl ClCH2CH=CH2 + PBr5 DBCP + PBr3 CH2=CHCH2Cl + Br2 DBCP

TJC Prelim 2010

-Cadinene is present in the oil derived from the plant juniper woods. X is the major compound when -Cadinene is reacted with HBr in CCl4. How many chiral carbons does X have?
CH3 HBr/ CCl4 H3C H3C CH3

Major product X

A 3 B 4 113

C 5 D 6

TJC Prelim 2010

The structure of the alkaloid ephedrine is shown below.

OH CH3 C H C H N CH3 H

Which of the following will be properties of the alkaloid? A It reacts with excess concentrated H2SO4 at 180C to give a chiral product. B It gives a violet complex with neutral FeCl3. C When warmed with acidic KMnO4, its product gives a silver mirror with Tollens reagent. D 0.2 mol of ephedrine reacts with 0.1 mol of HCl(aq) to give a buffer solution. TJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

114 Four drops of 1-chorobutane, 1-bromobutane and 1-iodobutane were put separately into three test-tubes containing 1.0 cm3 of aqueous silver nitrate at 60C. A hydrolysis reaction occurred. (R represents the butane chain C4H9 and X the halogen atom.) H2O(l) + RX(l) + Ag+(aq) ROH(aq) + AgX(s) + H+(aq) The rate of formation of cloudiness in the tubes was in the order RCl < RBr < RI. Why is this? A The R-X bond polarity decreases from RCl to RI. B The solubility of AgX(s) decreases from AgCl to AgI. C The ionisation energy of the halogen decreases from Cl to I. D The bond energy of R-X decreases from RCl to RI. TJC Prelim 2010 115 Ethanol reacts explosively with sodium metal to form a salt, sodium ethoxide. What is the product of the reaction between 2-iodobutane and sodium ethoxide? A CH3CH=CHCH3 B (CH3)2CHCH2OCH2CH3 C CH3CH2CH(OCH3)CH2CH3 D CH3CH2CH(CH3)OCH2CH3 TJC Prelim 2010 116 -Caryophyllene is an odiferous sesquiterpene used by the cotton plant to attract the male cotton boll weevil.
CH3

CH3

CH 2

X is the major product formed when -caryophyllene is reacted with HBr in CCl4. How many stereoisomers does X have? A 4 C 16 B 8 D 32 VJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

CH 3 - Cary ophyl lene

117

An alkyne (CC) undergoes hydration in a similar mechanism as an alkene. However, the formation of enol (C=C-OH) is unstable and would undergo rearrangement to form a carbonyl compound.
hydration R C C H R OH C H C H O rearrangement R C C H H H

Which compound will not be formed when the following alkynes undergo hydration?

C D

118

VJC Prelim 2010 Which statement best describes the reaction mechanism involved in the single step conversion of chloroethane to ethanol?

A The reaction involves removal of HCl, followed by the addition of H2O. B The reaction involves heterolytic fission of the CCl bond, followed by a reaction with H2O. C The reaction involves nucleophilic attack of OH in a bimolecular mechanism. D The reaction mechanism involves a carbocation. VJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

119

Which type of reaction does the following compound not undergo?

A electrophilic addition B electrophilic substitution

HOCH2CH2COCH2

CO2H

C nucleophilic addition D nucleophilic substitution VJC Prelim 2010

120 Which of the following compounds react with hot acidified KMnO4 and the resultant product formed will give a positive test with both 2,4-dinitrophenylhydrazine and PCl5?

B 121

VJC Prelim 2010 Consider the compound Y which has the structural formula as shown.
CH2 Cl

Cl

CH=CHCH2 Cl

compound Y

1 mole of compound Y is warmed with excess aqueous sodium hydroxide. The resulting solution is cooled and acidified with dilute nitric acid. How many moles of silver chloride will be precipitated out when excess aqueous silver nitrate is then added? A 0 B 1 C 2 D 3 VJC Prelim 2010

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122

Which of the following 2-stage processes will not yield the final product as shown?

VJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

123

A mixture is made by mixing excess aqueous sodium carbonate with phenylmethanol, phenol and methanoic acid. Which organic species is/are present in the organic layer of the solution? C phenylmethanol and phenol D phenylmethanol, phenol and methanoic acid VJC Prelim 2010 Enalapril is used to treat hypertension.
CH2CH2CHCO2CH2CH3 NHCH(CH3)CONH Enalapril CO2H

A phenylmethanol B methanoic acid 124

Which of the following statements about Enalapril is true? A Enalapril decolourises acidified K2Cr2O7. B Enalapril gives an orange precipitate with 2,4-dinitrophenylhydrazine. C One mole of Enalapril reacts with 3 moles of CH3COCl. D One mole of Enalapril reacts with 3 moles of NaOH. VJC Prelim 2010 125 Compound M can be synthesised as shown below.
O HO OH Compound M

HOCH2CH2CH=CH2

II

III

What are the reagents used for steps I, II and III? I II + A H /KMnO4(aq) PCl5 + B H /KMnO4(aq) PCl5 C 1. concentrated H2SO4 NaOH(aq), I2(aq) 2. H2O D 1. concentrated H2SO4 OH /KMnO4(aq) 2. H2O Compiled by Twig Learning Center (http://www.twig.com.sg)

III NaOH(aq) H2O HCl(aq) HCl(aq) VJC Prelim 2010

126

When equimolar amounts of organic compounds R, S, T and U are added separately to water, solutions of increasing pH values are obtained. Which set of identities of compounds R to U is correct?

T U A CH3CH2CO2H CH3CHClCH2NH2 B CH3CHClCH2NH2 CH3CH2CO2H C CH3CH2CO2H CH3CHClCH2NH2 D CH3CHClCH2NH2 CH3CH2CO2H VJC Prelim 2010 127 Which compound decolourise brown bromine in the dark?
OH

R S CH3CH2CO2H CH3CH2COCl CH3CH2CO2H CH3CH2COCl CH3CH2COCl CH3CH2CO2H CH3CH2COCl CH3CH2CO2H

CH3
NO2

A
CN

C
CO2H

CH2NH2

B 128

Cl

NH2

VJC Prelim 2010

Ibuprofen is a powerful painkiller.

H CH3 C OH Ibuprofen COOH CH2 CH3 C OH CH3

Which of the following statements about Ibuprofen is correct? A 1 mol of Ibuprofen can evolve 3 mol of H2. B 1 mol of Ibuprofen reacts with 2 mol of HCl. C The bond angle around all carbon atoms is 109.5o. D It will decolourise aqueous bromine to give a white precipitate. Compiled by Twig Learning Center (http://www.twig.com.sg)

PJC Prelim 2010

129 A B C D

Which of the following represents the correct sequence of increasing pKa value of the four acids? CCl3CO2H CCl3CO2H C6H5OH C6H5OH < CH3CO2H < < CH3CO2H < < C2H5OH < < C2H5OH < C6H5OH C2H5OH CCl3CO2H CH3CO2H < < < < C2H5OH C6H5OH CH3CO2H CCl3CO2H

130

PJC Prelim 2010 Which of the following pairs of protein segments has an interaction which is likely to be broken due to a change in pH?
NH
NH

O CH2

CH CO

and

NH3

(CH2)4

CH CO

NH

NH

B HS CH2 CH
CO
CH2

and HS CH2 CH
CO

CH2 CH2

NH CH and CO

O O C

NH CH CO

NH

NH

D HO CH2

CH CO

and HS CH2

CH CO

VJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

The responses A to D should be selected on the basis of A B C D 1, 2 and 3 1 and 2 only 2 and 3 only 1 only is are correct are correct are correct correct 131 Which of the following is a suitable chemical test to distinguish the below two compounds?
H3C H3C OH

OCH 3

OCH 3

H3C

HO

CH3

H3C

CH3

ACJC Prelim 2010 132 Which compounds liberate ammonia when boiled with aqueous sodium hydroxide? 1. CH3CH2CN 2. CH3CH2CONH2 3. CH3CH2CO2NH4 ACJC Prelim 2010 133 Which of the following statements are true for compound A?

1. Cold dilute KMnO4 2. Hot acidified K2Cr2O7 3. Warm alkaline I2

1. It gives a orange precipitate with 2,4-dinitrophenylhydrazine. 2. It gives a silver precipitate with Tollens reagent. 3. It undergoes esterification with phenol. ACJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

134 Which of the following tests can be used to distinguish between the compounds W and X?

1. Na metal 2. hot aqueous AgNO3 3. hot acidified K2Cr2O7

ACJC Prelim 2010

135 A compound has a relative molecular mass of 88 and its molecule contains only four carbon atoms. What could this compound be? 1. a primary alcohol containing a ketone group 2. a secondary alcohol containing an aldehyde group 3. a saturated noncyclic diol AJC Prelim 2010 136 Which statements are true for an SN2 reaction? 1. One bond is broken before another bond is formed. 2. The formation of a transition state involves the collision of two molecules or ions. 3. A carbon atom in the transition state is bonded, either fully or partially, to five other atoms. AJC Prelim 2010 137 A manufacturer needs a stronger base than methylamine, CH3NH2, to add to a cleansing fluid. Which of the following would not be appropriate? 1. (CH3)2NH 2. CH3NH3+Cl 3. CH3CONH2 AJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

138

Consider the organic intermediate which will be formed in each of the reactions given below.

In which reaction does the reactive carbon atom change from being sp3 hybridised to being sp2 hybridised? 1. 2.
CH2CH3 + Cl2 in UV light

C(CH3)2I

+ NaOH (aq), heat

3. 139

CH3

Br2 in the presence of iron

AJC Prelim 2010

Saccharin is an artificial sweetening agent. It can be synthesised from methylbenzene through a series of reactions as shown.
O CH3 CH3 SO2Cl CH3 SO2NH2 CO2H SO2NH2 C NH SO2

saccharin

What types of reactions are involved in the series? 1. condensation 2. electrophilic substitution 3. nucleophilic substitution

AJC Prelim 2010

140 Deuterium, D, is the 2H isotope of hydrogen. Which of the reactions will give an organic product containing deuterium? 1. 2.

3.

CJC Prelim 2010

Compiled by Twig Learning Center (http://www.twig.com.sg)

141

In an aldol condensation, an aldehyde loses its hydrogen atom when a base is added. The intermediate then undergoes nucleophilic addition with another aldehyde molecule. When alcoholic potassium hydroxide is added to ethanal, the following reaction occurs:

142 Fluocortin is a glucocorticoid that is involved in the regulation of glucose metabolism.

What are the possible products when alcoholic potassium hydroxide is added to an equimolar mixture of ethanal and propanal? 1. CH3CH(OH)CH2CHO 2. CH3CH2CH(OH)CH2CHO 3. CH3CH2CH(OH)CH(CH3)CHO CJC Prelim 2010

Fluocortin is first reacted with hydrogen in the presence of a platinum catalyst to obtain a Compound Y. Which of the statements concerning Compound Y are true? 1. Oxidation of Y produces an organic compound that reacts completely with 3 mol of 2,4-dinitrophenylhydrazine 2. It has three chiral centres more than Fluocortin. 3. It can be distinguished from Fluocortin by using sodium carbonate. CJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

143 Methylparaben is used as both a food preservative and a anti-fungal agent in cosmetics.
O HO O CH3

Methylparaben

Which of the statements about methylparaben are correct? 1. It is likely to be more acidic than phenol. 2. It can react with ethanoyl chloride to form an ester. 3. It can react with 2,4-dinitrophenylhydrazine to give an orange precipitate. CJC Prelim 2010 144 Which of the following statements are true regarding compound Z?

1. There is only one sp hybridised carbon atom in a molecule of Z. 2. A molecule of Z contains four bonds. 3. After Z reacts with LiAlH4, all the carbon atoms in the product formed are sp3 hybridised. HCI Prelim 2010 145 The diester R, which is used in perfumes, has the molecular formula C7H12O4. It is found that one of the products of acid hydrolysis of R produces effervescence when heated with acidified KMnO4(aq). Which of the following structures can be compound R? 1. CH3CO2CH2CH2OCOCH2CH3 2. CH3CH2OCOCH2CO2CH2CH3 3. CH3CO2CH2CH2CO2CH2CH3 HCI Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

146

Adrenaline and hydrocortisone are hormones produced by the adrenal glands.

Which of the following reagents are able to distinguish the two hormones? 1. Aqueous neutral FeCl3 2. Hot aqueous potassium dichromate(VI), K2Cr2O7(aq) 3. Aqueous bromine, Br2(aq) HCI Prelim 2010 147 1-bromopropane can be converted to propanone in exactly three steps.

Which of the following reagents can be used in the conversion? 1. Aqueous NaOH 2. Ethanolic NaOH 3. Acidified KMnO4 HCI Prelim 2010 148 Consider the following reaction. (CH3)3SiCl + CH3CH2ONa+ (CH3)3SiOCH2CH3 + Cl

Which of the following statements are likely to be true? 1. The reaction involves a nucleophilic attack by the ethoxide ion. 2. Chlorine is displaced by the ethoxide ion. 3. The carbon-oxygen bond is broken. Compiled by Twig Learning Center (http://www.twig.com.sg)

IJC Prelim 2010

149 A tripeptide, cys-ala-his, was analysed using electrophoresis. The tripeptide was hydrolysed and the resulting solution was added to a buffer solution of pH 6.00 which was then placed at the centre of the plate. A potential difference was then applied across the plate.

Amino acid

cysteine (cys) Isoelectric point 5.05

alanine (ala) 6.00

histidine (his) 7.60

With reference to the above table, which of the following statements are correct? 1. Alanine would remain at the centre of the plate. 2. Cysteine would migrate towards the anode. 3. Histidine would migrate towards the cathode. HCI Prelim 2010 150 Lycra is a polyurethane fibre widely used in sportswear and fashion. A repeat unit of the polymer is shown below. (The values of x and y are usually between 3 and 8.)
H H n O C N (CH2)x N C O (CH2)y

What are the organic products formed when Lycra is heated with aqueous NaOH?
H H HO C N O
(CH2)y OH H

(CH2)x

N C OH O

1. 2. HO 3.

H N

(CH2)x

IJC Prelim 2010

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151

Tert-butyl-bromide can form a Grignard reagent by reacting with magnesium metal.

Because magnesium is more electropositive than carbon, the carbon-magnesium is polarised CMg +.

The Grignard reagent can subsequently react with water as shown in reaction I.

Which of the following statements are correct? 1. Reaction I is an acid-base reaction. 2. The product of reaction I is (CH3)3CH. 3. Carbonyl compounds react with Grignard reagents via nucleophilic addition. IJC Prelim 2010 152 For the following reaction: (CH3)3CSO2Cl + CH3CH2OH (CH3)3CSO3CH2CH3 + HCl Which statements are likely to be true? 1. The CO bond is not broken. 2. Cl is displaced by CH3CH2O . 3. The reaction involves a nucleophile. MJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

153

-aminobutyric acid and -aminobutyric acid are isomers.

Which statements are true? 1. Both are soluble in water. 2. Both can form zwitterions. 3. Both can be obtained from the hydrolysis of protein.

-aminobutyric acid -aminobutyric acid

MJC Prelim 2010

154 The Grignard reaction is a very important tool in organic reactions involving the formation of carbon-carbon bond. Grignard reagents are formed by reacting halogenoalkane, R-X, with magnesium in dry ether. For example, reaction of CH3Cl with Mg,

Grignard reagents allow the carbon chain of carbonyl compounds to be lengthened. For example,

Which compounds could be made from a ketone and a Grignard reagent? 1. CH3C(CH2CH3)2OH 2. CH3CH2CH2CH2OH 3. (CH3CH2)2CHOH MJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

155

Salicylic acid is an important compound in its medicinal and cosmetic uses.

COOH

Salicylic acid

OH

Which compounds give salicylic acid on acid hydrolysis?

1.

2.

3.

MJC Prelim 2010

156 The rod cells in the retina at the back of the eye contain an alcohol called retinol which is responsible for their sensitivity to light. Retinol is oxidised by an enzyme- catalysed reaction to retinal with the following structure:
O

Which of the following statements about retinal are correct? 1. The molecular formula of retinal is C20H28O. 2. It can react with NH2OH.

3. The structure of its cis isomer is

NJC Prelim 2010

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157 The French chemist, Eugene Peligot, discovered that Group II salts of carboxylic acids on heating decompose to give a metal carbonate and a carbonyl compound. An example of such decomposition is as shown: (RCOO)2Ca CaCO3 + R2CO The likely products(s) obtained when a mixture of calcium ethanoate and calcium methanoate is heated are: 1. CH3COCH3 2. CH3CHO 3. HCHO NJC Prelim 2010 158 1. 2. 3. 159 Which mixtures, on heating, produce an alkaline gas containing deuterium, D? CH3CH2CONHCH3 and NaOD in D2O (ND2H2)2SO4 and NaOD in D2O C6H5CH2CN and DCl in D2O

NJC Prelim 2010

Compound A was used in the following synthetic route.

Which statement is true regarding the synthetic route? 1. There are 3 sp3, 6 sp2 and 1 sp hybridized carbon atoms in Compound B. 2. The synthetic route involves addition and reduction reactions. 3. Compound B is optically active. NJC Prelim 2010 160 1. 2. 3. Which of the following reagents will convert nitrobenzene to phenylamine? tin, concentrated hydrochloric acid, followed by aqueous sodium hydroxide hydrogen, nickel catalyst lithium aluminium hydride in dry ether NYJC Prelim 2010

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161

Which of the following pairs illustrate geometric isomerism?

CH3CH2 C C H Br H C H Br H C H Br C CH3 CH3 H C Br Br C C CH2CH3 CH3

1.

2. CH3
H C C

Br C C

NYJC Prelim 2010 162 Salicylic acid is prepared from the Kolbe-Schmitt process. In one of the steps, the phenoxide ion reacts with the weak electrophile, carbon dioxide, to give sodium salicylate as a product.
OH CO2Na

3. CH3

CH3

sodium salicylate Which of the following statements are correct? 1. The phenoxide ion is more reactive towards electrophilic attack than phenol. 2. The phenoxide ion undergoes an electrophilic substitution mechanism. 3. A hydroxyl group makes the benzene ring less susceptible to electrophilic attack. NYJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

163 Which of the following reacts with aqueous bromine to give an organic molecule containing three bromine atoms?
NH2

1.

CH3 NH2

2.
NO2

3. 164

NYJC Prelim 2010

The structures and pKa values of fumaric acid and maleic acid are given below:
HOOC H HOOC H H COOH COOH H

pKa1 3.0

pKa2 4.5

fumaric acid

1.9

maleic acid

Which of the following statements are correct? 1. Maleic acid has a lower boiling point than fumaric acid as it can form intra-molecular hydrogen bonding. 2. pKa2 of maleic acid is larger than that of fumaric acid because the acidic hydrogen atom in maleic acid can be stabilised by intra-molecular hydrogen bonding, hence making it more difficult to remove. 3. For each acid, pKa2 is larger than pKa1 because it is easier to remove a second proton from the conjugate base formed in the first ionisation. RJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

165 Which products are formed when phenyl propanoate undergoes acidic hydrolysis in the presence of water labeled with the 18O isotope? 1. CH3 CH2CO18OH 2. C6H518OH 3. C6H5CO18OH RJC Prelim 2010 166 Consider the following reaction scheme.
CH3CH2SH + CH3CH2S + CH3O CH2 O CH3CH2SCH2CH2OH + OH Which of the following types of reactions are shown in reactions I, II and III? 1. oxidation 2. nucleophilic substitution 3. neutralisation RJC Prelim 2010 CH3CH2SCH2CH2O + H2O III

I II

CH3CH2S

CH3OH

CH2

CH3CH2SCH2CH2O

167 Which of the following pairs of reagents will give a water-soluble organic product when reacted together? 1. CH3CH2COOH and LiAlH4 2. CH3CH2COOH and CH3CH2NH2 3. CH3CH2COCl and (CH3CH2)2NH RVHS Prelim 2010 168 Which statements about the following reaction sequence are correct?
H C H C H H I Br2 in CCl4 X II excess conc NH3 in sealed tube Y III Cu2+(aq) Z

1. Compound X is 1,2-dibromoethane 2. Step II involves nucleophilic substitution 3. Step III involves ligand exchange

TJC Prelim 2010

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169

Propanone and hydrazine can react to form hydrazine derivatives as shown below:
H3C C O + NH2NH2 H3C H3C C NNH2 + H2O

H3C

The reaction involves addition reaction, followed by elimination. Which of the following are possible steps in the reaction?
H3C C O + NH2NH2 H3C
H3C C O + NH2NH2 H3C C NH2NH2 O

H3C C O H + NH2NH-

1.

H3C
H3C

2.

H3C

H3C C

O NH2NH2

H3C C H3C

OH NHNH2

3.

H3C

TJC Prelim 2010

170 Which of the following reactions give products that do not rotate the plane of polarised light? 1. Propene reacted with bromine dissolved in organic solvent. 2. Ethanal reacted with HCN, trace NaOH, 10 20C 3. 3-chloro-3-methylhexane refluxed with aqueous KOH. TJC Prelim 2010 171 When a compound W was heated in the tube containing reagent X, a colour change was observed in the tube. A precipitate was noted when reagent Y was heated with the products from reaction of W and X. Which of the following combinations could be W, X and Y? W CH2=CH2 CH2=CHCH3 CH3CH2Br X aqueous bromine acidified KMnO4(aq) NaOH(aq)

Y 1. CH3CO2-Ag+ 2. Fehlings solution 3. alkaline aqueous iodine TJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

172 The following compound, Z, is a by-product formed in the body that counteracts the effect of the drug administered to patients to treat herpes.
NH H2N N H NH2 O N H O NH2 OH

Which of the following statements about this compound are correct? 1. Z undergo nucleophilic substitution with chloroethane 2. One mole of Z can be hydrolyzed to produce 2 moles of amino acids 3. When an aqueous solution of Z at pH 3 is analysed by electrophoresis, it is found near the anode TJC Prelim 2010 173 Compound Z gives white fumes with PCl5, and releases ammonia gas upon addition of hot aqueous NaOH. Which compounds could be Z? 1. HO2CCH2CH2CN 2. HOCH2CH2CONH2 3. HOCH(CH3)CH2NH2 VJC Prelim 2010 174 Psilocin is a psychedelic mushroom alkaloid which is the active compound that produces hallucinations from ingesting magic mushrooms and amplifies sensory experience. Compound K is a derivative of Psilocin.
OH CH2CH2NHCH3

Which statements are correct for compound K? 1. It gives white fumes with CH3COCl. 2. It reacts with both aqueous acids and alkalis. 3. The nitrogencontaining group in the ring has a lower pKb than the nitrogen containing group in the side chain. VJC Prelim 2010 Compiled by Twig Learning Center (http://www.twig.com.sg)

H compound K

175 In some reactions, the reactive carbon atom is not sp3 hybridised in the reactant molecule but becomes sp3 hybridised in the organic intermediate. To which of the following reactions does this statement apply?

1. 2.

3.

VJC Prelim 2010

176 1.

Which reactions would produce benzene1,3dicarboxylic acid?

CN + aqueous H2SO4, reflux CO2CH3

2. 3.

CH(OH)CH3

+ akaline aqueous iodine followed by acidification

COCH3

VJC Prelim 2010

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