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
Nucleophilic substitution of primary halogenoalkanes
- 3 things to know
- Components 1 and 2
Overview
Mechanism by which hydroxide ions react with a primary halogenoalkane and leaving group.
What you need to know
Answer each one before you reveal it.
Name the mechanism by which hydroxide ions react with a primary halogenoalkane.
Describe the second curly arrow in the reaction of hydroxide ions with bromoethane.
Questions from this subtopic
Each one with the model answer underneath.
- 1
Explain why the carbon atom bonded to the halogen in a halogenoalkane carries a partial positive charge.
Model answer
The halogen is more electronegative than carbon, so it draws the bonding pair towards itself and leaves the carbon atom electron deficient.
- 2
Name the mechanism by which hydroxide ions react with a primary halogenoalkane.
Model answer
The mechanism is nucleophilic substitution.
- 3
Why is the hydroxide ion described as a nucleophile?
Model answer
It carries lone pairs of electrons on the oxygen atom and a negative charge, so it donates a pair to an electron-deficient carbon.
- 4
Describe the first curly arrow in the reaction of hydroxide ions with bromoethane.
Model answer
An arrow runs from a lone pair on the oxygen of the hydroxide ion to the δ+ carbon atom, showing the new carbon-oxygen bond being formed.
- 5
Describe the second curly arrow in the reaction of hydroxide ions with bromoethane.
Model answer
An arrow runs from the middle of the C—Br bond to the bromine atom, showing heterolytic fission that releases a bromide ion.
- 6
From which direction does the nucleophile approach the carbon atom in this reaction, and why?
Model answer
It approaches from the side opposite the halogen, because that keeps it as far as possible from the electron-rich leaving group.
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