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Reg. No. 200710217Z

Foundation Organic Chemistry Questions


Alkanes
1
.

2.

(a
)
(b
)

What is meant by the term optical isomerism?


Draw the structural formula of the alkane with the lowest Mr that can
exhibit optical isomerism.

N98 P1 Q7 (modified)
Alkanes find many uses in real life application. Two of these include their use
as fuels and aerosols.
(a
)

Alkanes are commonly used as fuel in the internal combustion of


engine, and branched chain alkanes with 8 to 12 carbon atoms per
molecule are preferred for this.
(i)

Draw the structural formula of the most highly-branched


compound with molecular formula C8H18;

(ii
)

Draw the structural formula of a singly-branched chiral


compound with molecular formula C10H22.

(ii
i)

Write a balanced equation for the complete combustion of


octane, C8H18. Assuming that air contains 20% O 2 by volume,
what volume of air (at r.t.p.) is needed to burn 100 g of
octane?

(iv State and explain one disadvantage that can arise from the
)
use of alkanes as fuels.
[8]
(b
)

(i)

When compared to CFCs, why are alkanes preferentially used as


aerosols?

(ii
)

State a disadvantage of using alkanes, such as butane, as


aerosols.

[2]

X and Y have a molecular formula of C4H9Br. X exhibits stereoisomerism but


Y does not.
Both X and Y can be formed from butane by the reaction shown below:
CH3CH2CH2CH3

X + Y

(a)

Name the type of reaction undergone and state the conditions for [2]
the above reaction.

(b)

Draw the structural formula of X and Y.

[2]

(c)

Describe the mechanism for the formation of X.

[3]

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3.

In the past, chlorofluorocarbons (CFCs) were commonly used as


aerosols. In light of the environmental concern posed by CFCs, alkanes
are now preferentially used as aerosols. Butane is one such alkane.

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(d)

State the type of stereoisomerism exhibited by X and draw [2]


diagrams to illustrate how X gives rise to its stereoisomerism.

(e)

Estimate the ratio in which X and Y might be formed.

(f)

Explain why the resultant reaction mixture does not show optical [1]
activity.

[1]

Multiple-Choice Questions
1.

2.

Which of the following is a propagation step in the reaction between methane


and chlorine?
A

Cl2 2Cl

CH3 + Cl CH3Cl

CH3 + HCl CH3Cl + H

CH3 + Cl2 CH3Cl + Cl

How are the oxides of nitrogen formed in a car engine?


N01 P3 Q19

4.

Oxidation of nitrogen by ethanol in petrol.

Reaction of nitrogen with oxygen.

Oxidation of nitrogen by carbon dioxide.

Reaction of nitrogen compounds in petrol with oxygen.

Methane reacts with chlorine in the presence of sunlight. Which statement


about the intermediates is correct?
A

They are more energetically stable than the reactants.

They are positively charged ions.

They combine to form HCl.

They contain an odd number of electrons.

Why does the reaction between propane and chlorine not give a high yield of
2-chloropropane?
N05 P1 Q22
A

A mixture of chlorine and propane cannot be prevented from exploding.

Disubstitution by chlorine takes place preferentially to monosubstitution.


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3.

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5.

The central carbon atom of propane is too weakly nucleophilic.

The chlorine replaces any of the hydrogen atoms in propane.

Use of the Data Booklet is relevant to this question.


On the basis of bond energies, what could be the products of the following
reactions?
CH3 + CH3CH2Cl
N08 P1 Q21
A
B
C
D

1, 2 and 3 are correct

1 and 2 only are


correct

2 and 3 only are


correct

1 only is correct

The boiling point of pentane and 2,2-dimethylpropane are 36 oC and 9 oC


respectively.

6.

7.

The molecule of 2,2-dimethylpropane is more compact than that of


pentane.

The covalent bonds in pentane are stronger than those in


2,2dimethylpentane.

The pentane molecule has more electrons and is therefore more


polarisable.
Alkanes can be prepared from iodoalkanes by heating under reflux with
sodium (in ether) according to the equation:
2RI + 2Na RR + 2NaI
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Which of the following suggested factors make a significant contribution to


this difference in boiling point?

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Which alkanes will be produced if a mixture containing equal amounts of


CH3CH2I (iodoethane) and CH3CHICH3 (2-iodopropane) is used?
JJC 08 Prelim P1 Q38
1

CH3CH(CH3)CH(CH3)CH3

CH3CH2CH(CH3)CH3

CH3CH2CH2CH3

Alkenes
For each of the following reactions
(i)
(ii
)
(iii
)

2
.

state the type of reaction,


state the conditions, and
write balanced equations (structures of the major product will be
sufficient).
(a 2,3-dimethylbut-1-ene and hydrogen
)
(b hex-2-ene and chlorine gas
)
(c 2-ethylbuta-1,3-diene and hydrogen iodide
)
(d pent-1-ene and steam
)
(e cyclohexene and potassium manganate(VII) [state 2 different reaction
)
conditions]
(f 2-bromobutane and potassium hydroxide to form alkene(s).
)

2-bromobut-2-ene reacts readily with bromine dissolved in inert organic solvent


at room temperature.
(a State the observations for the reaction.
)
(b Write a balanced equation for the reaction.
)
(c State and describe the mechanism involved in the reaction.
)
(d Identify the type of stereoisomerism displayed by (i) 2-bromobut-2-ene
)
and (ii) its product after bromination. Draw suitable diagrams to illustrate
the stereoisomerism.
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1
.

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3
.

Briefly describe a simple laboratory test to distinguish the following pairs of


hydrocarbons. State your observations for the tests and write equations for the
reactions.
(a 1-methylcyclohexane and 1-methylcyclohexene
)
(b propene and pent-2-ene
)

4
.

X is a hydrocarbon with molecular formula C7H14. It takes part in the following


reactions:
It decolourises aqueous bromine.
On addition of hot, acidified potassium manganate(VII) solution, butanone
and propanoic acid are formed.
Deduce the structure of X and give your reasons.

MCQ
5.

N97 P3 Q 23
Hydrogen bromide reacts with ethene to form bromoethane.
What is the best description of the organic intermediate in this reaction?

It contains carbon, hydrogen and bromine.

B
C
D

It has a negative charge.


It is an electrophile.
It is a free radical.
(

6.

J09 P1 Q 29
2-methylbuta-1,3-diene, CH2=C(CH3)CH=CH2 is used as a monomer in the
manufacture of synthetic rubbers.
Which compound would not produce this monomer on treatment with
concentrated sulfuric acid at 170oC?
A

(CH3)2C(OH)CH(OH)CH3

HOCH2CH(CH3)CH2CH2OH
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C
D

HOCH2CH(CH3)CH(OH)CH3
HOCH2C(CH3)(OH)CH2CH3
(
)

7.

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

and

H C

and

Br Br

Br OH

Br

Br ONO 2

Br

OH

ONO2

and

H D

Br OH

and

(
)

8.

A species of termite produces a chemical defence secretion which contains


the following molecule.

To help determine the structure of this compound, it is treated with acidified


hot concentrated manganate(VII) ions.
A

CO2

B
C

CH3COCH3
CH3COOH

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Which compound is not produced in this reaction?

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HOOCCH2CH2COCOOH
(
)

Arenes
Nitrobenzene can be formed from benzene.
(a
)
(b
)
(c
)
2
.

3
.

State the type of reaction which occurred.


Describe the mechanism of the reaction (using arrows to show movement
of electrons).

Ethylbenzene can undergo the following reactions.

(a
)

2
.

State the reagents and conditions required for this conversion.

(a
)
(b
)
(c
)
(d
)

(a
)

Ethylbenzene reacts with chlorine in reactions I and II under different


conditions to give two different substituted products.
(i State the conditions necessary for reaction I and II respectively.
)
(ii State the type of reaction which occurred in reaction I and II
)
respectively.
Give an outline of the mechanism in reaction I.
Give an outline of the mechanism in reaction II.
Ethylbenzene also reacts with hot acidified KMnO 4 to give compound X in
reaction
III.
Draw the displayed formula of X and state the type of reaction that
occurred.
A student proposes two possible routes for the synthesis of 4-nitrobenzoic
acid from methylbenzene.
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1
.

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(b
)

Which of the two routes give a greater yield of 4-nitrobenzoic acid?


Suggest how the following conversions can be carried out by giving the
reagents and conditions needed for each stage of the conversion, and the
structure of the intermediate.
(i benzene C 4-bromonitrobenzene
)
(ii methylbenzene D 3-bromobenzoic acid
)

Halogen Derivatives
A reaction scheme is shown below.

(a
)
(b
)
(c
)
(d
)

2
.

State the reagents and conditions and type of reaction for reactions I to III.
State the reagents and conditions and type of reaction for reactions A to
D.
Suggest the structural formula of compound Z.
Describe the mechanism in reactions C and E.

3bromo3methylhexane undergoes the following substitution reactions:


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1
.

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(a) Describe the mechanism in reactions I and II.


(b) Hence explain why the resulting mixture obtained from either reaction is optically
inactive.
3
.

Compare and explain the difference in the reactivity of the following groups of
halogenated organic compounds towards hydrolysis with aqueous NaOH.
(a chloroethane and chlorobenzene
)
(b chloroethane, bromoethane and iodoethane
)

4
.

Describe one test (reagents, conditions and observations) to distinguish the


following compounds:
chlorobenzene, chloroethane, iodoethane.

5
.

Compound K has molecular formula C3H7Cl. On refluxing K with aqueous


sodium hydroxide, it yields a compound L, C3H8O, which is oxidised by acidified
potassium dichromate (VI) to M, C3H6O. Compound M gives a yellow precipitate
with 2,4-dinitrophenylhydrazine reagent, but fails to give a precipitate with
iodine in strong alkali.
Deduce the structures of K, L and M, giving your reasoning.

Hydroxy Compounds
Predict the major product of the reactions by balancing the following
equations.
Indicate No Reaction if the reaction does not occur. State the type of
reaction undergone in each case.
(a
)
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1
.

(b
)
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(c
)
(d
)
(e
)
(f)
(g
)
(h
)

(i)
(j)
(k
)
(l)

(
m
)
(n
)
(o
)

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(p
)

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(q
)

2
.

(a
)

Draw the structure of the organic products and state the type of reactions
undergone when a compound with the formula

reacts with
(i) sodium,
(ii aqueous sodium hydroxide,
)
(iii phosphorus pentachloride,
)
(iv ethanoic acid, concentrated H2SO4, heat under reflux
)
(v ethanoyl chloride
)
(vi acidified K2Cr2O7, distil
)
(vi aqueous Br2
i)
(b State the observations for the reactions of the above compound with
)
reagents (iii), (vi) and (vii).

4
.

By means of a simple one-step test, distinguish the following pairs of


compounds.
(a phenol and phenylmethanol
)
(b butan-1-ol and 2-methylpropan-2-ol
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3. The ester formed between 3-methylbutan-1-ol and ethanoic acid contributes to


the flavour of ripe pears.
(a Draw the structural formula of the ester
)
(b What conditions and reagents would you use in the laboratory to make the
)
ester from the acid and the alcohol named above?
(c Draw the structural formulae of three primary alcohols that are isomers of
)
3-methylbutan-1-ol, labelling with an asterisk any chiral carbon atom they
contain.

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)
(c butan-1-ol and butan-2-ol
)
You should include in your answer

the reagents and conditions used

observations for each compound


5
.

A compound Y has molecular formula C8H10O and exists as a pair of optical


isomers. It reacts with phosphorus pentachloride to give HCl and gives a yellow
precipitate when aqueous alkaline iodine is added. Suggest a possible identity
for Y and explain your reasoning.

6
.

Explain why phenol is a stronger acid than ethanol and why 4-chlorophenol is a
stronger acid than phenol.

Carbonyl Compounds
Predict the product of the reactions by balancing the following equations.
State the type of reaction undergone in each case.
(a
)
(b
)
(c
)
(d
)
(e
)

(f)

(g
)
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.

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(h
)
2
.

Complete the following table by drawing the structural formulae of all organic
products (if any). State, if any, the observations of each reaction.
Reagent &
Conditions

2,4DNPH

Tollens
reagent,
heat

Fehlings
solution,
heat

alkaline I2(aq), heat

3.

For the following conversion, give the reagents and conditions for each step
and draw the structures of the intermediates.
(a CH3CH2OH A B CH3CH2COOH
)
(b CH3CH2OH C D CH3CH(OH)COOH
)
(c CH3COCH3 E CH3CHBrCH3
)

4.

Describe the mechanism of the addition of hydrogen cyanide to butanone.


Hence explain why the reaction between butanone and HCN produces an
equimolar mixture of two isomers.

5.

By means of a simple one-step test, distinguish the following pair of


compounds:
(a pentan-3-one and pentane
)
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CH3CHO

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(b pentan-2-one and pentan-3-one


)
(c pentan-3-one and pentanal
)
(d pentan-3-one and pentan-3-ol
)
You should include the reagents, conditions used and observations for each
tested compound.
6. A certain industrial cleaner and paint solvent was distilled to produce a single
compound D with straight carbon chain.
When D reacted with 2,4dinitrophenylhydrazine, an orange precipitate was
produced.
With alkaline aqueous iodine, D gave a yellow precipitate.
D did not react either with warm acidified potassium dichromate(VI) or with
aqueous bromine.
Reduction of D with hydrogen over a catalyst produced an equimolar mixture of
two isomers, E and F, with the molecular formula C5H12O.
Suggest the structural formulae for D, E and F and explain the reactions
involved.

Carboxylic Acid & its Derivatives

(a
)

Reactions I, II and III show three possible methods of preparing CH 3COOH.


For each reaction,
(i) give the reagents and conditions required.
(ii state the type of reaction undergone.
)
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.

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(b
)

Reactions IV to VII show some common reactions of CH3COOH.


(i)
(ii
)
(ii
i)

Suggest the reagent and condition required for reaction IV.


Draw the organic products A, B and C.
State the type of reaction undergone in reactions IV to VII.

2.

(a
)
(b
)
(c
)
(c
)

Suggest a possible reagent to convert R back to ethanoyl chloride.


Rank the following compounds in descending order of their ease of
hydrolysis
(i.e. conversion of the Cl group for the OH group) and explain your
reasoning.
CH3COCl
C6H5Cl
CH3CH2Cl

3-hydroxybutanoic acid has the structure below.

(a
)
(b
)

Name all functional groups in 3-hydroxybutanoic acid.


Draw the structure of the organic product that is likely to be formed with
3-hydroxybutanoic acid when reacts with the following reagents. State the
type of reaction undergone for each reagent used.
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3.

The above reaction scheme shows three common reactions for ethanoyl
chloride, CH3COCl. Write balanced equations for the conversion of
ethanoyl chloride to R, S and T.
Draw the displayed structure of U.

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(i)
(ii)
(iii
)
(iv)
(v)
(vi)
(vii
)
4.

5.

aqueous NaOH
acidified K2Cr2O7(aq), heat under reflux
CH3CH2OH, a few drops of conc. H2SO4, heat under reflux
ethanoyl chloride

How may the following conversions be carried out? State clearly the reagents
and conditions required in each step and state the structural formula of any
organic intermediate involved.
(a
)(b
)(c
)

CH3CH(CH3)OH A B CH3CH(CH3)CO2H
CH3CH(OH)CH3 C D (CH3)2C(OH)CO2H
CH3CO2H E F G CH3CH2CO2H

(a
)

Explain the following observations fully.


(i) Propanoic acid is a stronger acid than propanol
(ii Propanoic acid is a stronger acid than 2-methylpropanoic acid
)
(iii 2-hydroxypropanoic acid is stronger than propanoic acid.
)
How would you expect the acidity of 3-chloropropanoic acid to compare
with
that
of
2-chloropropanoic acid?

(b
)

6.

PCl5
HBr
sodium

Suggest methods by which the following compounds could be distinguished


from each other by chemical tests. The distinguishing of some of these pairs
may rely on a preliminary breaking-up of the compounds, and subsequent
testing of the reaction products.
(a
)
(b
)

Phenol and ethanoic acid


CH3COOCH(CH3)CH2CH3 and CH3COOC(CH3)3

7.

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(c
)
J92/P1/Q11
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Compound B, a diacid that occurs in apples and other fruits, has the following
composition by mass:
C, 35.8%
H, 4.5%
O, 59.7%
B reacts with ethanol in the presence of concentrated sulfuric acid under reflux
to give C, C8H14O5. Compound C evolves hydrogen gas when treated with
sodium metal and reacts with acidified potassium dichromate(VI) to give
compound D. Compound D produces an orange precipitate with 2,4dinitrophenylhydrazine but has no reaction with Fehlings or Tollens reagent.
(a Calculate the empirical formula of B.
)(b Suggest structures for compounds B, C and D and explain the reactions
)
described.
Organic Nitrogen Compounds
1
.

(a
)

(b
)

Reactions I and II show two possible methods of preparing ethylamine,


CH3CH2NH2.
(i) Give the reagents and conditions for each reaction.
(ii State the type of reaction undergone for reaction I and II.
)
Reactions III and IV show two reactions of ethylamine.
(i)
(ii
)
(ii
i)

State the type of reaction that occurred in reactions III and IV.

J02/P4/Q7(a)-(b) modified
Phenylamine is an important intermediate compound for the production of
dyes.

(a
)

phenylamine
Phenylamine can be synthesised from benzene in two steps as shown
below.
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2
.

Draw the structural formula of the organic product Z.


Give the reagent for reaction IV.

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Draw the structural formula of the intermediate Y and suggest reagents


and conditions for steps I and II.

2. (b
)

Phenylamine is a weak base.


(i)
(ii
)

(c
)
3
.

Write an equation showing phenylamine acting as a base.


Arrange the following amines in increasing order of basic strength and
explain your answer.

Draw the structure of the product formed when phenylamine reacts with
aqueous bromine.

How can the following conversions be carried out? State clearly the reagents
and conditions required in each step and identify, if any, the intermediate
formed.
(a CH2=CH2 A CH3CH2NH2
)
(b CH3CH2Cl B CH3CH2CH2NH2
)(c CH3COOH C CH3CONHCH2CH3
)

Proteins
4. There are three pKa values associated with glutamic acid: 2.1, 4.1 and 9.5.

5. Angiotensin II, a peptide consisting of eight amino acids, is involved in the


regulation of blood pressure. Partial hydrolysis of Angiotensin II gives the
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(a Make use of the pKa values to suggest the major species present in
)
solutions of glutamic acid with the following pH values.
pH 1
pH 3
pH 7
pH 11
(
Hence, suggest a value for the isoelectric point, pI, of glutamic acid.
b
)

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following 5 fragments as well as the individual amino acids.


argvaltyr
ilehispro
prophe
aspargval
valtyrile
Deduce the primary structure of Angiotensin II.
6
.

The following structure represents a portion of a protein molecule:

(a
)
(b
)
(c
)
(d
)

Name the type of linkage that links the amino acids in this protein.
What reagent and conditions could you use to hydrolyse this protein into
its amino acids?
Draw the structural formula of the three amino acids that would be
produced by hydrolysing this portion of the protein using the reagent
suggested in (b).
Amino acids exist as zwitterions in aqueous solution.
Draw the structural formula of the zwitterion formed from amino acid A,
and write equations to show how it can react as a buffer.

7. The formulae of three amino acids are given.

(d
)

What is understood by the term primary structure of a protein.


Draw the structure of a section of a protein with the amino acid sequence
glyproala.
With the aid of a diagram, describe how a polypeptide chain is held in the
shape
of
an
helix.
With the aid of a diagram, describe the pleated sheet structure of
protein which constitutes the main material of meat.

8. J02/P4/1 modified
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(a
)
(b
)
(c
)

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The tertiary structure of a protein is the overall threedimensional shape of a


polypeptide. There are four types of sidechain R group interactions which hold
the tertiary structure in its shape.
(a (i) The cysteine residues in a protein molecule can form disulfide bridges.
)
Illustrate this process by means of a chemical equation, given that the
formula of the side-chain of a cysteine residue is CH2SH.
(ii) Other than disulfide bridge, state the other three types of sidechain R
group interactions, illustrating your answer with suitable pairs of
amino acids given below. (Note: Draw diagrams to illustrate your
answer.)

(iii
)
(iv
)

(c
)

Rate of enzyme-catalysed reaction

Page14

(b
)

Which amino acid residues listed in (a)(ii) are likely to be on the outer
surface of a
watersoluble globular protein? Explain your answer.
Where, in the globular protein, will the other amino acid residues most
likely to be found? Suggest what type of R group interactions would
occur between these residues?
Explain, in chemical terms, how sidechain R group interactions are
broken by each of the following examples of denaturation. Identify which
type of sidechain R group interaction(s) is/are broken in each example.
By heavy metal ions such as Ag+
By extreme pH changes
Alanine is one of the common amino acids used in living cells to
synthesise enzymes, which can catalyse biochemical reactions. The
catalytic activity of an enzyme is determined by its tertiary structure.
The effect of temperature on the catalytic activity of the enzyme human
catalase is investigated and the result is as shown below.

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Reg. No. 200710217Z

37

60

Temperature/ oC

Page14

Explain why the catalytic activity of the catalase is lost at 60 C.

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