Eduqas A-Level Chemistry A410QS
Formulae and Equations
Basic Ideas About Atoms
Chemical Calculations
Bonding
Solid Structures
The Periodic Table
Simple Equilibria and Acid-Base Reactions
Thermochemistry
Rates of Reaction
The Wider Impact of Chemistry
Organic Compounds
Hydrocarbons
Halogenoalkanes
Alcohols and Carboxylic Acids
Instrumental Analysis
Redox and Standard Electrode Potential
Redox Reactions
Chemistry of the P-Block
Chemistry of the D-Block Transition Metals
Chemical Kinetics
Enthalpy Changes for Solids and Solutions
Entropy and Feasibility of Reactions
Equilibrium Constants
Acid-Base Equilibria
Stereoisomerism
Aromaticity
Alcohols and Phenols
Aldehydes and Ketones
Carboxylic Acids and Their Derivatives
Amines
Amino Acids, Peptides and Proteins
Organic Synthesis and Analysis
Specified Practical Work
Practical Skills and Techniques
Mathematical Skills in Chemistry
Halogenoalkanes
Bond polarity, bond enthalpy and the ease of substitution
- 3 things to know
- Components 1 and 2
Overview
Trend in carbon-halogen bond enthalpy down the group and why fluoroalkanes are almost completely unreactive towards nucleophiles.
What you need to know
Answer each one before you reveal it.
Explain why the C—F bond is the most polar of the four carbon-halogen bonds.
Place 1-chlorobutane, 1-bromobutane and 1-iodobutane in order of increasing rate of hydrolysis.
Questions from this subtopic
Each one with the model answer underneath.
- 1
Place the C—F, C—Cl, C—Br and C—I bonds in order of decreasing polarity.
Model answer
The order is C—F, then C—Cl, then C—Br, then C—I.
- 2
Explain why the C—F bond is the most polar of the four carbon-halogen bonds.
Model answer
Fluorine is the most electronegative element of the group, so it draws the bonding pair furthest away from the carbon.
- 3
State the approximate bond enthalpies of the C—F, C—Cl, C—Br and C—I bonds.
Model answer
They are about 467, 346, 290 and 228 kJ mol⁻¹ respectively.
- 4
Explain the trend in carbon-halogen bond enthalpy down the group.
Model answer
The halogen atom gets larger down the group so the shared pair is further from its nucleus and the overlap is poorer, which makes the bond weaker.
- 5
Place 1-chlorobutane, 1-bromobutane and 1-iodobutane in order of increasing rate of hydrolysis.
Model answer
The order is 1-chlorobutane, then 1-bromobutane, then 1-iodobutane.
- 6
Which factor, bond polarity or bond enthalpy, controls the rate of substitution of a halogenoalkane?
Model answer
Bond enthalpy controls the rate, because the carbon-halogen bond has to be broken for the reaction to happen at all.
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