Core Practical 6: Investigate the chlorination of 2-methylpropan-2-ol

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Overview:

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Procedure:

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Procedure:

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Learning Tips;

  • the hydroxyl group in an alcohol can be replaced by a halogen

  • PCl5 can be used as an alternative reagent to HCl to make a chloroalkane

  • 50% concentrated sulphuric acid and potassium bromine (which makes HBr in situ) can be used to make a bromoalkane (+heat)

  • red phosphorus with iodine can be used to make an iodoalkane (+heat)

  • the purity of a liquid can be checked by measuring its boiling temperature

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Write an equation for the reaction of 2-methylpropan-2-ol with concentrated hydrochloric acid.

CH3C(OH)(CH3)CH3 + HCl → CH3CCl(CH3)CH3 + H2O

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What is removed from the crude product when it is shaken with sodium hydrogencarbonate solution? Write an equation for any reaction that occurs.

HCl is removed.

HCl + NaHCO3 → NaCl + CO2 + H2O

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2-methylpropan-2-ol has a boiling temperature of 82 degrees C and is soluble in water. 2-chloro-2-methylpropane has a boiling temperature of 51 degrees C and is insoluble in water. Explain these differences.

  • both 2-methylpropan-2-ol and 2-chloro-2-methylpropane have london forces and permanent dipole - permanent dipole forces.

  • however 2-methylpropan-2-ol also contains hydrogen bonding due to the hydroxyl group

  • this means that the 2-methylpropan-2-ol can hydrogen bond with water molecules

  • these hydrogen bonds are similar in strength to those between water molecules

  • so it is soluble in water

  • hydrogen bonds are relatively much stronger than pd-pd interactions and london forces therefore it takes much more energy to overcome them and so 2-methylpropan-2-ol has a higher boiling point than 2-chloro2-methylpropane