Alcohols 3 QP

1 This question is about the six alcohols below.
butan-2-ol ethane-1,2-diol
2-methylpentan-3-ol 2-methylpropan-2-ol
propan-1-ol propan-2-ol
(a) Which alcohol is an example of a tertiary alcohol?
.............................................................................................................................................. [1]
(b) Draw the skeletal formula for 2-methylpentan-3-ol.
[1]
(c) Butan-2-ol and 2-methylpropan-2-ol are structural isomers.
(i) What is meant by the term structural isomer ?
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(ii) Draw another structural isomer of these two alcohols.
[1]
(d) Ethane-1,2-diol can be dissolved in water to act as an anti-freeze in car radiators.
Explain why ethane-1,2-diol is very soluble in water.
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PhysicsAndMathsTutor.com
(e) Ethane-1,2-diol is heated under reflux with ethanoic acid and a small amount of H2SO4
catalyst. Compound A is formed with molecular formula C6H10O4.
Draw the structure of compound A.
[2]
(f) Butan-2-ol is heated with H2SO4 catalyst.
• A mixture of three alkenes forms, B, C and D.

• The alkenes B and C are stereoisomers.
(i) Draw the structures of the two stereoisomers B and C.
[2]
(ii) What type of stereoisomerism is shown by B and C?
...................................................................................................................................... [1]
(iii) Draw the structure of the other alkene, D, that is formed in this reaction.
[1]
(g) Alcohol E is one of the following alcohols.
butan-2-ol ethane-1,2-diol
2-methylpentan-3-ol 2-methylpropan-2-ol
propan-1-ol propan-2-ol
A student oxidises alcohol E by heating under reflux with excess acidified potassium
dichromate(VI). An organic product F is isolated.
The mass spectrum of the alcohol E is shown below.
100
80
relative 60
intensity
40
20
0
10 15 20 25 30 35 40 45 50 55 60
m/z
The infrared spectrum of the organic product F is shown below.
100
transmittance
(%)
50
0
4000 3000 2000 1500 1000 500
wavenumber / cm–1
• Name or draw the structures of the alcohol E and the organic product F.
• Write an equation for the reaction of alcohol E with acidified potassium dichromate(VI).
Use [O] to represent the oxidising agent, acidified potassium dichromate(VI).
In your answer, you should make clear how each structure fits with the information given
above.
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[Total: 19]
2 (a) Compound B, CxHyO, can be oxidised to form a ketone
C.
0.035 mol of B has a mass of 2.59 g.
Compound B reacts with compound D, C3H6O2, in the presence of an acid catalyst to form
two compounds E and F.
• Calculate the molar mass of compound B.
• Give the structures of compounds B, C, D, E and F.
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(b) Compound G is a branched-chain organic compound that does not have E and Z isomers.
Elemental analysis of compound G gave the following percentage composition by mass:

C, 55.8%; H, 7.0%; O, 37.2%.
The mass spectrum and infrared spectrum of compound G are shown below.
Mass spectrum
100
X
80
60
relative
intensity
40
20 Y
0
10 20 30 40 50 60 70 80 90 100
m /z
Infrared spectrum
100
transmittance
(%)
50
0
4000 3000 2000 1500 1000 500
wavenumber / cm–1
• Calculate the empirical and molecular formulae for compound G.
• Write the formulae for the particles responsible for peak X and peak Y in the mass
spectrum.
• Draw the structure of compound G.
Explain fully how you arrive at a structure for compound G using all the evidence provided.
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[Total: 13]
3 Sulfuric acid is made from sulfur, oxygen and water in a three-stage process.
This can be represented by the following overall equation.
2S(s) + 3O2(g) + 2H2O(l) 2H2SO4(l)
(a) Explain why the overall process to make sulfuric acid has an atom economy of 100%.
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(b) A factory uses 51.4 tonnes of sulfur to manufacture 147 tonnes of H2SO4.
What is the percentage yield of H2SO4?
Give your answer to two significant figures. (1 tonne = 1 × 106 g)
percentage yield = ...................................................... % [3]
(c) One of the reactions involved in making sulfuric acid converts sulfur dioxide, SO2, into sulfur
trioxide, SO3.
2SO2(g) + O2(g) 2SO3(g) ΔH = −197 kJ mol−1
This reaction can be carried out at 450 °C and 3 atmospheres pressure in the presence of a
V2O5 catalyst.
Under these conditions the position of equilibrium is almost completely on the right-hand
side.
(i) A research chemist investigates this reaction.

He uses a temperature of 450 °C and 3 atmospheres pressure.
The research chemist does not use the catalyst.
Predict the changes, if any, on each of the following.
position of equilibrium .......................................................................................................
rate of backward reaction ............................................................................................. [2]
(ii) The temperature of the reaction mixture is increased to 600 °C.
State and explain what will happen to the position of equilibrium.
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(iii) The pressure of the reaction mixture is decreased to 2 atmospheres.
State and explain what will happen to the position of equilibrium.
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(d) Concentrated H2SO4 is used as an acid catalyst in the elimination of water from alcohols.
There are several alcohols that are structural isomers with the formula C5H11OH. When these
alcohols are heated with H2SO4 they form alkenes.
C5H11OH C5H10 + H2O
(i) Pentan-1-ol is a structural isomer of C5H11OH that is a primary alcohol.
Draw the structure of another structural isomer of C5H11OH that is a primary alcohol.
[1]
(ii) Pentan-2-ol is a structural isomer of C5H11OH that is a secondary alcohol.

Pentan-2-ol is heated with H2SO4.
Three alkenes are formed, L, M and N.
• L and M are stereoisomers.

• N is a structural isomer of the stereoisomers L and M.
Draw the structures for alkenes L, M and N.
alkene L alkene M
alkene N
[3]
(iii) One structural isomer of C5H11OH is an alcohol that cannot be oxidised by heating with
acidified potassium dichromate(VI).
Draw the structure of this alcohol.
[1]
[Total: 13]

Alcohols 3 QP

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1 This question is about the six alcohols below.

(a) Which alcohol is an example of a tertiary alcohol?

(b) Draw the skeletal formula for 2-methylpentan-3-ol.

(c) Butan-2-ol and 2-methylpropan-2-ol are structural isomers.

(i) What is meant by the term structural isomer ?

(ii) Draw another structural isomer of these two alcohols.

(d) Ethane-1,2-diol can be dissolved in water to act as an anti-freeze in car radiators.

Explain why ethane-1,2-diol is very soluble in water.

Draw the structure of compound A.

(f) Butan-2-ol is heated with H2SO4 catalyst.

• A mixture of three alkenes forms, B, C and D.

(i) Draw the structures of the two stereoisomers B and C.

(ii) What type of stereoisomerism is shown by B and C?

The mass spectrum of the alcohol E is shown below.

The infrared spectrum of the organic product F is shown below.

Use [O] to represent the oxidising agent, acidified potassium dichromate(VI).

• Calculate the molar mass of compound B.

• Give the structures of compounds B, C, D, E and F.

Elemental analysis of compound G gave the following percentage composition by mass:

• Draw the structure of compound G.

2S(s) + 3O2(g) + 2H2O(l) 2H2SO4(l)

What is the percentage yield of H2SO4?

Give your answer to two significant figures. (1 tonne = 1 × 106 g)

percentage yield = ...................................................... % [3]

2SO2(g) + O2(g) 2SO3(g) ΔH = −197 kJ mol−1

(i) A research chemist investigates this reaction.

Predict the changes, if any, on each of the following.

position of equilibrium .......................................................................................................

rate of backward reaction ............................................................................................. [2]

(ii) The temperature of the reaction mixture is increased to 600 °C.

State and explain what will happen to the position of equilibrium.

(iii) The pressure of the reaction mixture is decreased to 2 atmospheres.

State and explain what will happen to the position of equilibrium.

C5H11OH C5H10 + H2O

(i) Pentan-1-ol is a structural isomer of C5H11OH that is a primary alcohol.

(ii) Pentan-2-ol is a structural isomer of C5H11OH that is a secondary alcohol.

Three alkenes are formed, L, M and N.

• L and M are stereoisomers.

Draw the structures for alkenes L, M and N.

Draw the structure of this alcohol.

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