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2.
(a
)
(b
)
N98 P1 Q7 (modified)
Alkanes find many uses in real life application. Two of these include their use
as fuels and aerosols.
(a
)
(ii
)
(ii
i)
(iv State and explain one disadvantage that can arise from the
)
use of alkanes as fuels.
[8]
(b
)
(i)
(ii
)
[2]
X + Y
(a)
Name the type of reaction undergone and state the conditions for [2]
the above reaction.
(b)
[2]
(c)
[3]
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3.
(d)
(e)
(f)
Explain why the resultant reaction mixture does not show optical [1]
activity.
[1]
Multiple-Choice Questions
1.
2.
Cl2 2Cl
CH3 + Cl CH3Cl
4.
Why does the reaction between propane and chlorine not give a high yield of
2-chloropropane?
N05 P1 Q22
A
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3.
5.
1 only is correct
6.
7.
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CH3CH(CH3)CH(CH3)CH3
CH3CH2CH(CH3)CH3
CH3CH2CH2CH3
Alkenes
For each of the following reactions
(i)
(ii
)
(iii
)
2
.
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1
.
3
.
4
.
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?
B
C
D
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.
CO2
B
C
CH3COCH3
CH3COOH
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HOOCCH2CH2COCOOH
(
)
Arenes
Nitrobenzene can be formed from benzene.
(a
)
(b
)
(c
)
2
.
3
.
(a
)
2
.
(a
)
(b
)
(c
)
(d
)
(a
)
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1
.
(b
)
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.
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1
.
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
.
5
.
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
)
(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
.
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)
(c butan-1-ol and butan-2-ol
)
You should include in your answer
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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1
.
(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
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.
5.
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CH3CHO
(a
)
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1
.
(b
)
2.
(a
)
(b
)
(c
)
(c
)
(a
)
(b
)
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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.
(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
)
(b
)
6.
PCl5
HBr
sodium
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
)
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
.
2. (b
)
(c
)
3
.
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.
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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
)
(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.
(d
)
8. J02/P4/1 modified
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(a
)
(b
)
(c
)
(iii
)
(iv
)
(c
)
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(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.
37
60
Temperature/ oC
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