OCR A-Level Chemistry B H433
Development of Practical Skills in Chemistry
Elements of Life
Developing Fuels
Elements From the Sea
The Ozone Story
What's in a Medicine?
The Chemical Industry
Polymers and Life
Oceans
Developing Metals
Colour by Design
Chemical Literacy
Mathematical Skills in Chemistry
The Ozone Story
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.
Why does a silver halide precipitate appear, what colour is each, and which appears first?
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?
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
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
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
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
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
Calculate how much weaker the C–I bond is than the C–Cl bond.
Model answer
346 − 228 = 118 kJ mol⁻¹.
- 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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