Organic Chem

2012 JC 2 H2 Chemistry Revision Topic 10: Organic Chemistry
MCQ Section A
ACJC/PRELIM 2009/P1/Q23 1 The drug cortisone has the formula shown.
CH 2OH CH 3 O CH 3 CO OH
How many chiral centres are present in the molecule after its reaction with LiAlH4? A 5 B 7 C 9 D 11
SAJC Chemistry Unit 2009
ACJC/PRELIM 2009/P1/Q24 2 Ethene reacts with aqueous bromine to give CH2BrCH2Br and CH2BrCH2OH. Which statement is correct for the above reaction? A B C D Both products can be hydrolysed to form the same diol. Both products are non-polar. Both products are obtained via nucleophilic addition. The dibromo product exhibits optical isomerism.
ACJC/PRELIM 2009/P1/Q25 3 CS, whose structure is shown below, is an active component of tear gas and is readily hydrolysed.
CN CH C CN
Which of the following is a possible hydrolysis product of CS? A

CH 2 H C NC CN
B
CH C
NH 2
NH2
C
CH C
CO2H
CO2H
D
CN
ACJC/PRELIM 2009/P1/Q26 4 The following compound undergoes the given reaction sequence.
CH 2CH 2OH _ + MnO4 / H D heat OH SOCl2 E
Which of the following could be product E? A

COCl
OH
COCl
Cl
CH 2COCl
OH
CH 2COCl
Cl
ACJC/PRELIM 2009/P1/Q27 5 In which sequence is it correctly stated that the value of pKa decreases continuously? A B C D CH3CO2H > CCl3CO2H > C2H5OH > C6H5OH CCl3CO2H > CH3CO2H > C2H5OH > C6H5OH C2H5OH > C6H5OH > CH3CO2H > CCl3CO2H C6H5OH > C2H5OH > CH3CO2H > CCl3CO2H
ACJC/PRELIM 2009/P1/Q28 6 Phenol reacts with diazonium chloride as shown.

Cl - N N OH
OH
+ 0-5 C N N
o
HCl
Which term describes this type of reaction? A B C D electrophilic addition electrophilic substitution free-radical substitution nucleophilic addition
ACJC/PRELIM 2009/P1/Q29 7 In the study of the polypeptide structure of A, it 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 the first enzyme: gly-pro-val ser-pro-gly asp-gly thr-phe-leu Digestion using the second enzyme: val-asp-gly-thr pro-gly phe-leu-ser gly-pro
What is the correct sequence of polypeptide structure of A? A B C D pro-gly-pro-val-asp-gly- thr-phe-leu-ser-pro-gly gly-pro-val- ser-pro-gly- asp-gly- thr-phe-leu gly-pro-val-asp-gly- thr-phe-leu-ser-pro-gly ser-pro-gly-pro-val-asp-gly- thr-phe-leu-ser
ACJC/PRELIM 2009/P1/Q30 8 Which of the following reagents may be used to distinguish between methanoic acid and benzaldehyde? A B C D Tollens reagent 2,4-dinitrophenylhydrazine Lithium aluminium hydride Hydrogen chloride
AJC/PRELIM 2009/P1/Q20 20 The diagram shows the structure of chlolecalciferol, which is a form of vitamin D.
HO
How many chiral carbon atoms are present in this molecule? A 4 B 5 C 6 D 7
AJC/PRELIM 2009/P1/Q21 21 Which of the following gives the largest number of isomers on reacting with hot ethanolic potassium hydroxide? A B C D (CH3)3CCH2Cl CH3CH2CHClCH3 (CH3)2CHCH(CH3)CH2Cl CH3CH2CH(CH3)CH(CH3)Cl
AJC/PRELIM 2009/P1/Q22 22 In the molecule shown below, which carbon atom is most likely to be attacked by a nucleophile?
A
O2N
B Cl H C C H H C CH3 C
AJC/PRELIM 2009/P1/Q23 23 Straight chain alkanes undergo cracking at high temperatures and in the presence of catalyst. Which of the following does not represent a correct cracking reaction? A B C D C10H22 C3H8 + C5H10 + C2H4 C13H28 C4H8 + C6H14 + CH3CH=CH2 C7H16 CH3CH=CH2 + CH(CH3)3 C11H24 C4H10 + CH2=CH2 + C5H10
AJC/PRELIM 2009/P1/Q24 24 The following compound is produced when ethene reacts with bromine in the presence of concentrated aqueous sodium nitrate.
H H C ONO2 H C Br H
Which of the following descriptions about the organic intermediate in this reaction is correct? A B C D It has a negative charge. It is a free radical. It contains carbon, hydrogen and bromine atoms. It contains carbon, hydrogen, oxygen and nitrogen atoms.
AJC/PRELIM 2009/P1/Q25 25 Boranes, such as BH3, are readily added across a carbon-carbon double bond and the resulting product can be oxidised with alkaline H2O2.
CH3 C CH3 C H H + H B H H CH3 CH3 C H CH2 BH2 H2O2 OHCH3 CH3 C H CH2 OH + HO BH2
Which compound is produced when 3-methylpent-2-ene is treated with BH3, followed by alkaline H2O2? A B C D CH3CH2CH(CH3)CH(CH3)OH CH3CH2CH(OH)CH(CH3)2 CH3CH2CH2CH(CH3)2OH (CH3CH2)2C(CH3)OH
AJC/PRELIM 2009/P1/Q26 26 Which of the following salts would produce the most alkaline solution when dissolved in water? A B C D C6H5O-Na+ C2H5O-Na+ C2H5CO2-Na+ C2H5NH3+Cl-
AJC/PRELIM 2009/P1/Q27 27 Which procedure gives the best yield of phenylbenzoate, C6H5CO2C6H5? A B C D Reacting C6H5CO2H with SOCl2, then adding C6H5OH. Reacting C6H5OH with NaOH, then adding C6H5COCl. Refluxing a mixture C6H5CO2H and C6H5OH with concentrated H2SO4. Reacting C6H5OH with SOCl2, then adding C6H5CO2H.
AJC/PRELIM 2009/P1/Q28 28 When an organic compound L was treated with phosphorous pentachloride, fumes of hydrogen chloride were evolved. When L was warmed with Fehlings solution, a brick-red precipitate was obtained. Which of the following is likely to be compound L?
HO
CH2COCH3
HO
CH2CHO
C D
CH(OH)CH2CHO
CO2CH2CH2OH
AJC/PRELIM 2009/P1/Q29 29 Silk fibroin is a type of fibrous protein made up almost entirely of pleated sheets. The main amino acids found in silk fibroin are alanine, glycine, serine and cysteine. The structures of these amino acids are given below.
H2N CH H glycine COOH H2N CH CH3 alanine COOH H2N CH COOH H2N CH COOH
CH2OH serine
CH2SH cysteine
Which of the following statements about the type of interactions present in silk fibroin is not correct? A B C D The pleated sheets are held together by hydrogen bonding. There are van der Waals forces between glycine and alanine in the protein. There are disulphide linkages present in silk fibroin. Serine forms ionic bonds with another serine amino acid in the protein.
AJC/PRELIM 2009/P1/Q30 30 How many different tripeptides can be produced from the partial hydrolysis of the following octapeptide (eight amino acid residues)? Gly Leu Asp Asp Leu Gly Leu Asp
IJC/PRELIM 2009/P1/Q14 14 When the molecule below is heated with hydrogen gas in the presence of nickel catalyst, how many chiral centres does the product molecule possess?
CH3 CH2OH COOH O CH3 CH(CH3)2
A B
5 7
C D
6 8
IJC/PRELIM 2009/P1/Q15 15 Which of the following reagents could not be used to distinguish between compound X and Y?
A B
I2 in NaOH (aq) PCl5
C D
Cu2+ in alkaline solution acidified potassium dichromate
IJC/PRELIM 2009/P1/Q16 16 Compound Q has the following properties. (i) It produces white fumes when PCl5 is added. (ii) It does not react with Na2CO3 but forms a soluble salt in aqueous NaOH. (iii) It gives an orange precipitate with 2,4dinitrophenylhydrazine. Which one of the following could be Q?
COCH3 OH
COOH
CH2COCH3
OH CH2OH
COOCH3 CH2CH2OH
CH2CH2CHO
10
IJC/PRELIM 2009/P1/Q17
17
Wedelolactone, the naturally occurring active ingredient of herbal medicine and has been extensively used in South American native medicine as snake antivenom.
Which of the following is true about Wedelolactone? A B C D It can react with 5 moles of aqueous bromine. It gives an orange precipitate with 2,4-dinitrophenylhydrazine. It is resistant to hydrolysis in both acidic and alkaline medium. It results in the formation of green Cr3+ ions from an acidified solution of Cr2O72- ions.
18
Which reaction scheme proposed will most likely lead to a successful reaction giving the products given? A
11
19
Concentrated ammonia was heated in a sealed tube with excess bromoethane, C2H5Br. Which of the following products will not be formed? A B C D C4H11N C5H13N C6H15N C8H20NBr
20
0.01 mol of compound R is refluxed with 50 cm3 of 1 mol dm-3 aqueous NaOH and all ammonia gas evolved is expelled. The resulting solution is subsequently titrated with 1 mol dm-3 H2SO4 solution.
What is the volume of H2SO4 required for complete neutralisation of the resulting solution? A B 10 cm3 20 cm3 C D 30 cm3 40 cm3
12
21
Which compound can be synthesized from prop-1-ene in less than 3 steps? A

H H C H H C CH3
OH H C C H
H N
O C
H C H H
C
H
H C H
O C
O C OH
B
H
H C H
D
H
H C H
H C
H C
H N H
CN H
CH3 H
22
In the presence of a base, some aldehyde and ketone undergo a rapid and reversible condensation reaction, where they dimerise to form a hydroxycarbonyl compound (an aldol).
This reaction is initiated by the production of the enolate ion, RCOCH 2, formed from the reaction between a carbonyl molecule and a base. What is the mechanism involved in the above reaction? A B Electrophilic addition Electrophilic substitution C D Nucleophilic addition Nucleophilic substitution
13
23
A mixture of amino acids can be separated by electrophoresis.
Mixture of filter paper amino acids
The following information about alanine and two other amino acids are given as below. Amino acid Structure
H
Isoelectric point
alanine (ala)
H2N
C CH3
COOH
6.01
glutamine (gln)
H2N
COOH
5.65
CH2CH2CONH2
lysine (lys)
H2N
COOH
9.74
(CH2)4NH2
Which of the following filter papers show a possible result of the separation of the amino acid mixture at pH 8?
14
A
anode cathode
lys
gln ala
B
anode cathode
ala gln
lys
C
anode cathode
lys
ala gln
D
anode cathode
gln ala
lys
24
In which of the following sequences does the value of pKa increase continuously? A B C D CH3CHClCOOH, CH3CH2COOH, C6H5OH CH2ClCH2COOH, CH3CHClCOOH, CH3CH2COOH C6H5OH, CH3CHClCOOH, CH3CHFCOOH CH3CH2COOH, CH3CHFCOOH, CH3CF2COOH
15
25
Enols, also known as alkenols, are alkenes with a hydroxyl group affixed to one of the carbon atoms composing the double bond. Enols and carbonyl compounds are rapidly interconvertible via a process called tautomerism.
O C H rapid equilibration C O C C H
enol
carbonyl compound
The enol form is usually unstable and difficult to isolate and are present only to a very small extent at equilibrium. Propane-1,2-diol can undergo dehydration with excess concentrated H 2SO4 to give enols and a mixture of products. Which of the following is false about the resulting solution? A B C D It decolourises hot acidified potassium manganate (VII) solution with the evolution of a colourless gas. It gives a yellow precipitate with aqueous alkaline iodine. It gives a grey precipitate with silver diammine complex. It reacts with cold alkaline potassium manganate (VII) solution to give an optically active product.
26
Which of the following statements is false? A B C D Denaturation does not affect the primary structure of proteins which implies that there is no breakage of the peptide bonds. In an alpha helix, the amide carbonyl oxygen of an amino acid residue n is hydrogen bonded to the amide hydrogen of residue n+4. The formation of the peptide link between amino acids is irreversible. The quaternary structure only applies to proteins that contain two or more polypeptide chains.
16
CJC/PRELIM 2009/P1/Q19 Athletes preparing for the Youth Olympics Games (YOG) in 2010 follow a highcarbohydrate diet to maintain high-intensity exercise for a longer period. Glucose is an important carbohydrate in biology as the living cell uses it as a source of energy and metabolic intermediate.
glucose How many stereoisomers does glucose exhibit? A 21 B 22 C 23 D 24
CJC/PRELIM 2009/P1/Q20 20 The equation below represents the sulfonation of benzene under suitable conditions. + H2SO4 SO3H + H2O
What is the role of concentrated sulfuric acid in the reaction? A a dehydrating agent C a nucleophilic agent B an electrophilic agent D an oxidising agent
CJC/PRELIM 2009/P1/Q21 21 Chlorofluorocarbons, commonly known as CFCs, undergo homolytic fission by ultraviolet irradiation in the stratosphere. Which radical could result from this irradiation of CHFClCF2Cl? A CHFClCFCl B CHClCF2Cl C CHFCF2Cl D CFClCF2Cl
17
CJC/PRELIM 2009/P1/Q22 22 A product P, isolated from a naturally-occurring source, has a molecular formula of C9H11NO3. It possesses a chiral centre and it forms a zwitterion. What could the structure of P be? O2N CH2CH(OH)CH3
HO
CH2CH(NH2)CO2H
HO2C
CH2CH2NH2
CH3
CH2CO2H
CJC/PRELIM 2009/P1/Q23 23 Which of the following compounds is not an addition product of the reaction between ethene with aqueous chlorine in the presence of sodium bromide?
H Cl C H H Cl C H
B H
Cl H H OH
Br H H OH H
C Br
C H
D H
C Cl
C H
CJC/PRELIM 2009/P1/Q24 24 Which of the following compounds could be prepared by reacting chloropropane with potassium cyanide and then reducing the product? A CH3CH2CH3 B CH3CH2CH2NH2 C CH3CH2CH2CH3 D CH3CH2CH2CH2NH2
18
CJC/PRELIM 2009/P1/Q25 25 In the preparation of ethene, ethanol is added a drop at a time to heated reagent Y. The impure ethene is washed by being bubbled through a solution Z and then collected. What are the reagent Y and solution Z likely to be? reagent Y A B C D acidified K2Cr2O7 acidified K2Cr2O7 concentrated H2SO4 concentrated H2SO4 solution Z dilute NaOH dilute H2SO4 dilute NaOH dilute H2SO4
CJC/PRELIM 2009/P1/Q26 26 The following reaction scheme shows the formation of compound C. NCCH2CHClCH2 Cl What is the structure of compound C? NCCH2CH(OH)CH2 Cl B NCCH2CHClCH2 OH C ClOCCH2CHClCH2 Cl D ClOCCH2CH(OH)CH2 OH CH2CONH2 CH2COCl CH2CONH2 CH2CONH2
NaOH(aq) heat 1. H (aq)
+
2. PCl5
NaOH(aq)
CH2COCl
19
CJC/PRELIM 2009/P1/Q27 27 Which of the following reagents will give similar results for both butanone and ethanol? A acidified aqueous potassium dichromate(VI) B iodine and aqueous potassium hydroxide C Fehlings solution D 2,4-dinitrophenylhydrazine reagent CJC/PRELIM 2009/P1/Q28 28 Which of the following reagents is least likely to react with vitamin C?
HO O O
Vitamin C
OH
OH OH
A 2,4-DNPH B Na metal C SOCl2 D Br2(aq)
CJC/PRELIM 2009/P1/Q29 29 Which of the following could be a correct synthesis of aspirin, as shown below?
CO2H OCOCH3
aspirin A
20
CO2CH3 OCOCH3 NaOH(aq)
CO2Na OCOCH3 HCl(aq)
CO2H OCOCH3
reflux
B
CO2H OH CO2H
CH3COCl
OCOCH3
+ HCl
C
CO2H OH CO2H OCOCH3
+ CH3OH
conc H2SO4 reflux
+ H2O
D
CN OCOCH3 NaOH(aq) CO2Na OCOCH3 HCl(aq) CO2H OCOCH3
reflux
21
CJC/PRELIM 2009/P1/Q30 30 A useful oxidising agent specifically for vicinal diols (ie. the two OH groups are on adjacent carbons) used in the laboratory includes NaIO4. An example of the conversion using butane-2,3-diol is shown below:
OH OH NaIO4 CH3 C H C H CH3 2 CH3 C H O
What would be the final organic products obtained when compound Y is first treated with cold alkaline aqueous KMnO4 followed by NaIO4? Compound Y is CH3CH=C(CH3)CH2CH=CH(CH3)
O O O C CH3 CH2 C H
CH3
C H
O C CH2 C H
CH3
C H
OH
OH CH2 C H H
C CH 3
C H
C CH3
OH C CH2 C H H
CH3
C H
22
23
JJC/PRELIM 2009/P1/Q20 20. The structure of compound X is given below.
Compound X How many new chiral centers will be formed when Compound X is completely hydrogenated over a nickel catalyst?
A B C D
2 3 6 7
JJC/PRELIM 2009/P1/Q21 21. When ethene reacts with bromine in the presence of concentrated aqueous sodium nitrate, one of the products formed is given below.
H H C ONO2
H C H
Br
What is the intermediate formed in this reaction?
A
H H C H C Br H
C H H C ONO2 H C H
24
B
H
H C ONO2
H D H H C
H
C
C +
Br
JJC/PRELIM 2009/P1/Q22 22. How many isomers (both structural and stereoisomers) are possible for an aromatic compound of molecular formula C8H7Cl?
A
B C D
4 5 6 7
JJC/PRELIM 2009/P1/Q23 23. Bromine-containing organic compounds, X, Y and Z, are added to aqueous silver nitrate. The mass of cream precipitate formed is measured after some time.
Compound X Y Z
Mass / g 0 0.15 1.05
Which of the following gives the correct structures for X, Y and Z? X BrCH2CH2Br C6H5Br C6H5Br BrCH2CH2COBr Y C6H5Br BrCH2CH2COBr BrCH2CH2Br BrCH2CH2Br Z BrCH2CH2COBr BrCH2CH2Br BrCH2CH2COBr C6H5Br
A B C D
25
JJC/PRELIM 2009/P1/Q24 24. Which compound reacts with 2 moles of aqueous sodium hydroxide at room temperature? A OH B OH COOH OH COOH HCOO CH2OH C D
HCOO
CH2Br
OH
CH2OH
CH2OH
JJC/PRELIM 2009/P1/Q25 25. Compound X, C6H12O, is oxidised by acidified sodium dichromate(VI) to compound Y. Compound Y reacts with ethanol in the presence of a little concentrated sulphuric acid to give liquid Z. What is the formula of Z?
A
B C D
CH3(CH2)2CH=CHCO2H CH3(CH2)4CH2COCH2CH3 CH3(CH2)4CO2CH2CH3 CH3CH2CO2(CH2)4CH3
JJC/PRELIM 2009/P1/Q26 26. The anti-bacterial drug tetracycline has the formula
tetracycline
26
Which statement about tetracycline is correct?
A
B C D
It does not react with SOCl2. It reacts with sodium carbonate to liberate carbon dioxide gas. 3 moles of HBr is formed when 1 mole of tetracycline reacts in an excess of aqueous bromine in the dark. It reacts with sodium metal to liberate H2 gas.
JJC/PRELIM 2009/P1/Q27 27. A nitrile X undergoes the following two reactions:
Nitrile X reduction acid hydrolysis
Product, CH3CH2NH2
Product
What would be produced when the products from the two reactions are mixed together?
A
B C D
[ CH3CH2NH3+ ] [CH3CH2CO2 ]
[ CH3CH2NH3+ ] [CH3CO2 ] CH3CONHCH2CH3 CH3CH2CONHCH2CH3
27
JJC/PRELIM 2009/P1/Q28 28. Compound Q was subjected to the following tests and the results are recorded below.
Reagents & Conditions Acidified KMnO4, heat Fehlings reagent, heat Tollens reagent, heat What could Q be? A CHO B COCH3
Observations Solution turns from purple to colourless. A gas is evolved. No precipitate observed Silver mirror observed
C CO2H
D CH2CHO
CH=CH2
CH2OH
OH
JJC/PRELIM 2009/P1/Q29 29. The structures of P, Q and R are shown below. CH2COOH CHClCOOH CHFCOOH
When equal amounts of P, Q and R (not necessarily in that order) are added to separate portions of water, solutions with pH values of 2.5, 3.0 and 3.5 are formed. Deduce which pH value is associated with each of the compounds P, Q and R. pH 2.5 A B C D Q P R R pH 3.0 P Q Q P pH 3.5 R R P Q
28
JJC/PRELIM 2009/P1/Q30 30. Gastrins are heptadecapeptide (17 amino acid units) hormones that stimulate the secretion of gastric acid in the stomach of mammals. On hydrolysis of gastrins, the following four peptide fragments were isolated. gly-trp leu-glu-glu-glu-glu-ala-ala-try glu-gly-pro-trp met-asp-phe C-terminus analysis of the heptatdecapeptide yields a phe residue while N-terminus analysis yields a glu residue. Based on the information above, suggest a primary structure for the heptatdecapeptide and the number of peptide bonds it contains. Primary Structure A B C D glu-gly-pro-trp-gly-trp-leu-glu-glu-glu-glu-ala-ala-try-met-asp-phe glu-gly-pro-trp-gly-trp-leu-glu-glu-glu-glu-ala-ala-try-met-asp-phe phe-asp-met-gly-trp-leu-glu-glu-glu-glu-ala-ala-try-trp-pro-gly-glu phe-asp-met-gly-trp-leu-glu-glu-glu-glu-ala-ala-try-trp-pro-gly-glu No. of peptide bonds 17 16 16 17
22
Compound P is optically active.

CH3 Cl O HO
How many chiral centre(s) does compound P have? A B C D 1 2 3 4
29
DHS/PRELIM 2009/P1/Q23
23
A student attempts to synthesise compound S from the following synthetic route.
1. Br2/H2O 2. KCN, base

CN
H2/Ni
Which of the following could be compound S that is formed in this reaction?
CN
CH2NH2
CN
CH 2NH 2
24
An alcohol X, when treated with hot acidified aqueous potassium manganate(VII), gives a final oxidation product which reacts positively to the tri-iodomethane (iodoform) reaction. Which one of the following formula could be X?
30
A
OH
B C D 25
C2H5OH CH3CH(OH)C2H5 C6H5CH(OH)C2H5
Which one of the following represents the organic ion produced when an excess of hot aqueous sodium hydroxide is added to compound R?
ClH2C OCOCH 3 COOCH 3
R
A
HOH2C
O COO
-
O H2C
OH COO
-
C
HOH2C O
-
COO
O H2 C OH
COO
26
Which one of the following, in alcoholic solution, produces a precipitate most rapidly when warmed with aqueous silver nitrate? A B C D chlorobenzene 1-iodobutane 1-bromobutane 1-chlorobutane
31
27
What is the total number of possible stereoisomers that can be formed when the following compound reacts with excess concentrated H2SO4?
HO Cl
OH
A B C D 28
2 4 6 8
Compound Q is subjected to the following tests and the results are recorded below. reagents and conditions acidified KMnO4 and reflux Fehlings reagent and warm Tollens reagent and warm observations Purple solution turns colourless. Effervescence of colourless gas. No precipitate seen. Silver mirror is formed.
Which of the following could be compound Q? A

CHO
CH3
CHCH 2
32
COOH
O H
CH 2OH
OH
29
The reduction of a nitrile produces a compound of formula C3H7NH2. Which of the following would be produced if the same nitrile is heated with hydrochloric acid? A B C D CH3CONH2 CH3CH2OH CH3CH2COOH (CH3)2CHCOOH
30
Separation of benzene from a mixture of benzene and an organic amine could involve A B C D Treating the mixture with dilute aqueous alkali. Treating the mixture with dilute aqueous acid. Extracting the amine with cyclohexanol. Extracting the benzene with diethyl ether (CH3CH2OCH2CH3).
HCI/PRELIM 2009/P1/Q21
21
Spironolactone is an anti-androgen used as a common component in hormone therapy.
33
O H3C CH3 O
O H3C O
How many stereoisomers does spironolactone have? A 23 B 24 C 26 D 27
22
Which of the following compounds will not be produced when propene reacts with a mixture of Br2 in aqueous NaCl?
H H C Br H
H C Cl
H C Br H
H3C
C Br
H3C
C Br
H
H C Cl H
H3C
C Cl
H3C
C Cl
23
During electrophilic substitution on a benzene ring, the position of the incoming group, the new substituent, is determined by the nature of the group(s) already present in the ring. The directing effects of these groups are shown in the table below. Directing Effects Functional Groups with these effects 3 directing NO2, CO2H, 2,4 directing CH3, NH2, X (halogens)
Compound V may be synthesised from benzene.

Br HO2C NH2
34
V Which of the following synthetic routes will yield compound V? A B C D Nitration alkylation reduction bromination oxidation Alkylation nitration oxidation bromination reduction Bromination nitration reduction alkylation oxidation Nitration reduction bromination alkylation oxidation
24
The table below shows the rate of hydrolysis of the halogen-containing compounds P to S. The rate of hydrolysis is measured by the speed at which the silver halide precipitate is formed. P
Cl
Q
CH2Cl
R
CH2Br
S
CH2I
No precipitate formed with prolonged heating with ethanolic AgNO3.
Precipitate formed after 10 minutes of heating reaction mixture with ethanolic AgNO3.
Precipitate formed after 2 minutes of warming reaction mixture with ethanolic AgNO3.
Precipitate forms instantaneously with ethanolic AgNO3.
Which statement explains the rate of reaction? A B C D The CX bond length increases from compound P to S. The solubility of the compounds increases from P to S. The mechanism for the reaction changes from P to S. The reaction conditions are increasingly milder from P to S.
25
Which of the following deductions about the reactions of G can be made from its structure?
35
OH
CH3 O O
A B C D
It gives white fumes of HCl with PCl5. It gives a yellow precipitate with aqueous alkaline iodine. It gives an orange precipitate with 2,4-dinitrophenylhydrazine. It gives a violet colouration with neutral FeCl3 solution.
26
Which of the isomers of C6H14O2 gives, on complete dehydration, the greatest number of isomers, including stereoisomers?
OH OH CH CH2 CH3
CH3
CH2
CH
OH
OH C CH3
OH CH2 CH CH2 CH3
CH3
C CH3
OH
CH3
CH3
CH
OH
OH CH2 CH2 CH CH3
CH3
CH
27
A compound U has all the following properties: - It is neutral. - It gives a silver mirror with Tollens' reagent. 36
- It decolourises a hot aqueous solution of acidified KMnO 4 with evolution of CO2 gas. What could U be? A
COCH3
CHO
OCH3 C O
CH(OH)CH3
CH(OH)CH3
OCH3
CH2CHO
OH
28
Which reaction yields a carbon compound incorporating deuterium, D? [D = 2H] A B C D

CH3CH2CN
CH3CD2OH
CH3COCH3
NaOD D2O acidified KMnO4

heat LiAlD4
dry ether conc. D2SO4
(CH3)3COH
heat
29
The sesquiterpene lactone, M, extracted from sunflowers, was studied to determine its anti-tumour potency.
CH3CO2 CH3 O O O NH CH2 N O CH3
37
M How many moles of dilute NaOH are required to completely hydrolyse 1 mole of M? A 3 B 4 C 5 D 6
30
A student attempted to synthesize the following compound N.

NHCOCH3
OCOCH3
N Which of the following pairs of reactants will give the target molecule?
COCl
NH2
and CH3NH2
OH
and CH3CO2H
OH
NH2
NH2
B
OH
and CH3COCl
and CH3COCl
CO2H
MI/PRELIM 2009/P1/Q23 The compound CF3CHBrCl is a general anaesthetic called halothane. The number of structural isomers, including halothane, having the molecular formula C2HBrClF3 is A 2 B 3 C 4 D 5
MI/PRELIM 2009/P1/Q24 Which one of the following sequences of nitration, alkylation and bromination is expected to give the best yield for the synthesis of 2bromo4nitromethylbenzene from benzene? A B C D Alkylation, nitration, bromination Alkylation, bromination, nitration Nitration, alkylation, bromination Nitration, bromination, alkylation
MI/PRELIM 2009/P1/Q25 The structure below shows the active ingredient of a certain drug.
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Which one of the following statements is FALSE about this compound? A B C D It has 4 stereoisomers. It gives white fumes with PCl5. One molecule of this compound reacts with 3 molecules of bromine. Complete hydrolysis of this compound gives CH3NH2 as one of the product.
MI/PRELIM 2009/P1/Q26 Which one of the statements about the following ester is correct?
A B C D
It is a chain isomer of pentanoic acid. It is a functional group isomer of ethyl propanoate. It can be hydrolysed to produce an alcohol that is resistant to oxidation by acidified potassium dichromate(VI). It can be hydrolysed to produce an alcohol that can also be formed by the acid-catalysed hydration of propene.
MI/PRELIM 2009/P1/Q27 Which one of the following is formed when an excess of bromomethane reacts with diethylamine?
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MI/PRELIM 2009/P1/Q28 A sequence of reactions is shown below.
A correct list of substances for the sequence is Reaction 1 A B C CH3COCl AlCl3 AlCl3 Reaction 2 NaBH4 HCl NaBH4 Reaction 3 Conc. H2SO4 NaOH Conc. H2SO4 Reaction 4 Cl2 Cl2 HCl
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AlCl3
NaBH4
Conc. H2SO4
Cl2
MI/PRELIM 2009/P1/Q29 One industrial preparation of ethanoic acid is direct carbonylation of methanol, using a rhodium catalyst. CH3OH +CO CH3CO2H
CO2H
rhodium
Which compound could be expected to produce
HC
CH2by this method? CO2H
CH2CO2H
OH
A
CH2OH
HC
CO2H
HC
CH2CO2H
CO2H
CH2CO2H
OH
C
OH CH2CO2H
D
HC
HC
CH2CO2H
CO2H
CH2OH
MI/PRELIM 2009/P1/Q30 Gastrins are hexadecapeptide (16 amino acid units) hormones that stimulate the secretion of gastric acid in the stomach of mammals. On hydrolysis of gastrins, the following four peptide fragments were isolated. H2NglytrpCO2H H2NleuglugluglualaalatryCO2H H2NgluglyprotrpCO2H H2NmetasppheCO2H Cterminus analysis of the hexadecapeptide yields a phe residue while N terminus analysis yields a glu residue. Based on the information above, suggest a primary structure for the hexadecapeptide and the number of peptide bonds it contains. No. of peptide bonds 15 15 16 16
Primary structure A B C D H2Nglu-gly-pro-trp-trp-gly-leu-glu-glu-glu-ala-ala-try-met-asp-pheCO2H H2Nglu-gly-pro-trp-gly-trp-leu-glu-glu-glu-ala-ala-try-met-asp-pheCO2H H2Nglu-gly-pro-trp-gly-trp-leu-glu-glu-glu-ala-ala-try-met-asp-pheCO2H H2Nphe-asp-met-try-ala-ala-glu-glu-glu-leu-trp-gly-trp-pro-gly-gluCO2H
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NJC/PRELIM2009/P1/Q18 How many isomeric carbonyl compounds with molecular formula C5H10O are there? A B C D 7 8 9 10
NJC/PRELIM2009/P1/Q19 Trichloroethene is widely used as dry-cleaning agent.

Cl H Cl Cl
Trichloroethene Which of the following does trichloroethene react with to give a chiral product? A B C D Br2 HCl NaOH NaCN
NJC/PRELIM2009/P1/Q20 The oxo-reaction is an important industrial process in which an alkene combines directly with carbon monoxide and hydrogen under suitable conditions. The reaction with ethene is shown below. CH2=CH2 + CO + H2 Catalyst High T, p CH3CH2CHO
Which of the following structural formula correctly represents the product of the oxo-reaction starting with but-2-ene ? A B C D CH3CH2CH(CH3)CHO CH3CH2CH2CH2CHO CH3CH2COCH2CH3 CH3COCH2CH2CH3
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NJC/PRELIM2009/P1/Q21 Which is the major product for the following reaction?
CH3 NO2 + AlCl3 + Cl2
A
CH3 NO2 Cl
CH3 NO2
Cl
CH3 NO2 Cl
CH2Cl NO2
NJC/PRELIM2009/P1/Q22 Which of the following will not be produced when 1-chloropropane is heated in ethanolic sodium hydroxide? A B C D CH3CH=CH2 CH3CH2CH2OH CH3CH2CH2ONa CH3CH2CH2OCH2CH3
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NJC/PRELIM2009/P1/Q23 Which sequence correctly represents the compounds in the order of increasing pKa values? A
Cl C OH H CH3 OH Cl OH
B
OH CH3
Cl C OH H Cl
Cl OH Cl OH CH3 C OH H
OH
D
OH Cl
Cl C OH H OH CH3
NJC/PRELIM2009/P1/Q24 How many chiral centres are present in the major product formed when compound S undergoes a reaction with KBr and concentrated H2SO4 at high temperature?
H 3C CH3
HO CH3
S A B C D 6 7 8 9
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NJC/PRELIM2009/P1/Q25 Compound P is used in the following synthesis.

CH2OH COCH2CH2OH excess conc. H2SO4 Q D heat Br2(aq) E R
P What is the likely structure of the final product R? A

Br CH2OH COCHOHCH2Br COCH(OH)CH2Br
C
CH2OH COCHBrCH3
Br
CH2OH COCHBrCH2Br
D
CH2OH COCHOHCH2Br COCH(OH)CH2Br
Br
NJC/PRELIM2009/P1/Q26 Compound N is a product formed from the reaction between an alcohol and hot acidified potassium manganate(VII). Compound N gives no yellow precipitate with alkaline iodine evolves a colourless gas when treated with aqueous sodium carbonate reacts with 2 moles of PCl5 to give white fumes What is the structural formula of the alcohol? A B C D CH3COCH2CH2COOH CH3CH(OH)CH2CH2CH2OH (CH3)2C(OH)CH2COOH (CH3)2C(OH)CH2CH2OH
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NJC/PRELIM2009/P1/Q27 The mechanism below shows how butanone reacts with hydrogen cyanide.
CH2CH3 + C H3C O + CNslow H3C CH2CH3 C CN O-
CH2CH3 H3C C CN O+ + H CN H3C
CH2CH3 C CN OH + CN-
Which statement is true? A B C D The product mixture is optically active. Rate of reaction increases when butanone is substituted with butanal. Cyanohydrin produced can react with ammonia at high pressure to form amine. Cyanohydrin produced requires potassium manganate(VII) to form carboxylic acid .
NJC/PRELIM2009/P1/Q28 Phenylalanine is used to synthesize compound M during the production of a drug. Which of the following can be used to identify the phenylalanine from compound M?
NH2 CH2CHCOOH NH2 CH2CHCHCOOH OH
Phenylalanine A B C D Sodium metal Phosphorus pentachloride Aqueous sodium carbonate Hot acidified potassium dichromate(VI)
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NJC/PRELIM2009/P1/Q29 Which synthetic route will lead to a successful synthesis of the following product?
COOH
CH2CH2CH3
CHO
CH2=CHCH2Cl AlCl3
CHO
LiAlH4 in dry ether
CH2OH
K2Cr2O7 dilute H2SO4 heat
COOH
CH2CH=CH2
CH2CH2CH3
CH2CH2CH3
CHO
CH2=CHCH2Cl AlCl3
CHO
LiAlH4 in dry ether
CH2OH
KMnO4 dilute H2SO4 heat
COOH
CH2CH=CH2
CH2CH2CH3
CH2OH
CH2CH2CH3
COOH
CHO
CH2=CHCH2Cl AlCl3
CHO
H2 / Pt
KMnO4 dilute H2SO4 heat
CH2CH=CH2
CH2CH2CH3 CH2OH
CH2CH2CH3 COOH
CHO
CH2=CHCH2Cl AlCl3
CHO
H2 / Pt
K2Cr2O7 dilute H2SO4 heat
CH2CH=CH2
CH2CH2CH3
CH2CH2CH3
NJC/PRELIM2009/P1/Q30 Electrophoresis is a technique of separating and identifying amino acids. A solution of amino acids is absorbed into paper that is moistened with a buffer solution and stretched between two electrodes. Positively charged species move towards the cathode, negatively charged species towards the anode. With a buffer at pH 4, which amino acid will move most readily towards the cathode? A
O OH HO NH2
C
O
NH2
O OH NH2
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B
N N H
O OH NH2
D
HO
O OH NH2
NYJC/PRELIM2009/P1/Q21
The following statements were made about the structure and functional groups of compound P
OH HO CH(OH)CH 2OH
Compound P I. II. III. It has cis-trans isomers It is optically active It has three chiral centres
Which of the above statement(s) about compound P is/are correct? A B C D I, II and III I and II only II and III only II only
Which of the following isomers of C5H11Br gives the greatest number of different alkenes on treatment with hot ethanolic sodium hydroxide? A B C D CH3CH2CH(CH3)CH2Br CH3CH2CH2CHBrCH3 CH3CH2CHBrCH2CH3 CH3CH(CH3)CH2CH2Br
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Which one of the following reagents will distinguish X and Y?

CH3 O O CH3 O HO O CH3 CH2OH C O OH
HO
X A B C D aqueous bromine Fehlings reagent phosphorus pentachloride alkaline aqueous iodine
Vanillin is the main constituent of vanilla flavouring.

OH OCH3
CHO
What is the product of its reaction with KMnO4 in aqueous KOH? A

OK
- +
B
OCH3
OK
- +
OCH3
CO 2 K
COOH
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OH OCH3
OK
- +
OCH3
COOH
CHO
The 1st stage of the cumene process for the industrial production of phenol is as follows:
H3C CH CH3
H2 SO4
H3C CH CH2
Which one of the following would be the product of the reaction under similar conditions between benzene and cyclohexene? A B C
CH2(CH 2)4CH3
D
CH CH(CH 2)3CH 3
The reddish brown colour of aqueous bromine is discharged when a solution of phenylamine is added to it. Which statement explains this observation? A B C D Bromine displaces hydrogen in the benzene ring The NH2 group of phenylamine is substituted by bromine Bromine forms a colourless complex with phenylamine Phenylamine oxidizes Br2 to Br
-
Which one of the following is a product of the reaction between phenylmethanol, and ethanoyl chloride, CH3COCl ?
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A
OCOCH3
B
CH2OCOCH3
C
COOCH2CH3
D
CH2COOCH3
One industrial preparation of ethanoic acid is the direct carbonylation of methanol using a rhodium catalyst
CH3OH
rhodium
CO CH3 C
OH O
CO 2H HC CH 2CO 2H
catalyst
Which compound could be expected to produce CH 2CO 2H A

OH HC CO 2H
CH 2OH
CH 2OH HC CH 2CO 2H
CH 2CO 2H
OH HC CH 2CO 2H
CO 2H
OH HC CH 2CO 2H
CH 2OH
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It has been reported that some cases of acute liver failure could have been caused by an overdose of Paracetamol. Which of the following statements about Paracetemol is incorrect?
CH3 NH C O
HO
Paracetemol
A It reacts with hot, aqueous sodium hydroxide to give sodium ethanoate B There is no yellow precipitate observed on adding aqueous, alkaline iodine C The colourless gas evolved on adding sodium metal extinguished a lighted splinter with a pop sound. D An aqueous solution of Paracetamol is alkaline
What is the order of increasing pKb for the following compounds?

NH2 NH2 NHCH3 NH2
NO2
II
III
IV
A B C D
II, I, III, IV IV, III, I, II III, IV, II, I III, IV, I, II 52
PJC/PRELIM2009/P1/Q21
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54
55
56
57
58
59
RIJC/PRELIM2009/P1/Q19
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61
62
63
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SAJC/PRELIM2009/P1/Q23 Which of the following pairs of compounds can be attacked by cyanide ions via nucleophilic reactions? A B C D CH3CH2Cl and CH3COCH2CH3 CH3CH2Cl and CH3COOCH3 C6H5Cl and CH3COCH2CH3 C6H5Cl and CH3COOCH3
SAJC/PRELIM2009/P1/Q24 Acarol is the active ingredient in many insecticides.

O HO C Br Acarol C O C(CH3)3
Br
Which of the following statements about Acarol is true? A B C D Acarol exhibits stereoisomerism. Acarol forms white fumes with thionyl chloride. Acarol changes hot, acidified K2Cr2O7 from orange to green. Acarol forms an orange precipitate with 2,4 dinitrophenylhydrazine.
SAJC/PRELIM2009/P1/Q25 Cannabis is a psychoactive drug which accumulates in the fatty tissues of the body. Compound W can be prepared from cannabis as shown in the following reaction sequence.
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HO CH3 OH
(CH2)4CH3 CH3 Step I
(CH2)4CH3
OC CH3 H2 C
C CH3 H2C
Cannabis
Step II
HOOC(CH2)2O CH3
(CH2)4CH3
O(CH2)2COOH C CH3 H2C
W
Which of the following reagents can be used to prepare compound W?
Step I A B C D Na2CO3 NaOH Na NaOH
Step II CH2(OH)CH2COOH CH2ClCH2COOH CH2(OH)CH2CH2COOH CH2ClCH2CH2COOH
SAJC/PRELIM2009/P1/Q26 When propene reacts with Br2 in the presence of excess aqueous KNO3, what are the two major products formed?
H H H
A
H H H and H C C C H H OH Br H H H and H C C C H H OH Br
H C C C H H Br Br H H H
H C C C H H H Br
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H H H
C
H H H and H C C C H H Br OH
H C C C H H Br H
H H H H C C C H
D
H H H and H C C C H H OH Br
Br ONO2
SAJC/PRELIM2009/P1/Q27 Which of the following reactions would not produce 1,3-dicarboxylic acid?
CHO
A
CHO
+ Fehling's solution followed by acidification
H C CH2CH3 + hot acidified potassium manganate (VII)
B
COOCH3
CN
C
COOCH3
+ aqueous H2SO4, reflux
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CH(OH)CH3
D
COCH3
+ alkaline aqueous iodine followed by acidification
SAJC/PRELIM2009/P1/Q28 The diagram represents a section of a catalytic converter on the exhaust system of a car. Harmful gases are converted into carbon dioxide, nitrogen and water vapour.
CO Hydrocarbons NOx
CO2 H2O N2 Platinum and Rhodium catalyst
Which statement about the catalytic convertor is not true?
A B C D
NOx are reduced to N2 by the excess CO present. Cars fitted with a catalytic converter may run on leaded petrol. Platinum and rhodium catalyse redox reactions. Platinum and rhodium are coated on a ceramic honeycomb structure so as to maximise surface area.
SAJC/PRELIM2009/P1/Q29 The amino acids lysine and glutamine can react with each other to form peptide linkages.
H H2N C COOH CH2CH2CH2CH2NH2 lysine
H H2N C COOH CH2CH2CONH2 glutamine
What is the maximum number of different compounds, each containing one peptide linkage that can be formed from one molecule of lysine and one molecule of glutamine? A B
2 3
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C D
4 5
SAJC/PRELIM2009/P1/Q30 X possesses a chiral centre and forms a zwitterion. Which one of the following structures could X be?
OH COOH
A
H3C NH2
NH2
B
HOOC
CH2OH CHOH(CH3)
NO2
NH2 CH
D
COOH HO
SRJC/PRELIM2009/P1/Q22
Identify the number of sp2 and sp3 hybridised carbon atoms in the given structure:
H H O C C C H
A B C
sp2 2 3 8
sp3 5 4 5 69
Which of the following is the propagation step in the reaction between ethane and bromine in the presence of ultraviolet light? A B C D Br2 2Br CH3CH2 + Br CH3CH2Br CH3CH2 + HBr CH3CH2Br + H CH3CH2 + Br2 CH3CH2Br + Br
Ethene reacts with bromine to form dibromoethane. Which of the following best describes the organic intermediate in this reaction? A B C D The shape about each carbon in the intermediate is trigonal planar. It has a negative charge. It is an electrophile. It is a free radical.
Which sequence shows the increasing ease of hydrolysis? A B C D C6H5Br > C6H5CH2Cl > CH3CH2COCl > CH3CH2I CH3CH2COCl > CH3CH2I > C6H5CH2Br > C6H5CH2Cl C6H5Cl > CH3COCH2Cl > C6H5CH2Br > CH3CH2I C6H5Br > CH3CH2Cl > C6H5CH2I > CH3CH2COCl
Which reagent could be used to distinguish between pentan-2-ol and pentan-2-one?

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A B C D
aqueous bromine alkaline aqueous iodine acidified potassium manganate(VII) sodium carbonate
A 3-step reaction scheme is shown below.
O CH2Br CH2OH C H H
OH C CN
II
Oxidation
III
CH3
CH3
CH3
CH3
Which one of the following correctly describes the types of organic reactions for steps I and III? Step I A B C D Electrophilic substitution Electrophilic substitution Nucleophilic substitution Nucleophilic substitution Step III Nucleophilic addition Electrophilic addition Nucleophilic addition Electrophilic substitution
An ester G has the following chemical formula: C3H7COOC3H7 Which pair of compounds can be produced when G is refluxed with dilute sulphuric acid? A B C D CH3CH2CH2COOH and (CH3)2CO (CH3)2CHCOOH and CH3CH2CH2OH CH3CH2COOH and CH3CH2CH2OH (CH3)2CHCOCl and (CH3)2CHOH
Partial hydrolysis of insulin, the hormone essential for carbohydrate metabolism gives the following tripeptide.
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CH2CH2CO2H (CH3)2CHCH(NH2)CONHCHCONHCH(CH3)CO2H Insulin Which compound could be obtained by further hydrolysis of this tripeptide? A B C D CH3CH(CO2H)2 (CH3)2CHCH(NH2)CONH2 H2NCONHCH(CH2CH2CO2H)CO2H H2NCH(CH2CH2CO2H)CONHCH(CH3)CO2H
The painkiller Phenacetin can be made as follows:

NH2 NHCOCH3
Reagent J
OCH2CH3
OCH2CH3
Phenacetin What could be the reagent J? A B C D CH3CH2NH2 CH3COCH3 CH3COOH CH3COCl
TPJC/PRELIM2009/P1/Q18
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73
74
75
76
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VJC/PRELIM2009/P1/Q19
The hydride ion, H-, is a strong reducing agent, a good nucleophile and a good base. Which one of the following conversions would the hydride ion not be expected to bring about? A B C D C2H5Br to C2H6 CH3CH3 to CH2=CH2 CH3CHO to CH3CH2OH CH3CO2H to CH3CO2-
2,2-dimethylpropane reacts with chlorine gas in the presence of ultraviolet light to give a mixture of products. Which one of the following statements is correct regarding this reaction? A B C D Only one mono-substituted product is formed. Only the propagation step involves C-Cl bond formation. Only the initiation step of the mechanism involves homolytic fission. Both propagation and termination steps produce hydrogen chloride.
Which one of the following cannot be made directly from methylbenzene? A B C D
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Nootkatone is one of the organic compounds found in grapefruit. Its structure is as shown below.
Which statement is correct about nootkatone? A B C D It forms a pale yellow precipitate with alkaline I2(aq). It reacts with Tollens reagent to give a silver mirror. It reacts with potassium cyanide in ethanol to form a nitrile compound. It reacts with hot acidified potassium manganate(VII) to form one organic product.
An organic compound X undergoes the following reactions: (i) (ii) (iii) It decolourises a solution of bromine in tetrachloromethane. It reacts with phosphorus pentachloride giving copious white fumes of HCl. It reacts with hot alkali to give a compound with two alcohol functional groups.
Which compound could be X? A B C D HOH2CCH=CHCH=CHCH2Cl Cl2CHCH=CHCH2COOH BrCH2CH2CHClCH2COCl ClCH2CH2CH=CHCH(Cl)CH2OH
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Which process will not give a good yield of CH3CO(CH2)3CO2H?
CH3 Cl
A
KOH in ethanol heat
Hot KMnO4(aq), H3O+
KOH(aq) H2NCO(CH2)3CHClCH3
B C
Hot KMnO4(aq), H3O+
heat
NaOH(alcohol) CH3CH(OH)(CH2)3CH2Cl
CH3
Hot KMnO4(aq), H3O+
Heat
Hot KMnO4(aq), H3O+
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The pinacol rearrangement involves the reaction of a diol in acidic conditions to form a carbonyl compound as shown below.
Which one of the following structural formulae is not a product of the pinacol rearrangement of 2,3-diphenylpentane-2,3-diol with the structure as shown below?
OH OH
2,3-diphenylpentane-2,3-diol
O
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Compound X is boiled under reflux with an excess of aqueous sodium hydroxide.
Compound X What is the main product? A C
An ester Y is boiled with aqueous hydrochloric acid and the resulting mixture is cooled. The final products include a compound C4H8O2 which gives a pale yellow precipitate with alkaline aqueous iodine. Which formula could represent Y? A B C D CH3OCOCH2CH2CH3 C6H5CO2CH2CH2CH2CHO CH3CO2CH2CH2COCH3 C6H5CO2CH(CH3)CH2CH2OH
Tyramine is an alkaloid found, among other places, in mistletoe and ripe cheese.
HO NH2
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Tyramine How many moles of ethanoyl chloride react completely with one mole of tyramine? A 0 B 1 C 2 D 3
Which sequence correctly shows the compounds, in aqueous solutions of equal concentration, in order of increasing pH? A B C D C2H5OH < C6H5COCl < CH3CH(NH2)CO2H < CH3CH2NH2 CH3CH2OH < CH3CH2NH3+Cl- < C6H5NH2 < CH3CH2NH2 C6H5OH < C6H5NH2 < CH3CONH2 < CH3CH2NH3+ClCH3COCl < C6H5CO2H < CH3CONH2 < C6H5NH2
A liquid P is sparingly soluble in water but dissolves readily in cold hydrochloric acid. Evaporation of this solution yields a crystalline solid. What is the identity of P? A B C D C6H5NH2 C6H5CH3 CH3(CH2)10CONH2 HO2CCH(CH3)NH2
YJC/PRELIM2009/P1/Q17
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MCQ Section B
ACJC/PRELIM 2009/P1/Q39 1 Which of the following reactions will give identical observation? 1 2 3 Bromine and ethene Bromine and ethane in the presence of uv light Bromine and benzene in the presence of halogen carrier
ACJC/PRELIM 2009/P1/Q40 2 Compound X has molecular formula C3H4O4. It can react with HCl to give C3H3O3Cl. One mole of X reacts with sodium metal to give one mole of H2 gas.
Which of the following can be X? 1 2 3 CH2(OH)COCOOH CHOCH(OH)COOH CH2(COOH)2
AJC/PRELIM 2009/P1/Q37 37 Dopamine is a neurotransmitter found in many animals, including vertebrates and invertebrates. Which of the following statements are correct?
CO2H HO HO CH2CH NH2

dopamine 1 2 3 1 mole of dopamine reacts with 3 moles of acyl chloride 1 mole of dopamine reacts with 1 mole of HBr. 1 mole of dopamine reacts with 3 moles of Na2CO3
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37
Ethyl propanoate, CH3CH2OCOCH2CH3 undergoes acidic hydrolysis in the presence of H218O. Which of the following products are formed? CH3CH218OH 1 2 3 CH3CH2CO18OH CH3CH2OH
38
Which of the following molecules are planar? 1

CHO
2
O2N
H C
H C CN
39
In which sequence are the compounds listed in order of increasing ease of hydrolysis? 1 2 3 C6H5Cl, CH3CH2Cl, CH3COCl CH3CH2I, CH3CH2Br, CH3CH2Cl C6H5Cl, CH3Cl, CH3CH2Cl
40
The molecule of benzene, C6H6 is a regular hexagon in which the electrons are described as delocalised. Which of the following statements support this structure? 1 2 It prevents benzene from undergoing addition reactions. All CC bonds lengths in benzene are intermediate between CC bond in an alkane and C=C bond in an alkene.
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The enthalpy change of hydrogenation of benzene is less exothermic than that predicted for cyclohexatriene.
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CJC/PRELIM 2009/P1/Q36 36
CH=CH2 CHBrCH3 COOH COOH
step 1 I
CH3 CH3
step 2
II
step 3 III
COOH O2N COOH
step IV 4
COOH
H2N
COOH
Which type of reaction has taken place in the above reaction scheme? 1 2 3 electrophilic substitution oxidation reduction
CJC/PRELIM 2009/P1/Q37 37 Chloroethane can be formed from bromoethane in two steps.

Step 1 Step 2
CH3CH2Br
CH3CH2OH
CH3CH2Cl
Which statements about these steps are correct? 1 2 3 Step 1 involves a nucleophilic substitution. Hot aqueous sodium hydroxide is the reagent in step 1. Hot aqueous sodium chloride is the reagent in step 2.
CJC/PRELIM 2009/P1/Q38 38 Benzoylglycine (hippuric acid) was first isolated from stallions urine.
CONHCH2CO2H
Which properties does this compound possess? 1 2 3 It can be hydrolysed to produce an amino acid. It can be made by reacting benzoyl chloride, C6H5COCl with aminoethanoic acid, NH2CH2CO2H. It can be neutralised by reaction with cold aqueous sodium hydroxide.
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CJC/PRELIM 2009/P1/Q39 39 Which of the following compounds form a single organic product when it is heated with acidified potassium manganate(VII) solution? 1 2 3
CH3
CH3CH2CH2CH=CH2
CH 3
CH3
CJC/PRELIM 2009/P1/Q40 40 For the upcoming inaugural Youth Olympics Games (YOG) in Singapore, former Olympic winners will share their experiences with participating athletes in dealing with competition pressures and sport injuries. One common sport injury is muscle sprain. To reduce swelling and pain, ibuprofen is usually administered. The structure of ibuprofen is shown.
CH3 CH3 H3C
CO2H
Which of the following are expected to be true for ibuprofen? 1 On heating with hot acidified KMnO4, the following is formed:
CH3
CO2H HO2C
2 3
It has very low solubility in water. It can be reduced by LiAlH4.
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JJC/PRELIM 2009/P1/Q37 37. Alkanes can be prepared from iodoalkanes by heating under reflux with sodium (in ether) according to the equation: 2RI + 2Na RR + 2NaI Which alkanes will be produced if a mixture containing equal amounts of CH3CH2I (iodoethane) and CH3CHICH3 (2-iodopropane) is used? CH3 1 CH3CHCHCH3 CH3
CH3CH2CHCH3 CH3
CH3CH2CH2CH3
JJC/PRELIM 2009/P1/Q38 38. O 1. CH3CH2MgBr, ether 2. H3O+ OH CH2CH3
Conc. H2SO4, heat
CH2CH3
1. O3 2. Zn, CH3COOH O O
HCCH2CH2CH2CH2CCH2CH3
Based on the information given in the reaction scheme above, which of the following
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reaction is involved?
1 2 3
nucleophilic addition dehydration oxidation
JJC/PRELIM 2009/P1/Q39 39. Serine is an amino acid commonly found in human body. Its structural formula is CH2OHCH(NH2)CO2H. Which of the following statements about serine are correct? 1 2 In a buffer solution of pH 9, serine is attracted towards the anode when a potential difference is applied. In a polypeptide, the hydroxyl group of serine maintains the secondary structure by forming hydrogen bonds with polar R groups of other amino acid residues.
The zwitterionic form of serine is
H + H3NCCOO CH2O
JJC/PRELIM 2009/P1/Q40
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40.
Which statements about methylamine, dimethylamine and trimethylamine are incorrect?
Compound CH3NH2 (CH3)2NH (CH3)3N
pKb 3.36 3.29 4.28
1 2 3
They are trigonal planar with respect to the nitrogen atom. They all form amides with ethanoyl chloride. Trimethylamine is a weaker base than dimethylamine due to the steric hindrance which decreases the chances of protonation.
36
Consider the following reaction scheme involving benzaldehyde and ammonia in methanol to form an imine.
CHO NH
NH3
H2 O
Which of the following statement(s) is/are true? 1 2 3 Ammonia is the nucleophile in this reaction. The rate of backward reaction is increased by the addition of H2O. The yield of imine is increased by the addition of NaOH to the reacting mixture of benzaldehyde and ammonia.
37
When iodoethane is heated to about 100C in a sealed tube with concentrated ammonia solution, the possible product(s) is/are 1 C2H5NH2 97
2 3
(C2H5)2NH (C2H5)3N
38
The compound below is Binapacryl which is often used as a fungicide.

OH O 2N CH3 CH3
NO 2
Which of the following statement(s) is/are true about the fungicide? 1 It undergoes a more vigorous reaction with potassium metal than sodium metal. It reacts with ethanoic acid in the presence of concentrated sulfuric acid to give a pleasant smelling liquid. It cannot exist as a racemic mixture .
3 39
Vitamin B5 has the following structure.

OH NH HO H3C CH3 O OH O
Which of the following statement(s) correctly describe the chemistry of Vitamin B5? 1 2 3 Vitamin B5 reacts with 3 moles of PCl5. The carboxylic acid group reacts with CH3NH2 to form an amide. Vitamin B5 reacts with 2 moles of HCN.
40
Psilocin is a psychedelic mushroom alkaloid. It is the active compound that produces hallucinations from ingesting magic mushrooms and amplifies sensory experience. Compound Y is a derivative of Psilocin. 98
NH OH CH3
N H
Y
Which of the following statement(s) is/are true about Y? 1 2 3 It gives white fumes with CH3COCl. It dissolves in both aqueous acids and alkalis. The nitrogen-containing group in the ring has a lower pKb than the nitrogen-containing group in the side chain.
37
In which of the following reactions is the reactive carbon tetrahedral in the organic intermediate? 1 2 3
CH4 + Cl2
uv
CH3Cl + HCl
HCHO + HCN
trace KCN
CH2(OH)CN
Cl + HCl
+ Cl2
AlCl3
38
Which statements about the complete combustion of an alkene, CnH2n, in oxygen are correct? 1 2 3 The volume of oxygen required is directly proportional to the number of carbon atoms present in the molecule. The volume of gas produced at 25 C is the same as for the complete combustion of an alkane with the same number of carbon atoms per molecule. At 120 C, the volume of steam produced is always twice the volume of carbon dioxide. 99
39
Compound F is used to treat urinary incontinence. The structure of F is shown below.

O HO CH3 H3C CH3 N H OH O OH
F Which of the following statements about the reactions of F are incorrect? 1 2 3 40 1 mol of F reacts with SOCl2 to release 3 mol of HCl gas. 1 mol of F reacts with Na metal to release 3 mol of H2 gas. 1 mol of F reacts with Na2CO3 to release 2 mol of CO2 gas.
Which sequence shows the nitrogen compounds in increasing order of pKb value? 1 2 3 CH3CH2NHCH3, C6H5CH2NH2, CH3CONH2 C6H5NH2, NH3, CH3NH2 CH3CH2N(CH3)2, C6H5NH2, CH3CH2NHCH3
MI/PRELIM 2009/P1/Q37 Reactants that form an organic product which has an asymmetric carbon atom include 1 2 3 but-2-ene and HBr propanal and HCN propanone and NaBH4
MI/PRELIM 2009/P1/Q38 A car burning lead-free fuel has a catalytic converter fitted to its exhaust. On analysis, its exhaust gases are shown to contain small quantities of nitrogen oxides. Which modifications would result in lower exhaust concentrations of nitrogen oxides? 1 2 3 an increase in the surface area of the catalyst in the converter. an increase in the rate of flow of the exhaust gases through the converter. a much higher temperature of combustion in the engine.
MI/PRELIM 2009/P1/Q39 The drug tamoxifen, which is used in the treatment of cancer, has the structure
100
Which of the following statement(s) about tamoxifen is/are correct? 1 2 3 it is insoluble in HCl(aq). it has a stereoisomer. it can undergo free radical substitution with chlorine.
MI/PRELIM 2009/P1/Q40 Which of the following correctly list(s) the compounds in order of decreasing acidity?
CH3
Cl
1
OH
,
OH OH
,
OH
NO2
CH3

OH
,
OH OH
,
OH
101
CONH2 CH2OH NH2
3
,
OH
OH
NJC/PRELIM2009/P1/Q37 Samples of the gases CH3Cl and Cl2 are mixed together and irradiated with light. Which statements are true? 1 2 3 Chlorine atoms are formed in the initiation step. The chlorine radical acts as a catalyst in the propagation steps. Ethane is produced in trace amounts in the termination step.
NJC/PRELIM2009/P1/Q38 Which reagents can be used to distinguish between these two compounds?
CH3 H HO C C CH3 H CHO H C C O CH2 Br O
1 2
Fehlings solution Silver nitrate solution
102
Alkaline iodine solution
NJC/PRELIM2009/P1/Q39 Which reactions yield a carbon compound incorporating deuterium, D? [D =2H] 1 CH3COCH3 CH3CO2CH3 CH3CH2CN NaOD, I2 D2O NaOD D2O NaOD D2O
NJC/PRELIM2009/P1/Q40 Nylon is a biodegradable polymer used in clothes manufacturing. A section of the nylon molecule shown below: ( NH(CH2)5CO )n Which statement about nylon is true? 1 2 3 It contains amide linkages. It is basic. It gives an orange precipitate with 2,4-dinitrophenylhydrazine.
Pentaerythritol is an intermediate in the manufacture of paint.

HO CH2 C HO CH2 CH2 OH CH2 OH
pentaerythritol Which of the following statements about pentaerythritol are correct? 1 It decolourises acidified potassium manganate(VII) on warming 103
2 3
It reacts with metallic sodium It is formed via the reaction of 1,4-pentadiene,

H2C CH CH2 CH CH2
with cold dilute potassium manganate (VII)

Which of the following statements is true of the nitration of benzene? 1 2 3 Concentrated H2SO4 acts as an acid to generate the NO2 ion Concentrated H2SO4 acts as a catalyst The organic intermediate has five carbon atoms which are sp hybridised
2 +
Which of the following statement(s) is/are true for both methylbenzene and phenol? 1 2 3 Both can react with nitric acid via the same mechanism Both reacts with aqueous bromine at room temperature to form at white precipitate Both reacts with hot acidified KMnO4 to form the same organic product
Capsaicin, the active component of chilli peppers, has the following structure:
HO H H3 C O N CH3 O CH3
capsaicin Which of the following statements about capsaicin are correct?

104
1 2 3
It contains a total of nine sp hybridised carbon atoms It reacts with dilute hydrochloric acid under room temperature It has only one chiral centre
105
106
107
108
SAJC/PRELIM2009/P1/Q37 Thyroxine and Cyproterone are compounds that are often used in hormone therapy.
I HO I O I Thyroxine I H CH2 C NH2 COOH O Cyproterone CH3 Cl COCH3 OH CH3
Which of the following reagents could be used to distinguish between the two compounds? 1 2 3 Neutral FeCl3 Alkaline aqueous iodine Sodium carbonate
SAJC/PRELIM2009/P1/Q38 Which of the following properties of benzene may be directly attributed to the stability associated with the delocalised electrons? 1 2 3 Its susceptibility to attack by nucleophilic reagents. Its tendency to undergo substitution rather than addition reactions. The carbon-carbon bond lengths are between those of C-C bonds and C=C bonds. SAJC/PRELIM2009/P1/Q39 By varying the conditions of the reaction between propan-1-ol and concentrated sulfuric acid, which of the following compounds can be obtained? 1 2 3 CH3CH=CH2 CH3CH2CH2OCH2CH2CH3 CH3CH2CH2OSO3H
109
SAJC/PRELIM2009/P1/Q40 Compound Q, with molecular formula C6H12, was reacted with acidified potassium manganate(VII) and the resultant mixture obtained was colourless. The mixture was thereafter distilled to form distillate R and residual solution S.
Distillate R is able to form a yellow precipitate with alkaline aqueous iodine. Residual solution S reacts with sodium carbonate to form a colourless gas.
Which of the following statements are true? 1 2 3 Compound Q will decolourise aqueous bromine Distillate R can form an orange precipitate with 2,4-dinitrophenylhydrazine Residual solution S can form white fumes with PCl5.
Which of the following compound(s) forms a yellow precipitate when warmed with alkaline aqueous iodine? 1 2 3 butan-2-ol 1-phenylethanol 2-phenylethanol
Which of the following reagents can be used to distinguish between C6H5CHO and C6H5COCH3? 1 2 3 Aqueous [Ag(NH3)2]+ Alkaline solution of iodine 2,4-dinitrophenylhydrazine
It has been noted that prolonged exposure of wine to the atmosphere will result in the wine becoming vinegary. Therefore, wineries attempt to prevent such exposure by storing the wine in a mixture of carbon dioxide and nitrogen. How does this mixture prevent the vinegary taste from occurring? 1 Oxidation of ethanol into ethanoic acid will be prevented. 2 The acidity of the wine will be decreased. 3 The amount of carbon dioxide dissolved in the wine will be increased. 110
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 H CH2 CH2 N CH3 N H Compound K
Which of the following statement(s) is/are true for compound K? 1 2 3 It gives white fumes with CH3COCl. It dissolves in both aqueous acids and alkalis. The nitrogen containing group in the ring has a lower pKb than the nitrogen containing group in the side chain.
111
112
Compound X changes the colour of dichromate(VI) from orange to green. Which of the following can be compound X? 1 2 3 C6H5CH2CHO C6H5CH(OH)CH3 C6H5CO2CH2CH3
excess hot acidified
potassium
The cholesterol-lowering agents called statins, such as pravastatin, are among the most widely prescribed drugs in the world.
113
Which statements about pravastatin are correct?
1 2
The pravastatin molecule has 8 chiral centres. When treated with an excess of hot concentrated acidified KMnO 4, pravastatin will produce a compound with which gives an orange precipitate with 2,4-dinitrophenylhydrazine. When 1 mole of pravastatin is treated with an excess of sodium, 2 moles of hydrogen is produced.
GABA is a neurotransmitter released by red algae which encourages shellfish larvae to settle on the ocean bed. H2NCH2CH2CH2CO2H GABA Which statements about GABA are correct? 1 2 3 It is a 2-aminocarboxylic acid. It is soluble in water due to zwitterion formation. It migrates to the anode of an electrolytic cell at pH 12.
114
115
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2012 JC 2 H2 Chemistry Revision Topic 10: Organic Chemistry

SAJC Chemistry Unit 2009

Which of the following is a possible hydrolysis product of CS? A

SAJC Chemistry Unit 2009

Which of the following could be product E? A

SAJC Chemistry Unit 2009

ACJC/PRELIM 2009/P1/Q28 6 Phenol reacts with diazonium chloride as shown.

SAJC Chemistry Unit 2009

How many chiral carbon atoms are present in this molecule? A 4 B 5 C 6 D 7

SAJC Chemistry Unit 2009

SAJC Chemistry Unit 2009

SAJC Chemistry Unit 2009

SAJC Chemistry Unit 2009

SAJC Chemistry Unit 2009

I2 in NaOH (aq) PCl5

Cu2+ in alkaline solution acidified potassium dichromate

SAJC Chemistry Unit 2009

SAJC Chemistry Unit 2009

SAJC Chemistry Unit 2009

Which compound can be synthesized from prop-1-ene in less than 3 steps? A

SAJC Chemistry Unit 2009

A mixture of amino acids can be separated by electrophoresis.

Mixture of filter paper amino acids

SAJC Chemistry Unit 2009

SAJC Chemistry Unit 2009

SAJC Chemistry Unit 2009

glucose How many stereoisomers does glucose exhibit? A 21 B 22 C 23 D 24

SAJC Chemistry Unit 2009

SAJC Chemistry Unit 2009

SAJC Chemistry Unit 2009

A 2,4-DNPH B Na metal C SOCl2 D Br2(aq)

SAJC Chemistry Unit 2009

CO2CH3 OCOCH3 NaOH(aq)

CO2Na OCOCH3 HCl(aq)

conc H2SO4 reflux

SAJC Chemistry Unit 2009

SAJC Chemistry Unit 2009

SAJC Chemistry Unit 2009

JJC/PRELIM 2009/P1/Q20 20. The structure of compound X is given below.

What is the intermediate formed in this reaction?

SAJC Chemistry Unit 2009

Mass / g 0 0.15 1.05

SAJC Chemistry Unit 2009

CH3(CH2)2CH=CHCO2H CH3(CH2)4CH2COCH2CH3 CH3(CH2)4CO2CH2CH3 CH3CH2CO2(CH2)4CH3

Which statement about tetracycline is correct?

JJC/PRELIM 2009/P1/Q27 27. A nitrile X undergoes the following two reactions:

Nitrile X reduction acid hydrolysis

SAJC Chemistry Unit 2009

SAJC Chemistry Unit 2009

Compound P is optically active.

How many chiral centre(s) does compound P have? A B C D 1 2 3 4

SAJC Chemistry Unit 2009

A student attempts to synthesise compound S from the following synthetic route.

1. Br2/H2O 2. KCN, base

Which of the following could be compound S that is formed in this reaction?

SAJC Chemistry Unit 2009

C2H5OH CH3CH(OH)C2H5 C6H5CH(OH)C2H5

SAJC Chemistry Unit 2009

Which of the following could be compound Q? A

SAJC Chemistry Unit 2009

Spironolactone is an anti-androgen used as a common component in hormone therapy.

SAJC Chemistry Unit 2009