NAME

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CLASS

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DUE DATE

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SCHOOL

ASSIGNMENT SUB TOPIC 5.3: ALCOHOLS

Why have laws been introduced to prevent drink driving? Drinking alcohol impairs judgement, reduces
vigilance, slows reaction times and increases the effect of tunnel vision. The inability to see what is happening
on either side when looking straight ahead is called tunnel vision. With alcohol in the blood, sight angle is
diminished. This lack of vision causes collisions, with their tragic consequences, even though you may well
ask, Why did they not see this vehicle? The answer is that they did not! If you drink, dont drive.

1.

Alcohols are organic compounds with an OH group. It is called a hydroxyl group, not a hydroxide group. Why?
_______________________________________________________________________________

2.

(a)

Give systematic names for these alcohols:

(i)

CH3 CH2 CH2 CH2 OH

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(ii)

CH3 CH2 CHOH

CH3

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CH3

CH3 CH2 CHCH2 OH

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(iii)
(b)

(1)

(3)

Classify each as a primary, secondary or tertiary alcohol.

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3.

(3)

Like water, alcohols are capable of intermolecular hydrogen bonding.

(a)

What does this statement mean?

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(b)

(1)

What properties does the ability to hydrogen bond give to a compound?

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(2)

4.

(a)

Glucose solution was fermented under anaerobic conditions. The glucose solution was boiled and then
cooled before the yeast was added.

(i)

Why was the glucose solution boiled and then cooled before the yeast was added?

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(ii)

(1)

What does anaerobic mean?

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(iii)

(1)

Give one expected observation during the fermentation.

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(1)

(iv) Give one use of ethanol, apart from alcoholic drinks.

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(1)

5.

Ethanol is the starting material for a range of important organic chemicals. The reactions, which produce some of
these, are summarised below. The reagents and conditions for the reactions have not been included.
CH3CO2C2H5
A

CH3CHO
B

C2H5OH

CH3CO2H
C

State the reagents and conditions needed to bring about each of the reactions A to C above.
A

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6.

(6)

Propan-1-ol, C3H7OH, is refluxed with an acidified solution of potassium dichromate (VI) to produce propanoic acid.
The acidified potassium dichromate (VI) acts as an oxidising agent.
(a)

Explain what is meant by the term reflux.

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(b)

State what colour change takes place in the reaction mixture.

from ___________________________ to ____________________________

(c)

(1)

(2)

Write a balanced equation for the oxidation of propan-1-ol to propanoic acid. The oxidising agent can be
represented as [O] in your equation.

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(2)

Student note:
This graph shows the increase in the chances of having an accident with a person driving with increasing
levels of alcohol in the blood. Can you suggest why 0.05 % (50 mg/100mL) is taken for the legal limit?

7.

Ethanol is a very important material in the chemical industry and to the wine industry. It is made by two major
processes the fermentation of grape sugar and the hydration of ethene.

(a)

Outline the fermentation method for producing ethanol.

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(b)

(3)

Why does fermentation produce a maximum concentration of ethanol of no more than 15%?

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(c)

The product of fermentation consists of aqueous ethanol which contains a solid material. Suggest what this
solid could be.

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(d)

(1)

(1)

In the hydration method, ethene and steam are passed over a catalyst, at about 350C and 60 atm pressure.
This produces a conversion of about 8% per pass, with the unreacted gases being recycled.
(i)

Why is a catalyst used?

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(ii)

What is the source of the large amounts of ethene required?

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8.

(2)

The production of body odour often begins with secretions from glands called apocrine glands which are most
numerous in the armpits. Skin bacteria, which live in the armpits, use these secretions to produce energy and
many different waste products. Scientists have isolated one of these products, compound E, which is shown below.
Compound E can be oxidised to form compounds F and G.

(a)

(b)

Compound E contains two functional groups. Identify both functional groups and state how you could test for
each.
Functional group 1

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Test

________________________________________________________________

Observation

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Functional group 2

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Test

________________________________________________________________

Observation

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(6)

Suggest the structural formula of compound F.

(1)

9.

Compound A is an alcohol, which has several structural isomers.

(a)

Analysis of A shows that it contains 68.2% carbon and 13.6% hydrogen, by mass. Show that this information
is consistent with an empirical formula of C5H12O for A.

(3)
(b)

The empirical formula of A is also its molecular formula. Give the structural formula of an isomer of C5H12O
which is:
(i)

a primary alcohol;

(ii)

a secondary alcohol which has a branched carbon chain;

(iii) a tertiary alcohol.

(3)

(c)

Each of these alcohols reacts differently with a solution of potassium dichromate (VI) which has been acidified
with sulfuric acid. For each example in (b), give the structure of the organic product from this treatment. If
there is no product, say so.
(i)

from the primary alcohol

(ii)

from the secondary alcohol

(iii) from the tertiary alcohol

(3)

10. Before the introduction of infra-red (IR) spectroscopy to determine blood alcohol content of drivers, gas liquid
chromatography (GLC) was used.
The chromatogram shown gives the results of a GLC analysis of the first five straight chained primary alcohols. The
more volatile a compound the less its retention time.

(a)

Record, in table form, the name, the formula and retention time for each alcohol analysed.

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(5)

(b)

Estimate a retention time for hexan-1-ol

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(1)

In GLC analysis for BAC a doctor takes a blood sample and an exact amount of blood is mixed with a known
amount of a standard solution of propan-1-ol. Here is a chromatogram from such an analysis.

(c)

What is meant by the term, a standard solution?

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(d)

(2)

Why is a standard amount of propan-1-ol added to the blood?

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(c)

(3)

If the concentration of the propan-1-ol was 60 mg per 100 mL of solution should the driver be charged for drink
driving? Why is a simple yes or no not a sufficient answer?

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(3)

Student note:
In roadside random breath testing the police use fuel cells. At one electrode the alcohol in the breath
(which is in direct proportion to the amount consumed) is oxidized to ethanoic acid, while at the other
electrode oxygen is reduced to water. The higher the concentration of alcohol in the breath, the higher the
voltage of the cell.
If the reading shows close to the limit, or over the limit (0.05%), then the suspect is taken to a police station
for a more accurate determination of blood alcohol concentration, using an infra-red absorption
spectrometer.
A blood sample analysis, using gas-liquid chromatography, can give an even more accurate result.
These tests must be carried out within a time limit, usually under two hours, as the body will remove
alcohol at the rate of 0.01% per hour.

11. Various methods have been used to determine whether a driver of a motor vehicle has a blood alcohol
concentration (BAC) in excess of the legal limit (50 mg per 100 mL of blood).
(a)

The earliest method for detecting ethanol in breath was based on a reaction that produced a colour change:
orange dichromate (VI) ions react with ethanol to form green chromium (III) ions.
(i)

Give the structural formulae of two organic products that could be formed from ethanol by reaction with
acidified dichromate (VI) ions.

(2)
(ii)

Write a balanced half-equation for the conversion of dichromate (VI) ions, Cr 2O7
3+
ions, Cr (aq), in acid solution. What type of reaction is occurring?

2-

(aq),

into chromium (III)

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(b)

(2)

Another way of finding ethanol concentration in breath is by using an electrochemical cell containing a
phosphoric acid solution. At one electrode oxygen is reduced to water, whilst at the other ethanol is oxidised
to ethanoic acid.
(i)

Explain how measuring the ethanol concentration in breath can lead to a reliable estimation of its
concentration in blood.

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(ii)

(3)

Write a balanced half-equation for the reaction occurring at the electrode where oxidation occurs.

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(2)

Total

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ANSWERS SUB TOPIC 5.3: ALCHOHOLS

1.

2.

3.

4.

5.

6.

7.

8.

9.

10.

11.