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Properties and nucleophilic substitution of haloalkanes

  • 5 things to know
  • Components 01, 02 and 03

Overview

Recall questions on why ethanol is added as a solvent, the boiling point trend, and the equations for hydrolysis by hydroxide, water and ammonia.

What you need to know

Answer each one before you reveal it.

Your recallNot started
Process

Why is ethanol added when a haloalkane meets an aqueous reagent, how does haloalkane flammability compare with alkanes, and why do boiling points rise from CH₃F to CH₃I?

Numbers

What are the equations for bromoethane with hydroxide ions and with water, and what does 1-bromopropane give?

Numbers

Why is water a poorer nucleophile than hydroxide, what is the equation for bromoethane with excess ammonia, and why must the ammonia be in excess?

Key term

Why does a fluoroalkane resist all of these substitution reactions?

Key term

What is the leaving group when a haloalkane is hydrolysed, and what does it take with it?

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    Why is the carbon of a C–Cl bond δ+?

    Model answer

    Chlorine is more electronegative than carbon, so it draws the bonding pair towards itself and leaves the carbon partially positive.

  2. 2

    Why are haloalkanes attacked by nucleophiles?

    Model answer

    The δ+ carbon atom attracts species that carry a lone pair of electrons.

  3. 3

    Are haloalkanes soluble in water? Explain.

    Model answer

    They are essentially insoluble, because they cannot form enough attractions with water molecules to make up for the hydrogen bonds that would have to be broken between the water molecules.

  4. 4

    In what kind of solvent do haloalkanes dissolve readily?

    Model answer

    They dissolve in organic solvents such as ethanol or hexane.

  5. 5

    Why is ethanol added when a haloalkane is reacted with an aqueous reagent?

    Model answer

    Ethanol mixes with both the haloalkane and the water, giving a single mixture in which the reagents can actually meet.

  6. 6

    How does the flammability of haloalkanes compare with that of alkanes?

    Model answer

    Haloalkanes are much less flammable, and the heavily halogenated ones such as CF₂Cl₂ do not burn at all.

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