Organic MCQ 2010 ANS Updated 22-05-2013

Topic 10: Organic Chemistry
MCQ Section A
ACJC/PRELIM 2010/P1/Q21
After heating acidified potassium permanganate with the molecule below, how
many sp2 carbons are there present in the resultant compound?
CH3
HO
OH
10
11
OH
O
Cl
OH
OH
How many stereoisomers are there in the
compound shown?
When excess BrCl is added to the methylbenzene in the presence of UV light,
which organic compound will be produced in the smallest proportion?
CH 2Br
CH 2Cl
CHBr 2
CH 2
CH 2
When the following compound shown below is oxidized with alkaline potassium
manganate(VII), one of the products include
CH2
ClHClCH
2CH 22C
CH3CO
H2
ANS: C
Which one of the following alcohols will give the largest number of alkenes when
treated with concentrated sulphuric acid?
A
A 1,2-hydride shift is common in producing a more stable carbocation.
For example, when removing the halogen from CH 3CH2CH2Cl, a hydride shift will
take place to produce a more stable carbocation.
H
H y d rid e s h ift
H
+
What will be the most likely product formed when (CH 3)2CHCHClCH3 is added to
AlCl3 and then the mixture is added to benzene?
(Ph represents benzene)
A
CH3CH2CH2CH2CH2Ph
(CH3)2CHCH(Ph)CH3
(CH3)2CHCH2CH2Ph
(CH3)2C(Ph)CH2CH3
Ethanal reacts with CN from HCN in the presence of a weak base as shown below
OH
O
CH 3
CH 3
HCN
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
(CH3)2C(CHO)CH2OH
(CH3)2C(OH)CH2CHO
(CH3)2C(OH)COCH3
Phenol has a pKa of 5.7. Which one of the following has a lower pKa value?
A (CH3)3CCOOH
2,4,6-trimethylphenol
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
C6H5NH2
C6H5CN
C6H5OH
Acetaminophen is a drug used in headache remedies. It has the structure
HO
CH3
Which of the following equations gives the best method for its synthesis?
H CH3
CH3
Cl
HO
N C O
A HO
H NC
O
HCl
HO
C HO
NH2
NHCOCl
D HO
NHNH 2
HO
CH 3COCl
CH 3Cl
HO
CH3
CH3
HO
CH 3CHO
CH3
HCl
Cl 2
NH 3
AJC/PRELIM 2010/P1/Q21
In recent years, a number of athletes have been banned from sports because of their
illegal use of synthetic testosterone.
CH3 OH
CH3
O
testosterone
Testosterone is first refluxed with concentrated KMnO 4, 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
Use of the Data Booklet is relevant to this question.
The bond energy of the CH bond (438 kJ mol 1) 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 CH 4 and the
halogen is incorrect?
A
Bromine and iodine essentially do not react with methane.
Fluorine is so reactive that neither UV light or heat is needed.
The order of halogen reactivity is due to the decreasing strength of the HX bond.
The H for the first propagation step is more endothermic for the chlorination of C 2H6.
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
NO2
deuteriobenzene
16%
20%
3-nitrodeuteriobenzene
33%
45%
Four drops of 1chlorobutane, 1bromobutane, 1iodobutane were put separately into
three testtubes containing 1.0 cm 3 of aqueous silver nitrate at 60 C.
A hydrolysis reaction occurred. (R represents the butane chain C 4H9 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.
The ionisation energy of the halogen decreases from Cl to I.
The RX bond polarity decreases from RCl to RI.
The solubility of AgX(s) decreases from AgCl to AgI.
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
CH3CO2H
K2Cr2O7
PCl5
The compound T, CH3COCH2CHO, was reacted in separate experiments with:
alkaline aqueous iodine;
2,4dinitrophenylhydrazine;
Tollens reagent [Ag(NH3)2]+(aq);
lithium aluminium hydride in dry ether.
One mole of T could
A
form two moles of CHI3 in (i).
react with two moles of 2,4dinitrophenylhydrazine in (ii).
form one mole of CH3COCH2CH2OH and two moles of Ag in (iii).
form a product in (iv) which further reacts with Na to produce two moles of H 2 gas.
Which of the following steps take place in the reaction between the pairs of reagents?
reagents
step
CH3
ethanoyl chloride and water
Cl
O
H
O2N
CH3CH2
propanal and 2,4DNPH
C
H
N NH
H
NO2
H3C
H
C
propene and bromine

monochloride
Cl
Br
CH3
methylbenzene and nitric acid
NO2+
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?
CH3CO2
CO2H
H2NCH
CH2CO2H
CH2CH2NH2
NH2
CH2CHNHCOCH
CO2
CH2CO2
Dopamine is a drug used in the treatment of Parkinsons disease.
HO
CH2CH2NH2
HO
Which of the following statements about this compound is correct?

A
It can dissolve in aqueous sodium hydroxide but not hydrochloric acid.
It can be synthesised
from
HO
CH2I
HO
It decolourises aqueous bromine only in the presence of light.
Three moles of CH3COOH will react with one mole of Dopamine.
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
LysLeuSerTyrLeuAlaPheGln
LeuSerTyrLeuAlaPheGlnLys
CJC/PRELIM 2010/P1/Q20
In what way is propene similar to propane?
A
B
C
D
Both can be obtained by the dehydration of alcohols.

Both can react with chlorine under suitable conditions.
Both can be hydrogenated using a suitable catalyst.
Both can undergo polymerisation under suitable conditions.
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
CH3CH2CH2CH2Cl
and CH3CH2CCl2CH3
C
D
CH3CHClCHClCH3 and ClCH2CH2CH2CH2Cl

CH3CH2CH2CH2Cl
and CH3CH2CH2CHCl2
and ClCH2CH2CH2CH2Cl
The following shows the time taken for appearance of precipitate after adding aqueous
AgNO3 to four halogen derivatives separately.
Halogen Derivative
Chlorobenzene
2-chlorobutane
2-bromobutane
2-iodobutane
Time for precipitate to appear

No precipitate
10 minutes
2 minutes
Instantaneous
Which of the following would be the best explanation for the observation?
A
B
C
D
The lattice energy becomes more exothermic from AgCl to AgI.

The ease of electron cloud distortion decreases from chlorobenzene to
2-iodobutane.
The carbon-halogen bond strength decreases from chlorobenzene to 2iodobutane.
The carbon-halogen bond length decreases from 2-chlorobutane to 2iodobutane.
Tyrosol is a naturally occurring oxidant found in olive oil.
HO
OH
Tyrosol
Which statement about Tyrosol is incorrect?
A
B
C
1 mol of Tyrosol will react with 2 mol of Na to give 1 mol of H 2.

1 mol of Tyrosol will react with 2 mol of PCl5 to give 2 mol of HCl.
Tyrosol will react with acidified KMnO4 under reflux to give a carboxylic
acid.
Tyrosol will react with H2SO4 under suitable conditions to give an alkene.
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
OH
OH
OH
Catechin
O
ring is not involved in any of the following reactions.

Which statement about catechin is correct?
A
B
C
D
It can undergo oxidation with hot acidified K 2Cr2O7.

It can undergo electrophilic addition with Br 2(aq).
1 mol of catechin can react with 5 mol of NaOH.
1 mol of catechin can react with 4 mol of Na2CO3.
In which reaction does the organic reactant have a bond angle that is larger than the
carbon-containing product?
A
B
C
D
complete combustion of ethene in air

heating methanal with LiAlH4 in dry ether
mixing methane with chlorine gas in the presence of UV light
heating bromoethane under reflux with alcoholic potassium hydroxide
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.
Compound X undergoes oxidative cleavage with hot acidified KMnO 4 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?
A
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?

A
B
C
D
It is an sp2-sp2 overlap.
Formamide is a weaker base than methylamine.
The electrons in the filled p orbitals on C and N of methylamine repel each
other.
The electron withdrawing C=O group in formamide draws the lone pair of
electrons on N closer to itself.
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
B
C
D
When treated with NaBH4 in the presence of methanol, it forms a compound

containing 5 hydroxy groups.
When warmed with aqueous alkaline iodine, a yellow precipitate is observed.
When treated with cold dilute KMnO4, it forms a compound containing 2
hydroxy groups.
When treated with an excess of hot concentrated acidified KMnO 4, it forms a
compound containing 7 chiral centres.
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
aqueous sodium hydroxide
aqueous bromine
hot acidified potassium manganate(VII)
DHS/PRELIM 2010/P1/Q20
A compound used as optical brightener in detergents has the following
formula.
CN
CH
CH
CH
CH
NC
Which of the following is likely to be a property of this compound?

A
It is readily soluble in water.
The molecules exist as cistrans isomers.
It is hydrolysed by hot dilute sulfuric acid to give an amine.
It requires 4 mol of hydrogen gas for reduction.
A compound X exhibits structural isomerism, the isomers being members
of different homologous series.
To which pair of isomers could X belong?
A
acyl chlorides and carboxylic acids
carboxylic acids and esters
amino acids and ammonium salts
amides and amino acids
Hydrobromic acid reacts with ethene to form bromoethane. Which of the
following is the best description of the organic intermediate?
A
It contains carbon, hydrogen and bromine.
It is a free radical.
It is an electrophile.
Its structure is planar.
The first stage of the cumene process for the industrial production of phenol
is as follows.
H3C
H 2S O
CH 3CH=CH 2
CH
CH3
Which one of the following would be the product of reaction, under similar
conditions, between benzene and cyclohexene?
A
CH 2(CH 2)4CH 3
CH=CH(CH 2)3CH 3
Morphine is a narcotic pain reliever used to treat moderate to severe pain.
CH3
N
HO
OH
morphine
Which of the following statements regarding the reaction of morphine with chlorine in
the presence of iron(III) chloride is correct?
CH3
N
The product formed

is
Cl
HO
OH
CH3
N
The product formed

is
Cl
OH
CH3
N
Cl
The product formed

is
Cl
Cl
HO
OH
The product formed is a violet complex.
Deuterium, D, is a heavy isotope of hydrogen. Deuteriobenzene is reacted with a
mixture of nitric acid and sulfuric acid under suitable conditions such that only
monosubstitution takes place.
Assuming that the carbondeuterium bond is broken as easily as a carbon
hydrogen bond, which proportion of the nitrated products will be 4
nitrodeuteriobenzene?
17 %
20 %
33 %
45 %
How many alkenes (including stereoisomers) can be obtained when 2
methylpentan3ol undergoes dehydration?
A
2,4D and MCPA are two common selective weed killers.
Which one of the following reagents can be used to distinguish between

them?
A
sodium metal
phosphorus pentachloride
hot concentrated potassium manganate(VII)
hot acidified potassium dichromate
The reduction of a nitrile produced a compound of formula C 3H7NH2. Which
one of the following compounds would be produced if the same nitrile is
hydrolysed by heating with diluted hydrochloric acid?
A
CH3CONH2
CH3CH2CO2H
(CH3)2CHCO2H
CH3CH2CH2COOH
The Gabriel synthesis shown below gives a high yield of primary amines.
Step I
Step II
The type of reaction taking place in each of the steps is
A
B
C
D
Step I
nucleophilic
substitution
electrophilic
substitution
nucleophilic
substitution
electrophilic
substitution
Step II
hydrolysis
hydrolysis
oxidation
oxidation
Which reaction yields a carbon compound incorporating deuterium, D? [D =
A
2
1
H
]
NaOD
CH3CH2CN
D2O
CH3COOCH3
CH3CN
(CH3)3COH
D2
Ni, heat
D2SO4
H2O, heat
Energy
2 X
HCI/PRELIM 2010/P1/Q19
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
CH3
HO
Compound A
OH
How many possible isomers, including stereoisomers, can be obtained when A is heated
with excess concentrated sulfuric acid?
A 26
B
27
C
28
D
29
Benzene undergoes Friedel-Crafts acylation with ethanoyl chloride to form phenyl
ethanoate, which can be represented as follow:
O
C
CH3
CH3COCl
AlCl3
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.
An alkane E with the molecular formula C 4H10 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
CH3CH(CH3)CH2Cl
Saccharin was an artificial sweetener used in some soft drinks. It was manufactured
from methylbenzene by a series of reactions.
CH3
CH3
CH3
C
ClSO3H
I
SO2Cl
NH3
SO2NH2
II
Which of the following shows the correct reaction type for steps I and II?
I
II
SO2
A
B
C
D
electrophilic substitution
nucleophilic substitution
electrophilic addition
nucleophilic addition
Which sequence shows the compounds in order of decreasing pKa values?
A
B
C
D
CH3CO2H > CF3CO2H > C2H5OH > C6H5OH

CF3CO2H > CH3CO2H > C6H5OH > C2H5OH
C2H5OH > C6H5OH > CH3CO2H > CF3CO2H
C6H5OH > C2H5OH > CH3CO2H > CF3CO2H
The following compound is tested with two reagents separately.
OH
O
C
H
C
O
CH3
What are the expected observations?

Warm with Fehlings reagent
Warm with Tollens reagent
Brick-red precipitate
Silver mirror
No precipitate
Silver mirror
Brick-red precipitate
No silver mirror
No precipitate
No silver mirror
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
Paracetamol is a common analgesic used in the treatment of fever and headaches.
H
N
CH3
C
O
HO
paracetamol
Which deduction about paracetamol can be made from this structure?

A
B
C
D
It is a planar molecule.
It contains an amine group.
It reacts with sodium metal.
It gives an orange precipitate with 2,4-dinitrophenylhydrazine.
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
C6H5Br
CH3CH(Br)CH3
CH3CH2CH2Br
CH3CH(Br)CH3
A
B
C
D
Q
C6H5CN
CH3CH(CN)CH3
CH3CH2CN
CH3CH2CN
The reaction scheme below shows the synthesis of compound S.
Cl
CH3
Br
NaOH(aq)
K2Cr2O7/H2SO4(aq)
heat
heat
Which of the following can be S?

Cl
OH
CH3
CH3
OH
Cl
O
CH3
OH
C
HO
OH
OH
OH
C
O
Compound Y has the following properties:
(i)
it does not decolourise aqueous bromine;
(ii)
it produces an effervescence when reacted with Na2CO3(aq) and
(iii)
it decolourises hot acidified KMnO4(aq).
Which of the following can be Y?
CH3
CH3
OH
CH3
CH2
CH2OH
B
CO2H
CO2H
CH2Br
OH
CH2OH
CH3
CH2CO2H
CH3
NH2
The Diels-Alder reaction is an organic reaction between a conjugated diene and a
substituted alkene to form a substituted cyclohexene system. One such reaction between
buta-1,3-diene and but-3-en-2-one is shown below.
What would be the product formed when the following diene and substituted alkene reacts
in a 1:1 ratio?
IJC/PRELIM 2010/P1/Q5
Which of the following molecules does not exist?
H
Cl
A
C
H
Al
N
O
H
H
Cl
Cl
D
N
OH2
H2O
Cu
H2O
OH
A student carried out an experiment in the following steps.

1
Add aqueous bromine to a solution containing an excess of
sodium iodide.
A
B
C
D
Resulting mixture is shaken with an equal volume of an organic

solvent.
3
Aqueous layer is then separated out and aqueous silver nitrate is
added to it.
4
Mixture is filtered.
5
Concentrated aqueous ammonia is then added to the residue.
6
Resulting mixture is again filtered.
Which of the following will not be observed as the student carries out the steps above?
In step 1, the solution turned brown.
In step 2, a violet organic layer was obtained.
In step 3, a mixture of cream and white precipitate is obtained.
In step 6, yellow precipitate was obtained as the residue after filtration.
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
chavicol
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
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?
CH3
H3C
N N C
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
The antibiotic chlortetracycline is commonly used to treat conjunctivitis in cats. It has the
formula shown.
OH
OH
OH
OH
H2N
O
H
N
HO
How many stereoisomers are possible for chlortetracycline?

A
24
C
26
B
25
D
27
Cl
What is the number of sp2 and sp3 carbon atoms in the structure given below?
sp2
7
1
4
3
A
B
C
D
CH3
sp3
3
3
6
7
A new industrial preparation of ethyl ethanoate has been developed using cheap
sources of ethanol.
Cu catalyst
Cu catalyst
CH3CH2OH
CH3CHO
- H2
+ CH3CH2OH
CH3CH(OH)OCH2CH3
Cu catalyst
- H2
CH3CO2CH2CH3
Which process is involved at some stage in this reaction sequence?

A
disproportionation
B
C
D
Reduction
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
C2H4 + H2O
CH3CH2OH + CH3COOH
conc. H2SO4
C2H4 + H2SO4
CH3CO2CH2CH3 + H2O
OSO3H
D
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
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
CHFClCFCl
CHClCF2Cl
CFClCF2Cl
When ethene reacts with HBr in the presence of aqueous NaNO 3, what are the two
possible products formed?
H
H
H
H
A
H
Br
Br
and
Br
OH
B
H
C
H
D
H
Br
Br
ONO2
Br
OH
Br
OH
ONO2
and
and
and
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
H
H
A
C
H
COOH
CH(CH3)2
COOH
CH2SH
B
H
D
COOH
CH2COOH
COOH
The psychoactive drug in cannabis has the following structure.

HO
H3C
CH2
OH
H3C
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.
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?
A
C
MJC/PRELIM 2010/P1/Q20
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?
A
B
C
D
1-chloro-2,2dimethylbutane
3
3
9
9
3
2
2
2
3
3
3
2
A nitrile Q is treated with LiAlH4 to give a compound of the formula C 2H7N. 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
B
C
D
CH3CONHCH2CH3
CH3CH2CONHCH2CH3
(CH3CO2)(CH3CH2NH3+)
(CH3CH2CO2)(CH3CH2NH3+)
Which of the following shows a correct mechanistic step in the reaction between the stated
reagents?
Reagents
Step
chloropropane and
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
Which method is able to separate benzene from a mixture of benzene, methylbenzene and
phenol?
shaking the mixture with aqueous Br2
shaking the mixture with hot ethanoic acid and concentrated H2SO4
shaking the mixture with hot concentrated HNO3 and concentrated H2SO4
shaking the mixture with hot acidified KMnO4, followed by excess dilute NaOH
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
B
C
D
Disproportionation
Electrophilic Addition
Nucleophilic Addition
Reduction
Pravastatin is a drug used to lower cholesterol in the blood.
Pravastatin
Which statement about Pravastatin is likely to be correct?
A
B
C
D
It reacts with only 3 moles of phosphorus pentachloride at room temperature and

pressure.
It reacts with only 3 moles of hydrogen gas in the presence of nickel catalyst and heat.
It reacts with acidified potassium manganate(VII) under reflux to form one organic
product.
It reacts with liquid bromine in tetrachloromethane to form a compound with 12 chiral
centres.
Which of the following is arranged in decreasing order of solubility in water?
A
B
C
D
sodium propanoate, propanoic acid, propanol, propanal

sodium propanoate, propanoic acid, propanal, propanol
propanoic acid, propanol, propanal, sodium propanoate
propanal, propanol, propanoic acid, sodium propanoate
What is the correct order of increasing pKa for the following compounds?
Cl
COOCH3
COOH
A
B
C
D
E
E, F, H, G
G, E, F, H
G, F, E, H
H, F, E, G
COOH
COBr
Deuterium, D, is an isotope of hydrogen, 1
H.
Which reaction will not yield a stable organic compound containing deuterium?
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)
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:
thr-phe-leu
cys-glu-val
ser-glu-cys
asp-cys
Digestion using the enzyme O:
val-asp-cys-thr
phe-leu-ser
glu-cys
cys-glu
What is the correct sequence of the polypeptide structure?
A
B
C
D
cys-glu-val-ser-glu-cys-asp-cys-thr-phe-leu
cys-glu-val-asp-cys-thr-phe-leu-ser-glu-cys
glu-cys-glu-val-asp-cys-thr-phe-leu-ser-glu
ser-glu-cys-glu-val-asp-cys-thr-phe-leu-ser
NJC/PRELIM 2010/P1/Q20
OH
Which of the following statements about the molecule shown

below is correct?
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).
OH O
CH3
CCH2OH
O
CH3
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
10
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
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
The reaction of ethanol with sulfuric acid is shown in the scheme below:
CH2=CH2
II
Excess acid, 170 oC
I
Excess water
CH3CH2OH
CH3CH2OSO2O
Conc. H2SO4 H
o
IIIExcess alcohol, 140 C
CH3CH2OCH2CH3
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.
Which of the following cannot be used to distinguish between the following compounds?
O
A
B
Hot acidified K2Cr2O7

Neutral iron(III) chloride
HO
CHO
C
D
Silver diammine complex

2,4-dinitrophenylhydrazine
A student treated benzene in a 3-step reaction to yield Nphenyethanamide,
NHCOCH3
Which of the following gives the correct sequence?
Step 1
Step 2
Step 3
Sn, conc HCl
Propanone
A Ethanolic potassium cyanide
LiAlH4 in dry ether
Ethanoyl chloride
B Conc H2SO4 and conc HNO3
Zn, conc HCl
Ethanoyl chloride
C Conc H2SO4 and conc HNO3
Ethanolic ammonia
Ethanoyl chloride
D Chlorine in presence of FeCl3
Which of the following shows the correct order of increasing base strength?
Weakest base
Strongest base
A
CONH2
NH2
CONH2
NH2
NH2
NH3
NH3
CONH2
NH3
NH2
NH2
NH3
NH2
CONH2
NH2
NH2
CH3
NH2
Which of the following is the least likely reaction of compound X?
Compound X
CH3
CH3
NH2
Br
NH2
2Br2(aq)
2HBr
Br
CH3
CH3
NH2
CH3I
NH
CCl4
CH3
HI
B
CH3
NH2
3[O]
COOH
H2SO4
KMnO4
NH3+
H2O
heat
CH3
NH2
4
Cu2+(aq)
(C6H5)3P=CH2
an ylide
CH3
2+
NH2
Cu
(aq)
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
CO
COOH
O
CO
Which of the followig is not true for benzoic anhydride?

A
It reacts with ethanol.
B
It has little solubility in water.
C
D
It reacts with aqueous sodium hydroxide to give the sodium salt.

It gives an orange solid when reacted with 2,4-dinitrophenylhydrazine.
A carbonyl compound can be converted into an alkene by means of the Wittig reaction
where a phosphorus ylide is involved as follows:
CH3
O
(C6H5)3P=CH2
an ylide
CH3
C
CH3
C
CH3
Which of the following pairs of compounds might you use to prepare the following
alkene?
CH3
(C6H5)3P=CHCH3
O
O
(C6H5)3P=CH2
CH3
(C6H5)3P= CHCH3
CH3
(C6H5)3P=CH2
PJC/PRELIM 2010/P1/Q17
Aqueous chlorine is added to aqueous sodium bromide and the mixture is
shaken with an equal volume of trichloromethane. Which observation would be
made?
A The solution in the test-tube turns purple.
B The solution in the test-tube turns orange.
C A colourless layer forms on top of a purple layer.
D A colourless layer forms on top of an orange layer.
Which of the following is a propagation step in the reaction between propane
and chlorine when they are irradiated with ultraviolet light?
A CH3CH2CH2 + Cl CH3CH2CH2Cl
B CH3CH2CH2Cl + Cl CH3CH2CH2 + Cl2
C CH3CH2CHCl + Cl2 CH3CH2CHCl 2 + Cl
D CH3CH2CH2 + Cl2 CH3CH2CHCl + HCl
Fly paper is used as a non-toxic method of trapping houseflies. To increase its
effectiveness, Muscalure, which is a fly pheromone, is added to the paper
during its manufacture. Muscalure has the following structure.
CH3(CH2)7CH=CH(CH2)12CH3
Which of the following statement about Muscalure is not correct?
A It decolourises aqueous bromine.
B It does not rotate plane polarised light.
C It reacts with HBr(g) to give a chiral product.
D It will turn orange acidified potassium dichromate(VI) green.
3-chlorobenzoic acid can be synthesised from benzene in 3 steps.

COOH
Cl
benzene
3-chlorobenzoic acid
Which of the following is the best method for this synthesis?
Step I
Step II
Step III
A
CH3Cl, FeCl3
MnO4-, H+
Cl2, FeCl3
B
CH3Cl, FeCl3
Cl2, FeCl3
MnO4-, H+
C
Cl2, FeCl3
CH3Cl, FeCl3,
MnO4-, H+
D
Cl2, FeCl3
MnO4-, H+
CH3Cl, FeCl3
The following represent a possible synthesis route from cyclohexene to 1,2dibromohexane.
S te p I
intermediate
S te p I I
Br
Br
cyclohexene
1,2-dibromocyclohexane
Which of the following sets of reagents and conditions will not give a good yield
of 1,2-dibromohexane?
Step I
Step II
A cold KMnO4, NaOH(aq)
concentrated H2SO4, KBr
B cold KMnO4, NaOH(aq)
red P, Br2
C Br2(aq)
red P, Br2
D concentrated H2SO4, KBr
Br2, uv
When 0.04 mol of an organic compound F was burnt in excess oxygen, it produced
0.20 mol of water and 0.20 mol of carbon dioxide. When F was treated with alkaline
aqueous iodine, a yellow precipitate was observed.
Which of the following could be F?
A CH3COCH2CH2CH3
B
(CH3)2C(OH)CH=CH2
C CH3CH(OH)CH2CH2CH3
D
CH3CO2CH2CH2CH3
Ibuprofen is a powerful painkiller.

H
CH3
COOH
CH2
OH
CH3
C
CH3
OH
Ibuprofen
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 109.5 o.
D It will decolourise aqueous bromine to give a white precipitate.
The table shows the results of simple tests on a compound H.
Reagents
Observations
Acidified KMnO4(aq), heat
Purple solution turned colourless.
Effervescence observed.
Fehlings solution
No brick-red precipitate
Tollens reagent
Silver mirror observed
From the results of the tests, what could H be?
A
CHO
CH2OH
CHO
CH=CH2
CH2CHO
COCH3
OH
CH2CH3
Esters can be converted to alcohols using lithium aluminium hydride followed by
the addition of water.
O
C2H5
C2H5
C2H5
OH
H
O
H
+ HO
C2H5
H2O
H
+
Which of the following reaction does not occur in this process?

A condensation
B
C hydrolysis
D
Which sequence shows the correct order of increasing ease of hydrolysis of
the following compounds?
COCl
R
A
B
Cl
S
T<U<S<R
T<S<U<R
Cl
Br
C
D
R<S<U<T
R<U<S<T
Which of the following represents the
of the four acids?
A CCl3CO2H <
CH3CO2H
B CCl3CO2H <
CH3CO2H
C C6H5OH
<
C2H5OH
D C6H5OH
<
C2H5OH
correct sequence of increasing pKa value

<
<
<
<
C6H5OH
C2H5OH
CCl3CO2H
CH3CO2H
<
<
<
<
C2H5OH
C6H5OH
CH3CO2H
CCl3CO2H
When aqueous bromine is added to a solution of phenylamine, the reddish
brown colour of bromine disappears. Which of the following statements is true?
A
B
C
D
The resultant solution is more basic.

Nucleophilic substitution reaction has taken place.
Bromine forms a colourless complex with phenylamine.
Br atom is substituted at the 2, 4 and 6- positions with respect to NH2
group.
Alanine is a naturally occurring amino acid. Which of the following statements
about alanine and 3-aminopropanoic acid is not correct?
O
CH 3
OH
NH2
alanine
A
B
C
D
OH
H2N
O
3-aminopropanoic acid
Alanine and 3-aminopropanoic acid are structural isomers.

Alanine has a higher melting point than 3-aminopropanoic acid.
Both compounds are able to react with ethanoic acid to give amide.
Both compounds in their aqueous solutions are able to act as buffers.
RI/PRELIM 2010/P1/Q19
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
O
Cl
CH3O
O
O
O
N
OH
OCH3
Maytansine
A
10
12
14
How many H atoms are in the same plane as Ha in the following molecule?
Ha
H
C C C
In which of the following pairs does reaction I take place more rapidly than reaction II?
A
CH3CH2CH2Br + CH3S
CH3CH2CH2Br + CH3SH
B
(CH3)3CCl + H2O
(CH3)3CBr + H2O
C
I
II
I
II
(CH3)3COH + HBr
I
(CH3)3CCl (1 mol dm3)

+
CH3CH 2O (1 mol dm3)
II
C6H5Cl + H2O
(CH3)3CCl + H2O
II
CH3CH2CH2SCH3 + HBr
(CH3)3COH + HCl
(CH3)3CCl (1 mol dm3)

+
CH3CH 2O (2 mol dm3)
CH3CH2CH2SCH3 + Br
(CH3)3COCH2CH3 + Cl
(CH3)3COCH2CH3 + Cl
C6H5OH + HCl
(CH3)3COH + HCl
Arrange the following compounds in order of decreasing Kb.
N
H
O
CH3
I
A
B
C N
II
I, IV, III, II
I, III, IV, II
CH3CH2
NH2
NH2
III
IV
C II, IV, III, I

D II, III, IV, I
Which of the following can be used to distinguish between the following two
compounds?
OH
OH
O
O
O
CH2=CH
A
B
C
D
hot acidified K2Cr2O7

hot acidified KMnO4
neutral FeCl3(aq)
Br2(aq)
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
B
C
D
CH3COCH2C(OH)(CH3)CH2CHO
CH3COCH=CHCH(CH3)CO2H
CH3COCH2COCH2CH3
CH3COCH2C6H4CHO
A chloroalkane W with molecular formula of C 5H11Cl 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
B
CH3CHClCH2CH2CH3
CH3CH2CHClCH2CH3
C
D
CH3CH(CH3)CHClCH3
CH3CCl(CH3)CH2CH3
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
B
C
D
The reaction is catalysed by a small amount of base.

The slow step involves the formation of a CC bond.
The Gibbs free energy of the reaction is positive at high temperatures.
The reaction between butanal and hydrogen cyanide is slower than the
reaction between butanone and hydrogen cyanide.
What is the structure of Q in the following reaction scheme?
CH3
CH3
CH3
C
HOCH2CH2
A
Cl
Cl
O
O
C
O
SOCl2
P
COCH3
Cl
KMnO4 /
aq H2SO4
heat
Cl
CH3
Cl
Cl
CH3
CH3
C
CH3
Cl
CH3
CH3
C
CH3
Cl
CH2
Cl
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
11-cis-retinal
opsin
rhodopsin
Which of the following statements is correct?

A
B
C
1 mole of 11-cis-retinal reacts with 5 moles of hydrogen gas.

The reaction between 11-cis-retinal and NH2-opsin is a condensation
reaction.
The reaction of 11-cis-retinal with LiAlH4 produces a product that is
optically active.
The reaction between 11-cis-retinal with hot acidified potassium

manganate(VII) produces a total of five different organic products.
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
H O
H2N C COOH
H3N C C NH C COOCH3
CH2
COO
H O
H2N C C NH C COO
CH2
CH2
COOCH3
H O
H3N C C NH C COO
CH2
CH2
COOCH3
H O
H2N C C NH C COOCH3
CH2
CH2
COO
CH2COOH
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?
CH2
CH2
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
valine
H
H2N C COOH
CH3
CH
CH3
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
glutamic acid and lysine
valine and phenylalanine
serine and lysine
glutamic acid and valine
A
B
C
D
on the inside
valine and phenylalanine
glutamic acid and lysine
valine and glutamic acid
phenylalanine and serine
RV/PRELIM 2010/P1/Q18
Punicalagin is a potent antioxidant found in pomegranates.
How many chiral carbons are there in a molecule of punicalagin?

A
Which of the following is the least likely product formed in the termination step in the
reaction of ethane with chlorine in the presence of uv light?
A
HCl
CH3CH2Cl
CH3CHCl2
CH3CH2CH2CH3
What is the number of isomers of C6H12 obtained when the molecule of
CH3CH2C(CH3)BrC2H5 undergoes dehydrohalogenation (elimination of HBr)?
A
Which of the following shows the correct sequence of compounds arranged in order of
decreasing ease of attack by CN?
A
C6H5COC6H5, CH3CH2COCH3, CH3CHO
HCHO, CHCl2COCH3, CH3COC(CH3)3
CH3CH2COCH2CH3, C6H5CHO, CH3COCH3
CH2FCHO, HCHO, CH3CHO
Aldehydes and ketones are produced industrially by the catalytic oxidation of alkenes.
For example, ethanal is manufactured from ethene as shown.
H2C=CH2 + O2 catalys
CH3CHO
The process is also used industrially with but-2-ene, CH 3CH=CHCH3.

Which compound is obtained from but-2-ene?
A
CH3CH2CHO
CH3COCH2CH3
CH3CH2CH2CHO
(CH3)2CHCHO
What is the type of reaction mechanism for both step 1 and step 2 in the reaction
scheme shown below?
Step 1: NaOH, heat under reflux

Step 2: CH3CH2CH2OH, NaOH, heat
A
bimolecular nucleophilic substitution (SN2)
unimolecular nucleophilic substitution (SN1)
Which of the following compounds is expected to form an aqueous solution with the
highest pH?
A
CH3NH2
(CH3)2NH
C
D
Acidified potassium dichromate(VI) of concentration 1 mol dm3 was added in parts to

three separate test-tubes containing 10 cm3 of 1 mol dm3 of unknown solutions X, Y
and Z respectively. Each mixture was warmed and the observations are recorded
below.
colour observed upon warming when
solution
1st part of 3.3 cm3 of

K2Cr2O7 was added
2nd part of 3.3 cm3 of

K2Cr2O7 was added
orange
orange
green
orange
green
green
Which of the following could be the identities of X, Y and Z?

X
C6H5CH2OH
CH3CH2CH2OH
CH3CH2CH2CHO
CH3CH2CH2CH3
CH3C(OH)CHCH3
CH3CHCHCH2OH
CH3CH2CH2COOH
CH3CH2CH2CHO
CH3CH2COCH3
(CH3)2C(OH)CH2CH3
CH3CH(OH)CH2CH3
CH3CH2CH2OH
Which of the following reagents will give a colourless homogeneous solution when
added to phenol?
A
aqueous bromine
aqueous sodium carbonate
aqueous sodium hydroxide
concentrated nitric acid
Dichlorodifluoromethane, CCl2F2, is widely used in aerosol propellants and as a

refrigerant. Which statement helps to explain why dichlorodifluoromethane is chemically
inert?
A
The carbon-fluorine bond energy is large.
The carbon-fluorine bond has a low bond polarity.
Fluorine is highly electronegative.
Fluorine compounds are non-flammable.
The primary structure of a protein is held together by hydrogen bonds.

Which of the following amino acids would not allow the formation of hydrogen bonds in
the primary structure of an -helix?
Capsaicin is the compound which gives the hot taste to chilli.
capsaicin
What is the number of sp2 and sp3 carbon atoms respectively in a molecule of
capsaicin?
sp2
sp3
15
12
11
Compound Z, a dienone, is formed from 4-hydroxyphenol in a reduction process during

black-and-white photography.
Products A and B are obtained when Z is treated with HCN and a small amount of
NaCN.
What is the relative ratio of A and B formed and the optical activity of the final solution?
relative ratio
optical activity
no activity
shows activity
no activity
shows activity
SRJC/PRELIM 2010/P1/Q21
The structure of Ergocalciferol, also known as vitamin D2 is shown below:

HO
Ergocalciferol
How many optical isomers are present in this molecule?
A
B
C
D
8
12
64
Which of the following is NOT the product formed when butene reacts with IBr (aq)?
Br
OH I
OH Br
Br
When hot NaOH is added to compounds H and J, C6H5CH2OH and C6H5CH=CH2 are
formed respectively. What could compounds H and J be?b
H
J
CH2OCH2CH3
CH2CH2Br
A
CH2Br
B
CH2CH2Br
CH2OCH2CH3
CH2CH2OH
CH2Br
CH2CH2OH
Which one of the following will be formed when butane-1,3-diol is distilled with hot
alkaline potassium manganate (VII)?
A CH3COCH2CHO
B CH3COCH2COOH
C CH3CH(OH)CH2COO
D CH3COCH2COO
The following reagents were added to K and M and the observations were made:
Reagents
Observation
Alkaline aqueous iodine
Brown iodine decolourises for K but not M
Acidified potassium dichromate (VI) Green solution seen for K but not M
Aqueous bromine
M decolourise reddish brown bromine but
not K
What could be the structural formulae of K and M?
K
CH(OH)CH3
CH2CH(OH)CH3
CH2OH
OH
CH2CH2CH2OH
CH3C(OH)CH3
B
OH
CH(OH)CH3
OH
CH3C(OH)CH3
C
CH2OH
OH
CH2CH2CH2OH
CH2CH(OH)CH3
OH
OH
Compounds N and P are first reacted with hot aqueous NaOH followed by dilute HCl at
room temperature.
CH2Br
COOH
Br
CHBrCH3
CH2CH2Br
Compound N
Compound P
Which reagents could be used to distinguish the final products of N and P?

A
B
C
D
H2, Ni catalyst
Iodine in aqueous NaOH
Phosphorus pentachloride
Na metal
Compound Q can be converted to compound R in a sequence of steps.
Br
Br
CH3
O2N
C Br
O2N
CH3
CH3
C O C CH3
CH3
R

A The sequential conversion of Q to R involves a nucleophilic substitution
reaction, acidic hydrolysis and esterification.
B Compound Q must be converted into an alkene first in the first step of
conversion to compound R.
C Neutralisation occurs when aqueous sulfuric acid is added to Q and R
separately at rtp.
D When hot aqueous sodium hydroxide is added separately to compounds Q and
R, only compound Q gives a cream precipitate when added to silver nitrate
solution.
TJC/PRELIM 2010/P1/Q21
Which of the following synthetic routes does not produce ethanoic acid?
A
B
CH3CH(OH)CH3
CH3CH(OH)CH2CH3
aqueous alkaline iodine

heat
excess conc H2SO4
180oC
H+
r.t.p.
acidic K2Cr2O7
heat
C
D
alcoholic KCN
reflux
CH3Br
dil HCl
heat
[Ag(NH3)2]+
heat
CH3CHO
H+
r.t.p.
What reagent can be used to distinguish between the following isomers?

CO2H
CONH2
NH2
A
B
C
D
OH
Aqueous NaOH, heat

Na metal, room temperature and pressure
Aqueous bromine, room temperature and pressure
LiAlH4, dry ether, room temperature and pressure
The uncatalysed addition of HCN to a carbonyl group to give a cyanohydrin proceeds

by two steps.
Step I
- :CN +
H3CH2C
C
+
CN
H3CH2C
H3CH2C
C
H
A
B
C
D
O-
CN
Step II
CN
O:- +
CN
H3CH2C
OH
+ :CN
The rate equation for the formation of cyanohydrin is as follows.

Rate = k[CH3CH2CHO][CN-]
Step II is rate determining.
The reaction will proceed slower if small amount of NaOH is added.
A same product can be obtained by refluxing 1-chloropropan-1-ol with HCN.
The uncatalysed addition of HCN to propanone occurs at slower rate than that for
propanal.
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
CH2CH2OH
C
OH
O
H
CH2CO2H
D
OH
Which of the following shows the correct order of increasing acidity?
OH
<
CH3CH2OCOH
<
CH3CH2CO2H
<
CH3CHFCO2H
OH
CH3CH2OCOH
<
<
CH3CH2CO2H
<
CH3CHFCO2H
OH
CH3CHFCO2H
<
CH3CH2CO2H
<
CH3CH2OCOH
<
OH
CH3CHFCO2H
<
CH3CH2OCOH
<
CH3CH2CO2H
<
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?
A
B
C
D
CH3CH2CH2Cl + 2Br2 DBCP + 2HBr

CH2BrCHBrCH3 + Cl2 DBCP + HCl
ClCH2CH=CH2 + PBr5 DBCP + PBr3
CH2=CHCH2Cl + Br2 DBCP
-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
Major product X
H3C
H3C
CH3
The structure of the alkaloid ephedrine is shown below.

OH CH3
C
H
N
CH3
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.
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 C 4H9 and X the
halogen atom.)
H2O(l) + RX(l) + Ag+(aq) ROH(aq) + AgX(s) + H+(aq)
A
B
C
D
The rate of formation of cloudiness in the tubes was in the order RCl < RBr < RI. Why
is this?
The R-X bond polarity decreases from RCl to RI.
The solubility of AgX(s) decreases from AgCl to AgI.
The ionisation energy of the halogen decreases from Cl to I.
The bond energy of R-X decreases from RCl to RI.
A
B
C
D
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?
CH3CH=CHCH3
(CH3)2CHCH2OCH2CH3
CH3CH2CH(OCH3)CH2CH3
CH3CH2CH(CH3)OCH2CH3
VJC/PRELIM 2010/P1/Q18
-Caryophyllene is an odiferous sesquiterpene used by the cotton plant to attract the

male cotton boll weevil.
CH3
CH3
CH 2
CH 3
-Cary ophyl lene
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
Which type of reaction does the following compound not undergo?
HOCH2CH2COCH2
A
B
CO2H
C
D
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 H 2O.
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.
Which of the following compounds react with hot acidified KMnO 4 and
the resultant product

dinitrophenylhydrazine and PCl5?
A
formed will give a positive test with both 2,4C
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
B
0
1
C
D
2
3
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?
A
phenylmethanol
B
methanoic acid
C
phenylmethanol and phenol
D
phenylmethanol, phenol and methanoic acid
Enalapril is used to treat hypertension.

CH2CH2CHCO2CH2CH3
CO2H
NHCH(CH3)CONH
Enalapril
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.
Compound M can be synthesised as shown below.

O
HO
OH
Compound M
HOCH2 CH2CH=CH2
II
What are the reagents used for steps I, II and III?

I
II
III
M
III
H+/KMnO4(aq)
PCl5
NaOH(aq)
H+/KMnO4(aq)
PCl5
H2O
NaOH(aq), I2(aq)
HCl(aq)
OH/KMnO4(aq)
HCl(aq)
C
D
1.
2.
1.
2.
concentrated H2SO4
H2O
concentrated H2SO4
H2O
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?
R
S
T
U
CH3CH2CO2H
CH3CH2COCl
CH3CH2CONH2
CH3CHClCH2NH2
CH3CH2CO2H
CH3CH2COCl
CH3CHClCH2NH2
CH3CH2CONH2
CH3CH2COCl
CH3CH2CO2H
CH3CH2CONH2
CH3CHClCH2NH2
CH3CH2COCl
CH3CH2CO2H
CH3CHClCH2NH2
CH3CH2CONH2
Which compound decolourise brown bromine in the dark?

OH
CH3
NO2
CH2NH2
A
CN
CO2H
Cl
NH2
B
Which of the following pairs of protein segments has an interaction which is likely to be
broken due to a change in pH?
NH
O CH2
NH
+
NH3
CH
(CH2)4
CO
A
CO
and
NH
HS CH2
NH
CH
HS CH2
CO
B
CH
CH
CO
and
CH2
CH2
CH2
NH
NH
CH
O C
CH
CO
CO
and
NH
HO CH2
NH
CH
HS CH2
CO
CH
CO
and
YJC/PRELIM 2010/P1/Q21
The molecule which is not chiral is

A
H3C
C
HO
CH3
Br
NH2
Br
Br
Br
Br
Br
C
Br
COOH
H3C
NH2
Br
Br
The structural formula of an organic compound is as shown.

CH3 CH2 CH
CH CH2 CH2 CH3
CH3 CH2 CH2 CH2 COOH
The IUPAC name for this compound is

A
3-methyl-4-butyloctanoic acid
B
3-methyl-4-propyloctanoic acid
C
4-propyl-5-methyloctanoic acid
D
6-methyl-5-propyloctanoic acid
Consider the solubilities of the following compounds in water.

W CH3 CH COOH
Y
CH3CH(OH)CH3
NH2
X
CH3CH2OCH3
Z
CH3CH(OH)CH2OH
The order of increasing solubility of the compounds is
A
ZWYX
B
XYZW
C
YZXW
D
XWYZ
The compound least likely to be formed when gaseous ethene is bubbled into a
mixture of aqueous bromine and aqueous sodium chloride is
A
B
C
D
CH2BrCH2Br
CH2BrCH2OH
CH2BrCH2Cl
CH2ClCH2Cl
Cl2 was passed into methylbenzene under reflux. Which of the following
mechanistic step might occur?
A
CH 2
HCl
Cl
Cl
CH 2
CH Cl
Cl
CH3
H+
HCl
Cl
CH3
CH 2 Cl
CH 2 Cl
Cl+
CH3
One method of determining the protein content of a food is to determine its

nitrogen content. This is done by first converting the nitrogen to ammonium sulfate
and then to ammonia.Calculate the mass in grams of ammonia formed if all the
nitrogen in 1 mole of arginine is converted into ammonia.
Formula of arginine:
H
H2N
(CH 2)3 N
COOH
A
34 g
68 g
NH2
132 g
264 g
A dibromoalkane CH3CH2CHBrCHBrCH2CH3 was treated with excess alcoholic

potassium hydroxide. The main product would be
A CH3CH2CH(OH)CH(OH)CH2CH3
B CH3CH2CH2O-K+
C CH3CH=CH-CH=CHCH3
D CH3CH2CH=CHCH2CH3
JC/PRELIM 2010/P1/Q28
Bradosol is a compound used for the relief of sore throats. It is produced in the
following reaction.
CH3
O CH2 CH2 Br
C12H25
CH3
CH3
X
Y
The role of compound Y in this reaction is
A
an acid
O CH2 CH2 N C12H25

CH3
Bradosol
+
Br
B
C
D
a nucleophile
an electrophile
a reducing agent
Which reaction is not typical of carbonyl compounds?

H
H
C
H2
H
C
Pt
H2NOH
C=N-OH
H
C
CH3Br
H
C
OH-
HCN
OCH 3
Br
+ H2O
CHOH
OH
CN
A compound R was used for two experiments and the results as shown below.
No. Experiment
Results
I
II
stirred
with 1 chlorine atom was removed per molecule of R
cold NaOH(aq)
stirred with hot 2 chlorine atoms were removed per molecule of R.
NaOH(aq)
Which of the following compounds could be R?

A
C
Cl
COCH 2Cl
Cl
Cl Cl
Cl
CH CH CH3
CH
CHCH 2COCl
Cl
Cl
CHCH 2COCl
Cl
MCQ Section B
Which of the following is a suitable chemical test to distinguish the below two
compounds?
H3C
H3C
HO
X
1
2
3
OH
H3C
OCH 3
CH3
OCH 3
CH3
H3C
Cold dilute KMnO4

Hot acidified K2Cr2O7
Warm alkaline I2
Which compounds liberate ammonia when boiled with aqueous sodium
hydroxide?
1
CH3CH2CN
2
CH3CH2CONH2
3
CH3CH2CO2NH4
Which of the following statements are true for compound A?
1
2
3
It gives a orange precipitate with 2,4-dinitrophenylhydrazine.

It gives a silver precipitate with Tollens reagent.
It undergoes esterification with phenol.
Which of the following tests can be used to distinguish between the compounds
W and X?
Na metal
2
3
hot aqueous AgNO3

hot acidified K2Cr2O7
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
a saturated noncyclic diol
Which statements are true for an SN2 reaction?
1
One bond is broken before another bond is formed.
The formation of a transition state involves the collision of two molecules or ions.
A carbon atom in the transition state is bonded, either fully or partially, to five other atoms.
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 sp 3 hybridised to being sp2
hybridised?
1
CH2CH3
Cl2 in UV light
C(CH3)2I
NaOH (aq), heat
CH3
Br2 in the presence of iron
Saccharin is an artificial sweetening agent. It can be synthesised from methylbenzene through a
series of reactions as shown.
O
CH3
CH3
C NH
CH3
CO2H
SO2
SO2NH2
SO Cl
SO NH
2
saccharin
What types of reactions are involved in the series?
Condensation
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
CH3NH3+Cl
CH3CONH2
The diagram below shows the reaction pathway of one of the mechanisms in the reaction of
halogenoalkanes with aqueous potassium hydroxide.
What information could be deduced from the above diagram?

1
X represents the carbocation intermediate formed in the reaction.
2
Y represents the transition state of the rate determining step.
3
The diagram shows a two-step mechanism of a SN2 reaction.
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:
H
H
O
C
C
H
O
C
OH
base
H3C
C
H
O
CH2
C
H
hydrogen atom
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
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
2
3
It is likely to be more acidic than phenol.

It can react with ethanoyl chloride to form an ester.
It can react with 2,4-dinitrophenylhydrazine to give an orange precipitate.
Fluocortin is a glucocorticoid that is involved in the regulation of glucose metabolism.
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
2
3
Oxidation of Y produces an organic compound that reacts completely with 3 mol of

2,4-dinitrophenylhydrazine.
It has three chiral centres more than Fluocortin.
It can be distinguished from Fluocortin by using sodium carbonate.
Deuterium, D, is the 2H isotope of hydrogen.
Which of the reactions will give an organic product containing deuterium?
For the reaction:
(CH3)3SiCl + C2H5O
(CH3)3SiOC2H5 + Cl
Which of the following statements are likely to be true?
1
It involves nucleophilic attack by C2H5O.
2
Cl is displaced by C2H5O.
3
The oxygencarbon bond is not broken.
Which of the following is the same in both the optical isomers of lactic acid, CH3CH(OH)COOH?
H f
1
2
3
pKa
boiling point
The diagram shows some laboratory apparatus:
Which preparations could this apparatus be used for?

1
Bromoethane, from ethanol, sodium bromide and concentrated sulfuric acid.
2
Ethanal, from ethanol, sodium dichromate(VI) and sulfuric acid.
3
1,2dibromoethane, from bromine and ethene.
The use of Data Booklet is relevant to this question.
When exposed film from a camera is developed, one of the steps involves reacting the
lightactivated silver bromide crystals with aqueous alkaline hydroquinone.
Which of the following statements is true?

1
This is a neutralisation reaction.
2
Both the organic reactant and product will decolourise aqueous potassium
manganate(VII).
3
Hydroquinone acts as a reducing agent.
Which of the following statements are true regarding compound Z?
There is only one sp hybridised carbon atom in a molecule of Z.
2
3
A molecule of Z contains four bonds.

After Z reacts with LiAlH4, all the carbon atoms in the product formed are sp3
hybridised.
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)
Aqueous bromine, Br2(aq)
The diester R, which is used in perfumes, has the molecular formula C 7H12O4. 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
CH3CO2CH2CH2CO2CH2CH3
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
Acidified KMnO4
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
Isoelectric point
cysteine (cys)
alanine (ala)
5.05
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.
Histidine would migrate towards the cathode.
IJC/PRELIM 2010/P1/39
Consider the following reaction.
(CH3)3SiCl + CH3CH2ONa+
(CH3)3SiOCH2CH3 + Cl
Which of the following statements are likely to be true?

The reaction involves a nucleophilic attack by the ethoxide ion.
Chlorine is displaced by the ethoxide ion.
The carbon-oxygen bond is broken.
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?

Reaction I is an acid-base reaction.
The product of reaction I is (CH3)3CH.
Carbonyl compounds react with Grignard reagents via nucleophilic addition.
For the following reaction:
(CH3)3CSO2Cl + CH3CH2OH (CH3)3CSO3CH2CH3 + HCl
Which statements are likely to be true?
1
2
3
The CO bond is not broken.

Cl is displaced by CH3CH2O.
The reaction involves a nucleophile.
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
3
CH3CH2CH2CH2OH
(CH3CH2)2CHOH
Salicylic acid is an important compound in its medicinal and cosmetic uses.
Salicylic acid
Which compounds give salicylic acid on acid hydrolysis?
1
-aminobutyric acid and -aminobutyric acid are isomers.
-aminobutyric acid
-aminobutyric acid
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.
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
Which mixtures, on heating, produce an alkaline gas containing deuterium, D?
1
CH3CH2CONHCH3 and NaOD in D2O
2
(ND2H2)2SO4 and NaOD in D2O
3
C6H5CH2CN and DCl in D2O
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
retinal
Which of the following statements about retinal are correct?

1
The molecular formula of retinal is C20H28O.
2
It can react with NH2OH.
The structure of its cis isomer is
O
OH
Compound AOwas used in the following synthetic route.
NaCN, dil HCl
Cl
CH2
CH3
trace amount
of NaOH
Cl
Compound A
CH2
CH3
LiAlH4
dry ether
Compound C
CN
Compound B
Which statement is true regarding the synthetic route?

1
2
3
There are 3 sp3, 6 sp2 and 1 sp hybridized carbon atoms in Compound B.

The synthetic route involves addition and reduction reactions.
Compound B is optically active.
The reaction scheme below outlines the production of 1,4-diaminobutane from compound X.
KC N
compound X
in e th a n o l
NCCH2CH2CH2CH2CN
Which of the following could be compound X?

1
BrCH2CH2CH2CH2Br
2
HOCH2CH2CH2CH2O
3
CHOCH2CH2CHO
Safranal is a component of the yellow dyestuff saffron.
r e d u c tio n
NH 2(CH2) 6NH 2
1,4-diaminobutane
CH3
CH3 O
H
CH3
Safranal
Which of the following descriptions about safranal are correct?
1
It reacts with Tollens reagent.
2
It reacts with KCN in ethanol at 10 to 20 oC.
3
It has all atoms lying in the same plane.
The three compounds P, Q, and R shown below are important flavours in citrus fruits. These
compounds are much used in the food and perfume industries.

1
Q can be converted to R by using NaBH4 in methanol.
2
R can be distinguished from P and Q by reacting it with sodium metal.
3
P, Q and R form the same compound when reacted with cold aqueous KMnO4.
The following shows part of a protein structure.
Which of the following types of interaction is responsible for maintaining the tertiary structure of
the protein shown above?
1
ionic bond
2
hydrogen bond
3
van der Waals forces
The pKa values of the following compounds are given below.
Compound
H2CO3
CF3COOH
CH3CH2OH
pKa
6.4
0.2
16.0
10.0
OH
3.4
O2N
CH3O
COOH
NH3+
5.3
In which of the following acid-base reactions will the equilibrium favour the products over
the reactants?
OH
HCO3
COO
NH2
COOH
+
OCH3
NO2
CF3
OCH3
NO2
O
C
H2CO3
NH3+
OH
+ CH3CH2O
CF3
+ CH3CH2OH
Which products are formed when phenyl propanoate undergoes acidic hydrolysis in the
presence of water labeled with the 18O isotope?
1
2
3
CH3 CH2CO18OH
C6H518OH
C6H5CO18OH
The structures and pKa values of fumaric acid and maleic acid are given below:
HOOC
H
H
COOH
fumaric acid
pKa1
3.0
pKa2
4.5
HOOC
H
COOH
1.9
maleic acid

1
2
3
Maleic acid has a lower boiling point than fumaric acid as it can form intramolecular hydrogen bonding.
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.
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.
Consider the following reaction scheme.
CH3O
CH3CH2SH +
CH3CH2S +
CH2
CH2
CH3CH2S +
II
CH3OH
CH3CH2SCH2CH2O
O
CH3CH2SCH2CH2O + H2O
III
CH3CH2SCH2CH2OH + OH
Which of the following types of reactions are shown in reactions I, II and III?
1
oxidation
2
3
neutralisation
Ellagic acid is a phenolic acid which is found in abundance in strawberries and
raspberries. Ellagic acid can prevent colon and esophageal cancers and is thus often an
ingredient added into multi-vitamins.
Ellagic acid
1 mol of Ellagic acid reacts with 4 mol of sodium metal to produce 2 mol of
hydrogen gas.
Addition of aqueous bromine results in 2 mol of bromine reacting with 1 mol of
Ellagic acid.
On heating with aqueous sodium hydroxide, 2 mol of sodium hydroxide are used up
per mole of Ellagic acid.
When compound Y was heated with acidified potassium manganate(VII), a gas was
produced which gave a white precipitate when passed into limewater.
Which of the following could Y be?
CH3OH
C6H5CH2CH3
CH3CH2CHCH2
Which reagents will convert ethanol into bromoethane?
red phosphorus and bromine
sodium bromide and sulfuric acid
aqueous bromine
Which of the following pairs of reagents will give a water-soluble organic product when reacted
together?
CH3CH2COOH and LiAlH4
CH3CH2COOH and CH3CH2NH2
CH3CH2COCl and (CH3CH2)2NH
Which of the following statement(s) regarding alkyl halides is/are true?
1 Chlorofluorocarbons are suitable to be used as aerosol because it does not react with
the compounds that it is carrying and it is very volatile.
2
Chlorofluorocarbons are non-biodegradable because they are chemically inert.
Chlorofluorocarbons slowly diffuse towards the upper atmosphere where they are
cleaved into fluorine radicals by UV light.
Which of the following statement(s) is / are true when the compound below reacts with
hot aqueous H+?
ClOC
OCOCH3
COOCH3
1 White fumes are observed.

2 A white precipitate is observed.
3 Hydrolysis has taken place.
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
Propanone and hydrazine can react to form hydrazine derivatives as shown below:
H3C
H3C
C
H3C
NH2NH2
NNH2
H2O
H3C
The reaction involves addition reaction, followed by elimination. Which of the following are
possible steps in the reaction?
H3C
H3C
C
NH2NH2
H3C
NH2NH-
H3C
H3C
H3C
C
NH2NH2
H3C
H3C
H3C
H3C
C
H3C
NH2NH2
OH
C
NH2NH2
H3C
NHNH2
Which statements about the following reaction sequence are correct?
H
H
C
C
H
I
Br2 in CCl4
II
excess conc NH3
in sealed tube
III
2+
Cu (aq)
Compound X is 1,2-dibromoethane
Step II involves nucleophilic substitution
Step III involves ligand exchange
Which of the following reactions give products that do not rotate the plane of polarised light?
Propene reacted with bromine dissolved in organic solvent.
Ethanal reacted with HCN, trace NaOH, 10 20C.
3-chloro-3-methylhexane refluxed with aqueous KOH.
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
aqueous bromine
CH2=CHCH3
acidified KMnO4(aq)
CH3CH2Br
CH3CO2-Ag+
Fehlings solution
NaOH(aq)
alkaline aqueous iodine
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
O
N
NH2
OH
NH2
Which of the following statements about this compound are correct?

Z undergo nucleophilic substitution with chloroethane
One mole of Z can be hydrolyzed to produce 2 moles of amino acids
When an aqueous solution of Z at pH 3 is analysed by electrophoresis, it is found near
the anode
NO2
H2SO 4
+ HNO3
+ H2O
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
CH3CHO + HCN
NaCN
CH3
CH3CH(OH)CN
CH 2Br
uv light
+ Br2
+ HBr
Which reactions would produce benzene1,3dicarboxylic acid?

CN
+ aqueous H2SO4, reflux
CO2CH3
1
CH=CHCH3
+ hot acidified potassium manganate(VII)
CO2CH3
CH(OH)CH3
+ akaline aqueous iodine followed by acidification
COCH3
3
Psilcin 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
N
H
compound K
Which statements are correct for compound K?
1
It gives white fumes with CH3COCl.
2
It reacts with both aqueous acids and alkalis.
The nitrogencontaining group in the ring has a lower pKb than the nitrogen
containing group in the side chain.
A compound K reacted with phenylhydrazine to yield another compound with the

structure shown.
H3C
C N NH
H2C
C N NH
H
Which pairs of reagents would react with K when added to K separately?

1
Lithium aluminium hydride in dry ether and acidified K 2Cr2O7
2
Lithium aluminium hydride in dry ether and sodium
3
Lithium aluminium hydride in dry ether and alcoholic KCN
Benzene reacts with Br2 in the presence of FeBr3, forming bromobenzene via
electrophilic substitution. The elementary steps of the reactions are:
FeBr3 + Br2 FeBr4 + Br+
H Br
Br+
+
Br
H Br
+ H+
H+ + FeBr4 FeBr3 + HBr

Which conclusions can be drawn about the mechanism?
1
The reaction level diagram is
The transfer of electron is
The intermediate for the reaction is planar.
Br
In an artificial hip joint, the poly(ethene) cup for this joint is attached to the pelvic
girdle by bone cement. The formation of the cement is highly exothermic and
involves polymerisation of the structure shown below.
CH3
H2C
COOCH 3
Which statements about the reactions of this structure are correct?

1
It undergoes electrophilic addition.
2
It is readily hydrolysed in dilute H2SO4 and aqueous NaOH.
3
Its oxidised products are CH 3OH and CH3COCOOH when subjected to
acidified K2Cr2O7.

Organic MCQ 2010 ANS Updated 22-05-2013

Uploaded by

Document Information

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Organic MCQ 2010 ANS Updated 22-05-2013

Uploaded by

Copyright:

Available Formats

Topic 10: Organic Chemistry

How many stereoisomers are there in the

Bromine and iodine essentially do not react with methane.

Fluorine is so reactive that neither UV light or heat is needed.

The bond energy of RX decreases from RCl to RI.

The ionisation energy of the halogen decreases from Cl to I.

The RX bond polarity decreases from RCl to RI.

The solubility of AgX(s) decreases from AgCl to AgI.

form two moles of CHI3 in (i).

react with two moles of 2,4dinitrophenylhydrazine in (ii).

form one mole of CH3COCH2CH2OH and two moles of Ag in (iii).

ethanoyl chloride and water

propanal and 2,4DNPH

propene and bromine

methylbenzene and nitric acid

Which compound would be a product of its hydrolysis with aqueous NaOH?

Which of the following statements about this compound is correct?

It can dissolve in aqueous sodium hydroxide but not hydrochloric acid.

It decolourises aqueous bromine only in the presence of light.

Three moles of CH3COOH will react with one mole of Dopamine.

What was the sequence of the original peptide?

Both can be obtained by the dehydration of alcohols.

CH3CHClCHClCH3 and ClCH2CH2CH2CH2Cl

Time for precipitate to appear

The lattice energy becomes more exothermic from AgCl to AgI.

1 mol of Tyrosol will react with 2 mol of Na to give 1 mol of H 2.

ring is not involved in any of the following reactions.

It can undergo oxidation with hot acidified K 2Cr2O7.

complete combustion of ethene in air

It acts as a buffer in a solution of pH 13.

What helps to explain the shorter carbon-nitrogen bond length in formamide?

Which of the following statements about hydrocortisone is true?

When treated with NaBH4 in the presence of methanol, it forms a compound

Which reagent could be used to distinguish Loviride from Compound Z?

aqueous alkaline iodine

aqueous sodium hydroxide

hot acidified potassium manganate(VII)

Which of the following is likely to be a property of this compound?

It is readily soluble in water.

The molecules exist as cistrans isomers.

It is hydrolysed by hot dilute sulfuric acid to give an amine.

It requires 4 mol of hydrogen gas for reduction.

acyl chlorides and carboxylic acids

carboxylic acids and esters

amino acids and ammonium salts

amides and amino acids

It contains carbon, hydrogen and bromine.

Its structure is planar.

The product formed

The product formed

The product formed

The product formed is a violet complex.

Which one of the following reagents can be used to distinguish between

hot concentrated potassium manganate(VII)

hot acidified potassium dichromate

The type of reaction taking place in each of the steps is

CH3CO2H > CF3CO2H > C2H5OH > C6H5OH

What are the expected observations?

Warm with Tollens reagent

Which deduction about paracetamol can be made from this structure?

Which are the structures of P and Q?

Which of the following can be S?

A student carried out an experiment in the following steps.

Resulting mixture is shaken with an equal volume of an organic