Practical Endorsement GCE Chemistry

PAG5 Synthesis of an organic liquid

5.1 Synthesis of a haloalkane
LEARNER

5.1 Synthesis of a haloalkane LEARNER

Introduction
You will be synthesising an organic liquid. The reaction you will be carrying out is the nucleophilic substitution of
an alcohol to make a haloalkane. The alcohol you are starting with is 2-methylpropan-2-ol. This reacts with
hydrochloric acid to make a haloalkane product:

In this reaction, the Cl ion from the hydrochloric acid acts as the nucleophile.

There are three stages to the procedure:

 assessing the risks involved in the procedure, then carrying out the reaction
 separating the product from the reaction mixture,
 purifying the product.

The practical procedure is unusual in that the reaction is carried out using a separating funnel as the reaction
vessel rather than a conical or round-bottomed flask. After the reaction is complete, the haloalkane product is
separated from the reaction mixture in the separating funnel. Finally, the haloalkane product is purified by
distillation.

Aims and Skills

 To synthesise and purify an organic liquid
 To use a separating funnel and distillation apparatus in an organic synthesis
 To carry out a risk assessment

Intended class time

 2 hours + preparation time to conduct the risk assessment

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 Practical Endorsement GCE Chemistry
PAG5 Synthesis of an organic liquid
5.1 Synthesis of a haloalkane
LEARNER

Chemicals
You are provided with the following:

Label Identity Hazard information

2-methylpropan-2-ol, Use CLEAPSS resources or similar to find this
2-methylpropan-2-ol
CH3CH(CH3)OHCH3(l) information

concentrated hydrochloric Use CLEAPSS resources or similar to find this

conc. HCl(aq)
acid, HCl(aq) information
5% w/v sodium
Use CLEAPSS resources or similar to find this
5% NaHCO3(aq) hydrogencarbonate
information
solution, NaHCO3(aq)
anhydrous sodium Use CLEAPSS resources or similar to find this
Na2SO4(s)
sulfate(VI) solid, Na2SO4(s) information

0.4 mol dm–3 aqueous nitric Use CLEAPSS resources or similar to find this
HNO3(aq)
acid, HNO3(aq) information

0.05 mol dm–3 aqueous Use CLEAPSS resources or similar to find this
AgNO3(aq)
silver nitrate, AgNO3(aq) information

Equipment
For the preparation and separation:
 balance accurate to two decimal places
 wash bottle with distilled/deionised water
 measuring cylinder (10 cm3)
 measuring cylinder (50 cm3)
 separating funnel with stopper (50 cm3)
 retort stand, boss and iron ring to support separating funnel
 small funnel
 conical flask (250 cm3) with mineral wool plug
 2 conical flasks (100 cm3)
 spatula
For the distillation:
 water bath, electric heater or sand bath
 retort stands, bosses and clamps
 anti-bumping granules
 Quickfit apparatus:
o pear-shaped or round-bottom flask (50 cm3)
o still head
o thermometer (10 – 110 °C) and Quickfit adaptor (or thermometer pocket)
o Liebig condenser and tubing
o receiver
 beaker (100 cm3)
 sample tube with lid + glass marker pen

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 Practical Endorsement GCE Chemistry
PAG5 Synthesis of an organic liquid
5.1 Synthesis of a haloalkane
LEARNER

Health & Safety

Before beginning the procedure, you must complete a risk assessment. This should:
 identify the hazard information and precautions for the chemicals you will be using and producing –
use CLEAPSS resources (Student Safety Sheets) or similar,
 consider the actions you will take during the procedure,
 plan the precautions you will take to minimise the risk.
Have your risk assessment approved by your teacher before beginning the procedure.

Procedure
Before starting your practical work, read the information below.
Decide how you will organise your practical work, and which observations you need to make and/or which
measurements you need to take. Ensure that you record all of your results in a suitable format.

Part 1: Preparation
1. Ensure that you are confident and safe in using a separating funnel for i) separation of mixtures and ii)
shaking reaction mixtures and releasing any resultant pressure.
2. Pour about 6.5 cm3 of 2-methylpropan-2-ol into a 10 cm3 measuring cylinder.
3. Measure the mass of the measuring cylinder and contents.
4. Pour the 2-methylpropan-2-ol into a 250 cm3 conical flask.
5. Measure the mass of the empty measuring cylinder and use this to record the exact mass of 2-
methylpropan-2-ol you have put in the separating funnel.
6. Using a 50 cm3 measuring cylinder, measure about 20 cm3 of concentrated hydrochloric acid.
7. Over a period of about 2 minutes, add the concentrated hydrochloric acid gradually to the 2-
methylpropan-2-ol in the conical flask.
8. Place a mineral wool plug into the neck of the conical flask and gently swirl the mixture every few minutes
for 20 minutes.

Part 2: Separation
1. Using a funnel, pour the reaction mixture into a separating funnel. Ensure the tap is closed.
2. Allow the separating funnel to stand until the two layers have separated.
3. Open the tap and run the lower aqueous layer into a clean 100 cm3 conical flask.
4. Slowly add 10 cm3 of 5% sodium hydrogencarbonate solution to the organic layer in the separating funnel.
5. Put the stopper in the funnel and shake the contents gently. Carefully release the pressure build-up in
the separating funnel.
6. Shake the contents more vigorously and again release the pressure.
7. Allow the two layers to separate, then remove the stopper and run off the lower aqueous layer as in Step
2 of Part 2.
8. Repeat steps 3–7 until no more gas is given off.
9. Add 10 cm3 of distilled water to the separating funnel and shake again.
10. Allow the layers to separate and then run off the lower aqueous layer – you can discard this layer.
11. Allow the organic layer to run into a clean 100 cm3 conical flask. This liquid contains the product of the
reaction.
12. Anhydrous sodium sulfate acts as a drying agent to remove any traces of water. Add small quantities (½
spatula measures at a time) to the organic liquid. Swirl between each addition to the flask until the liquid
is completely clear and the sodium sulfate no longer forms clumps.

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 Practical Endorsement GCE Chemistry
PAG5 Synthesis of an organic liquid
5.1 Synthesis of a haloalkane
LEARNER

Part 3: Distillation
1. Set up the distillation apparatus as shown.

2. Measure the mass of a clean, dry sample tube and lid.

3. Decant the impure organic product to the pear-shaped flask and add a few anti-bumping granules.
4. Heat the liquid in the pear-shaped flask gently with a small Bunsen Burner or spirit burner. Use a small
beaker to receive any liquid impurities which distil over.
5. When the temperature is close to 48 °C, use the sample tube to collect the liquid. The boiling point of the
product is 51 °C.
6. When the temperature rises above 53 °C (or there is almost no more liquid in the pear-shaped flask), stop
the distillation.
7. Put the lid on the sample tube and weigh it to find the mass of product collected.
8. In a test tube, add 3-4 drops each of the following, as a test for the presence of haloalkane:
a. product
b. ethanol
c. 0.4 mol dm–3 HNO3(aq)
d. 0.05 mol dm–3 AgNO3(aq).

Analysis of your results

1. Calculate the percentage yield of your reaction.
2. Describe and explain the reaction between the product and acidified silver nitrate solution.

Extension Opportunities
1. Why were you advised to add the hydrochloric acid dropwise, rather than in one go?
2. At the end of the reaction, what impurities contaminate the organic product? How are each of these
impurities removed?
3. How does the final distillation step allow a check to be made on the identity and purity of the organic
product?
4. Discuss the factors that can lead to a percentage yield less than 100%.
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 Practical Endorsement GCE Chemistry
PAG5 Synthesis of an organic liquid
5.1 Synthesis of a haloalkane
LEARNER

Records
As evidence for the Practical Endorsement you should have recorded evidence of all of your observations and
measurements. If you completed a risk assessment for this practical, you should also include this in your records.
All work should be clearly dated.

In addition, in preparation for the assessment of practical work in the written examinations and to help you
develop your understanding of the underlying chemical theory, you should complete the questions in the Analysis
and Extension Opportunities sections.

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 Practical Endorsement GCE Chemistry
PAG5 Synthesis of an organic liquid
5.1 Synthesis of a haloalkane
LEARNER

Risk Assessment

If you are not conducting your own risk assessment for this activity, read and use the information below before
starting this activity:

Label Identity Hazard information

DANGER
Highly flammable liquid and vapour.
2-methylpropan-2-ol,
2-methylpropan-2-ol Causes serious eye irritation. Harmful
CH3CH(CH3)OHCH3(l)
if inhaled. May cause respiratory
irritation.

DANGER
Causes severe skin burns and eye
concentrated hydrochloric damage. May cause respiratory
conc. HCl(aq)
acid, HCl(aq) irritation.
Wear splash-proof goggles/face shield
Wear chemical resistant gloves
5% w/v sodium
5% NaHCO3(aq) hydrogencarbonate Currently not classified as hazardous
solution, NaHCO3(aq)
anhydrous sodium
Na2SO4(s) Currently not classified as hazardous
sulfate(VI) solid, Na2SO4(s)
WARNING
0.4 mol dm–3 aqueous nitric
HNO3(aq) Causes skin irritation and serious eye
acid, HNO3(aq)
irritation
Currently not classified as hazardous at this
0.05 mol dm–3 aqueous concentration
AgNO3(aq)
silver nitrate, AgNO3(aq) Solutions cause skin to blacken and will stain
clothing and some bench surfaces.

Health and Safety

 Wear eye protection at all times.
 Take care not to touch any apparatus that is hot.
 Particular safety considerations during the procedure:

Part 1: Preparation
2. Pour about 6.5 cm3 of 2-methylpropan-2-ol into a 10 cm3 measuring cylinder. (CARE: Keep reagent bottle
closed when not in use. Keep away from naked flames. Avoid contact with your skin and do not inhale
the vapour).
6. Using a 50 cm3 measuring cylinder, measure about 20 cm3 of concentrated hydrochloric acid. (CARE:
Corrosive. Wear chemical resistant gloves, avoid contact with your skin and work in a fume cupboard).

Part 2: Separation
2. Allow the separating funnel to stand until the two layers have separated. (CARE: The product is Highly
flammable and harmful).
5. Put the stopper in the funnel and shake the contents gently. Gas will be produced so the pressure inside
the separating funnel must be released. (CARE: Ensure the stopper is firmly held in place when the

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 Practical Endorsement GCE Chemistry
PAG5 Synthesis of an organic liquid
5.1 Synthesis of a haloalkane
LEARNER

separating funnel is inverted, the nozzle is pointing away from yourself and others, and you open the
tap gradually to release the pressure).
6. Shake the contents more vigorously and again release the pressure. (CARE: As step 5 in Part 2).

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