Rates of Reaction of the Halogenoalkanes

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Rates of reaction of the halogenoalkanes

scientific knowledge and understanding:

Halogenoalkanes are classified as either primary, secondary or

tertiary. In primary halogenoalkanes the halogen atom is covalently

bonded to a carbon atom which is bonded to one other carbon, to two

other carbons in secondary and three others in tertiary.

Apparatus for a reflux

Increasing the size of the halogen atom in the halogenoalkane decreases

the bond strength, increasing the reactivity of the molecule, as the bond is

easier to break.

BOND

BOND ENTHALPY (kJ mol-1)

carbon-fluorine 467

carbon-chlorine 340

carbon-bromine 280

carbon-iodine 240

It can clearly be seen that the bond enthalpy (energy needed to break bond)

of the C-X bond decreases as we move down as we go from C-F to C-I.

Halogenoalkanes are volatile liquids. As they are organic, any reactions

they partake in are usually quite slow and therefore must be heated under

reflux. A reaction carried out under reflux is one in which a condenser is

positioned vertically in the neck of the reaction flask to prevent any of the solvent/reactant liquids from evaporating.

Halogenoalkanes do not mix with water, so must be dissolved in ethanol before

being treated with any aqueous solutions.

Nucleophilic substitution is a reaction in which an electron-donor atom in a

molecule is eliminated, and replaced by another which will form a stronger

covalent bond in the

concerned molecule.

Primary halogenoalkanes will undergo nucleophilic substitution with

the following mechanism (SN2):

Nu – Nucleophile X – Halogen atom

A nucleophile is an atom/molecule, which has a lone pair of electrons.

It bonds by ‘attacking’ an electron deficient carbon atom and donating

its free pair of electrons. A nucleophile will only displace a halogen

it if it forms a stronger bond with the carbon.

In this investigation I will be examining the rate of reaction of

chloroethane, bromoethane and iodoethane, by treating them with a

solution of silver nitrate in a mixture of ethanol and water, and

timing how long it takes for a silver halide precipitate to become

visible.

The faster the precipitate appears, the more reactive the

halogenoalkane.

Primary halogenoalkanes will be used, as they take longer to react

than secondary ...

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Dropping pipettes will also be used, to minimise any risk of contact

with these chemicals when transferring them to the required vessel.

Safety goggles, lab coat and surgical gloves must be worn at all times

during the experiment to reduce the risk of any contact between

chemicals and eyes/skin.

If any chemicals, are ingested wash mouth out and give a glass or two

of water. If vapour is inhaled, supply plenty of fresh air and keep

warm. If liquid is splashed on eye, flood with gently running tap

water for ten minutes, or spilt on skin or clothes wash the affected

area thoroughly and remove contaminated clothing.

In all cases tell the supervising teacher and seek medical attention.

If any chemicals are spilt on the floor/workbench inform the

supervising teacher immediately so that the spill can be dealt with

safely.

Sources

- www.answers.com/topic/nucleophilic-substitution-reaction

- http://www.teachmetuition.co.uk/glossary.htm

- B.Ratcliff, H.Eccles, D.Johnson, J.Nicholson, and J.Raffan (2000)

Chemistry 1, Cambridge University Press

> Chapter 7, Basic concepts in organic chemistry: page 91

> Chapter 12, Halogenoalkanes: pages 137-139

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