CP4 Hydrolysis of Halogenoalkanes

Student Name Claudia Manchado Date 06/03/2023

CPAC Criteria Y W N
CPAC 2: Applies investigative approaches and methods when using
instruments and equipment
2c) Identifies and controls significant quantitative variables where
applicable, and plans approaches to take account of variables that cannot
readily be controlled.

CPAC 3: Safely uses a range of practical equipment and materials

3a) Identifies hazards and assesses risks associated with these hazards,
making safety adjustments as necessary, when carrying out experimental
techniques and procedures in the lab or field.

CPAC 5:

Researches, references and report

5b) Sources of information are cited demonstrating that research has taken
place, supporting planning and conclusions.

Subject Specific Criteria Y W N

1 use appropriate apparatus to record a range of measurements (to include
mass, time, volume of liquids and gases, temperature)

2 use water bath or electric heater or sand bath for heating

4 use laboratory apparatus for a variety of experimental techniques,

including:

• titration, using burette and pipette

• distillation and heating under reflux, including setting up glassware

using retort stand and clamps

• qualitative tests for ions and organic functional groups

• filtration, including use of fluted filter paper, or filtration under reduced

pressure

11 safely and carefully handle solids and liquids, including corrosive, irritant,
flammable and toxic substances

Grade Awarded Comments

 CORE PRACTICAL 4: Investigate the hydrolysis of halogenoalkanes

Aim: To investigate the relative rates of hydrolysis of primary, secondary and tertiary halogenoalkanes and
of chloro-, bromo-, and iodoalkanes.

Variables:
Independent: alkanes
Dependent: Time taken for solution to become cloudy
Controlled: temperature (ice baths), quantity of ethanol, use a pipette, tightness of bung, same number of
drops of haloalkanes, start timer at same times, drops silver nitrate,

Safety:

Chemical Safety hazard Measures

1-chlorobutane - Highly ammable (1) (2) (3) (4) - Keep away from heat
1-bromobutane (5) - Keep container tightly closed
1-iodobutane - Could be fatal if ingested - Wear eye protection

Ethanol - Flammable - keep away from heat

- Wear gloves
Silver nitrate - Corrosive
- Transfer in a tray

- Use water from a kettle rather than hot

Hot water - Can cause burns
bunsen ame

Equipment:
- 250 cm3 beaker
- 12 test tubes with bungs
- 1-chlorobutane label orange
- 1-bromobutane label pink
- 1-iodobutane label purple
- 2-bromobutane label yellow
- 2-bromo-2-methylpropane label green
- silver nitrate solution
- 15 cm3 ethanol
- dropping pipettes
- two 10 cm3 measuring cylinder
- stop clock
- Labels for test tubes
- kettle

fl
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 Method:

Part 1
1. Set up a water bath. Fill the 250 ml beaker up to the three quarters mark with water, at around 30 °C.
2. Fill three test tubes each with 5 cm3 of ethanol. Now add four drops of 1-iodobutane to the rst tube,
four drops of 1-bromobutane to the second tube and four drops of 1-chlorobutane to the third tube. Label
the tubes.
3. Loosely place a bung in each test tube and place the test tubes in the water bath.
4. Pour 5 cm3 of silver nitrate solution into three clean test tubes.
5. When the halogenoalkane–ethanol solutions have reached the temperature of the water bath, add the
silver nitrate solution to one of the halogenoalkane–ethanol solutions and replace the bung. Start the
stop clock as you do so.
6. Measure the time taken for the precipitate to appear. As soon as the solution becomes cloudy stop the
stop clock.
7. Repeat steps 5 and 6 for the other two halogenoalkanes.

Part 2
8. Repeat Part 1 using 1-bromobutane, 2-bromobutane and 2-bromo-2-methylpropane instead of the
other halogenoalkanes.

Analysis of results:

Halogenoalkane Time to condense (s) The rate of hydrolysis of C4H9I was the fastest.
Rate of hydrolysis of C4H9Br was slower than that of
1iodobutane 28
C4H9I.
1bromobutane 330 Rate of hydrolysis of C4H9Cl was the slowest.

1chlorobutane No reaction

The rate of hydrolysis was faster for tertiary, then secondary,

Time to Time to
Halogenoalkane then primary.
condense (s) condense (s)

1bromobutane 260 210

2bromobutane 26 49

2-bromo-2-
1 2
methylbutane

Questions:
1. Write an equation for the reaction of 1-bromobutane with water.
C4H9Br(aq) + 2 H2O(l) → C4H9OH(aq) + H3O+(aq) + Br−(aq).

2. In these reactions a precipitate forms. Identify the precipitate formed when the halogenoalkane is 1-
iodobutane.
AgI

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 3. Explain why ethanol is used in these reactions.

Becuase its cheap and dissolves haloalkanes

4. Explain why water is able to act as a nucleophile.

Due to the availability of lone pairs of oxygen atoms

5. Explain why water is used as the nucleophile rather than hydroxide ions?
If hydroxide was used, the precipitate would form immediately

6. Draw skeletal formulae for each of the halogenoalkanes used in this investigation (there are 5 of them).
Classify each halogenoalkane as primary, secondary or tertiary.

Primary

Primary

Primary

Secondary

Tertiary

Evaluation:

This experiment could have been improved with repeats for the rst step, as we only did it once.
Comparing our data to other experiments in the internet, we can observe that the results are similar, and
we can see the same trends in their results.

(6), (7)

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 References
1 https://www. shersci.com/store/msds?partNumber=AC447020010&productDescription=1-
CHLOROBUTANE%2C+99.5%25%2C+F+1LT&vendorId=VN00032119&countryCode=US&language
=en

2 https://www. shersci.com/store/msds?
partNumber=AC106770500&productDescription=bromobutane--thermo-
scienti ctrade&vendorId=VN00032119&keyword=true&countryCode=US&language=en

3 https://www. shersci.com/store/msds?partNumber=AC173435000&productDescription=1-
IODOBUTANE+98%+STABI+500ML&vendorId=VN00032119&countryCode=US&language=en

4 https://www. shersci.com/store/msds?partNumber=AC106785000&productDescription=2-
BROMOBUTANE,+98%+500ML&vendorId=VN00032119&countryCode=US&language=en

5 https://fscimage. shersci.com/msds/97870.htm

6 https://quali cations.pearson.com/content/dam/pdf/A%20Level/Chemistry/2015/teaching-and-
learning-materials/AS-and-A-level-Chemistry-Core-Practical-4-Hydrolysis-Student-Teacher-Technician-
Worksheets.pdf

7 https://ibchemistryblog.wordpress.com/2015/11/27/practical-29-halogenoalkanes/

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