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2.2.1 ALCOHOLS
(oxidation and esterification reactions)
Name
..
Mark
../59
Paddington Academy
....%
Grade
1.
The ethanol can be oxidised to form either ethanal, CH3CHO (Fig. 1), or
ethanoic acid, CH3COOH (Fig. 2).
w a te r
out
110
100
90
80
70
60
50
40
30
20
w a te r
out
10
e
a
p
d
th a n o l
n d a c id ifie d
o ta s s iu m
ic h r o m a te ( V I)
10
e
a
p
d
w a te r
in
th a n o l
n d a c id ifie d
o ta s s iu m
ic h r o m a te ( V I)
w a te r in
d is tilla te
heat
ic e - w a te r
m ix tu r e
w a te r b a th
a t 6 0 C
Fig. 1
Fig. 2
The boiling points of ethanol, ethanal and ethanoic acid are given in the table
below.
boiling point / C
CH3CH2OH
CH3CHO
CH3COOH
21
118
(ii)
why the organic product is likely to be ethanoic acid if the apparatus shown
in Fig. 2 is used.
................................................................................................................
................................................................................................................
[2]
Paddington Academy
(b)
Write a balanced equation for the oxidation of ethanol to ethanoic acid. Use [O] to
represent the oxidising agent.
.........................................................................................................................
[2]
[Total 6 marks]
2.
(ii)
H
C
C H 3C H 2C H
C H 2O H
com pound E
[3]
(iii)
Paddington Academy
3.
(a)
H 2O
o r g a n ic p r o d u c t
(i)
State a suitable
catalyst. ..................................................................................
[1]
(ii)
Identify compound Y.
[1]
(b)
(ii)
[1]
[Total 4 marks]
4.
(a)
(ii)
State the colour change you would see during this oxidation.
from ................................................. to ..................................................
[1]
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(b)
A sample of the butanal from (a) was analysed using infra-red spectroscopy. The
infra-red spectrum contained an absorption in the region 16801750 cm1 but did
not contain a broad absorption in the region 25003300 cm1.
Refer to the Data Sheet for Chemistry provided.
What does the absorption in the region 16801750 cm1 indicate?
(i)
................................................................................................................
[1]
(ii)
................................................................................................................
[1]
(iii)
The reaction in (a) was carried out using distillation and not reflux.
Explain why.
................................................................................................................
................................................................................................................
[2]
[Total 7 marks]
5.
Citronellol, C10H20O, occurs naturally in both rose and geranium oils. The structural
and skeletal formulae of citronellol are shown below.
C H
C H
C
H 3C
CH
CH
C H
C H
C H
C H
s tru c tu r a l fo r m u la
(a)
O H
O H
s k e le ta l f o r m u la
Paddington Academy
(b)
State which of the two functional groups you named in (a) is:
1
(ii)
(iii)
Draw the skeletal formula of the organic product formed when bromine is
added to citronellol.
[1]
tr a n s m itta n c e
(iv)
[1]
Paddington Academy
(c)
(ii)
(iii)
6.
Lavandulol, C10H18O, is a fragrant oil which is found in lavender. The structural and the
skeletal formulae of lavandulol are shown below.
CH
C
H 3C
H
C
C
H
C
O H
C H
C
H 3C
O H
H
C
H
s tr u c tu r a l fo r m u la
(a)
(i)
s k e le ta l fo r m u la
(ii)
Paddington Academy
(b)
(c)
Lavandulol could be converted into an ester X, which is also found in lavender oil.
O
C
O
C H
ester X
State a reagent and a catalyst that could be used to form ester X from lavandulol.
reagent ............................................................................................................
[1]
catalyst ............................................................................................................
[1]
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(d)
(i)
(ii)
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7.
Predict two fragment ions that you would expect to see in the mass spectrum of
butan-1-ol and state the m/z value of each ion.
.........................................................................................................................
.........................................................................................................................
[2]
(ii)
Paddington Academy
10
8.
Analyse and interpret this information to determine a possible structure for compound X.
Show all your working.
[Total 5 marks]
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11