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Relative reactivity of the haloalkanes

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

Overview

Recall questions on the carbon-halogen bond enthalpies, the silver nitrate rate experiment, and why bond strength rather than polarity decides the rate.

What you need to know

Answer each one before you reveal it.

Your recallNot started
Numbers

How do the carbon-halogen bond enthalpies rank, how do the electronegativity differences compare, and why one water bath?

Key term

Why does a silver halide precipitate appear, what colour is each, and which appears first?

Key term

What happens if a fluoroalkane is tested, why does bond strength rather than polarity decide the rate, and which of 1-chloropropane and 1-iodopropane is hydrolysed faster?

Key term

Why is silver nitrate added rather than simply warming the haloalkanes with water alone?

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    What two competing explanations are offered for the different reactivities of the haloalkanes?

    Model answer

    Either the strength of the carbon–halogen bond, measured by its bond enthalpy, or the polarity of that bond.

  2. 2

    Which haloalkane would the bond-polarity argument predict to be the most reactive, and why?

    Model answer

    The fluoroalkane, because C–F is the most polar bond and so leaves the carbon atom with the largest δ+ charge for a nucleophile to attack.

  3. 3

    Which haloalkane does the bond-enthalpy argument predict to be the most reactive?

    Model answer

    The iodoalkane, because C–I is the weakest carbon–halogen bond and therefore breaks most easily.

  4. 4

    Given C–F 467, C–Cl 346, C–Br 290 and C–I 228 kJ mol⁻¹, rank these bonds by how easily they break.

    Model answer

    C–I breaks most easily, then C–Br, then C–Cl, and C–F is hardest of all to break.

  5. 5

    Calculate how much weaker the C–I bond is than the C–Cl bond.

    Model answer

    346 − 228 = 118 kJ mol⁻¹.

  6. 6

    Calculate the difference in bond enthalpy between C–F and C–I.

    Model answer

    467 − 228 = 239 kJ mol⁻¹.

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