Documente Academic
Documente Profesional
Documente Cultură
10
Both ethene and benzene react with bromine, but the mechanisms and the types of products
1 5 5 Both
ethene and benzene react with bromine, but the mechanisms and the types of products
of the two reactions are different.
of the two reactions are different.
H C
H2C2
CH
CH2 2
Br
Br2 2
Br
Br2 2
reaction I
reaction I
BrCH2CH2Br
no heat, no light, no catalyst needed BrCH2CH2Br
no heat, no light, no catalyst needed
reaction II
reaction II
heat and catalyst needed
heat and catalyst needed
Br
Br
+
+
HBr
HBr
(a) State the type of reaction undergone in each of reactions I and II.
(a) State the type of reaction undergone in each of reactions I and II.
reaction I
reaction I
..........................................................................................................................................
..........................................................................................................................................
reaction II
reaction II
..........................................................................................................................................
..........................................................................................................................................
[2]
[2]
UCLES 2008
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9701/04/M/J/08
9701/04/M/J/08
For
For
Examiners
Examiners
Use
Use
11
(b) In each of reactions I and II, the intermediate is a bromine-containing cation. In each
of the following boxes, draw the intermediate and use curly arrows to show how it is
converted into the product.
For
Examiners
Use
reaction I
product
intermediate
reaction II
product
intermediate
[4]
(c) Why do ethene and benzene differ in their reaction with bromine?
..........................................................................................................................................
.................................................................................................................................... [1]
[Total: 7]
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For
Examiners
Use
10
27
NO2
NO2
+ NO2
+ H+
(a) What reagents and conditions are needed for this reaction?
......................................................................................................................................[2]
+
(b) Write an equation showing how the electrophile NO 2 is formed from the reagents.
......................................................................................................................................[1]
(c) The nitration of methylbenzene produces mainly 2-nitromethylbenzene, whereas the
nitration of benzoic acid produces mainly 3-nitrobenzoic acid.
CH3
CO2H
NO2
NO2
3-nitrobenzoic acid
2-nitromethylbenzene
Use this information to suggest suitable intermediates G and H in the following two
2-stage syntheses of chlorobenzoic acids, and suggest suitable reagents for reactions
I to IV.
CO2H
Cl
II
CH3
I
G
III
CO2H
IV
Cl
H
reagents:
reaction I ................................................
reaction II ................................................
reaction IV ...............................................
[4]
[Total: 7]
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10
(a) All the carbon atoms in benzene lie in the same plane. This means that they are coplanar,
but this is not the case with cyclohexane.
benzene
cyclohexane
By rotating the molecule around its several CC bonds, all the carbon atoms in butane
can be made to lie in the same plane, but this is not the case with methylpropane.
H3C
CH2
H3C
CH3
CH2
CH3
H3C
butane
methylpropane
By considering the 3-dimensional geometry of the following five molecules, and allowing
rotations around CC bonds, decide whether or not the carbon atoms in each molecule
can be arranged in a coplanar fashion. Then place a tick in the appropriate column in
the table below.
H3C
C
H3C
A
CH3
O
C
CH3
H2N
CH3CH(OH)CO2H
NO2
C
CH3
compound
A
B
C
D
E
[3]
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11
(b) Methylbenzene can react with chlorine under different conditions to give the monochloro
derivatives F and G.
CH3
CH3
I
For
Examiners
Use
CH2Cl
II
Cl
F
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12
(c) Benzyl benzoate is a constituent of many perfumery products, and has also been
used in the treatment of the skin condition known as scabies. It can be made from
methylbenzene by the following route, which uses one of the chlorination reactions
from (b).
CH3
IV
III
V
CO2H
CH2OH
VI
O
C
CH2
O
benzyl benzoate
(i)
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For
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Use
13
(ii)
For
Examiners
Use
reaction Ill
..................................................................................................................................
reaction V
..................................................................................................................................
reaction VI
..................................................................................................................................
(iii)
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45
For
Examiners
Use
(a) State the reagents and conditions necessary to carry out this reaction.
..........................................................................................................................................
......................................................................................................................................[2]
(b) What type of reaction mechanism is this?
......................................................................................................................................[1]
(c) The reaction proceeds via two steps:
+ X+
NO2 + Z+
Y
(i)
(ii)
(iii)
(iv)
BILAL HAMEED
9701/4 O/N/02
9
(d) Some aromatic poly-nitro compounds are used in perfumes as artificial musks. An
example is Baur musk.
For
Examiners
Use
CH3
O2N
NO2
C(CH3)3
NO2
Baur musk
(i)
Draw the structural formula of the hydrocarbon that could be nitrated in order to
produce Baur musk.
(ii)
Suggest the structural formula of the compound formed by reacting Baur musk with
an excess of tin and concentrated hydrochloric acid.
[2]
[Total: 10]
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57
Predict
the products
of the
reactions
andand
draw
their
structures
in the
boxes
provided.
7
Predict
the products
of following
the following
reactions
draw
their
structures
in the
boxes
provided. ForFor
NoteNote
that that
the molecular
formula
of
the
final
product
is
given
in
each
case.
Examiners
the molecular formula of the final product is given in each case.
Examiners
Use
Use
C 2 +Clight
+ light
2
NaOH
NaOH
heat
heat
O
C8H
C10
8H10O
C 2 +CA2 C
+A
3 C 3
HNO
HNO
3 +3 +
H2SO
H2SO
4
4
55C
55C
C88C
H8O
C2O
C8H
N2N
KMnO
KMnO
4
4
+ OH+OH
+ heat
+ heat
CHCH
+ +
3OH
3OH
conc.
H
conc. H2SO2SO
4 4
+
thenthen
H+ H
heat
heat
C10CH1010HO104O4
[6][6]
[Total:
[Total:
6] 6]
UCLES 2010
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9701/41/M/J/10
13
(c) When heated with concentrated, acidified KMnO4(aq), one of the two alkenes L or M
produces the dicarboxylic acid N.
For
Examiners
Use
CO2H CO2H
N
(i)
(ii)
Suggest the structure of the product, P, of the reaction between the other alkene
you have drawn and hot concentrated acidified KMnO4.
P
(iii)
Suggest one chemical test that would enable you to distinguish between N and P.
reagent(s) ..................................................................................................................
observation ................................................................................................................
[3]
Suggest the mechanism of this 2-stage reaction by means of a diagram. Include all whole
or partial charges, and represent the movements of electron pairs by curly arrows.
[3]
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[Total: 12]
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10 10
65
There
are are
several
ways
of introducing
chlorine
atoms
into
organic
molecules.
State
5(a) (a)
There
several
ways
of introducing
chlorine
atoms
into
organic
molecules.
Statethe
the ForFor
Examiners
Examiners
reagents
andand
conditions
necessary
to carry
outout
thethe
following
transformations.
reagents
conditions
necessary
to carry
following
transformations.
Use
Use
transformation
transformation
C2HC4 2H4
H5Cl
C2HC52Cl
C2HC
2H5OH
5OH
H5Cl
C2HC52Cl
C2HC6 2H6
H5Cl
C2HC52Cl
C H
C2H4 2 4
C H Cl
C2H42Cl42 2
CH CO H
CH3CO32H 2
CH3
CH3
CH3
CH3
reagents
+ conditions
reagents
+ conditions
CH3COCl
CH3COCl
Cl
Cl
CH3
CH3
CH2Cl
CH2Cl
[6]
[6]
(b) (i) When treated with concentrated HNO3 + H2SO4 at 55 C, benzene produces
(b) (i) When
treated with concentrated HNO3 + H2SO4 at 55 C, benzene produces
nitrobenzene.
Outline the mechanism of this reaction. You should include all charges, and use
nitrobenzene.
curlythe
arrows
to represent
the reaction.
movement
of electron
pairs. all charges, and use
Outline
mechanism
of this
You
should include
curly arrows to represent the movement of electron pairs.
UCLES 2011
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9701/41/M/J/11
11
In aromatic substitution of monosubstituted benzenes, the orientation of an incoming
group depends on the nature of the group already attached to the ring.
For example, using the same reagents and conditions as in (i), methylbenzene and
benzoic acid produce the following nitro compounds.
CH3
CH3
CO2H
For
Examiners
Use
CO2H
NO2
NO2
(ii)
methylbenzene
benzoic acid
Using this information as an aid, suggest a structure for compound C in the following
synthesis of 3-bromobenzoic acid.
CO2H
CH3
step 1
step 2
Br
C
(iii)
step 1
[6]
[Total: 12]
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