OCR A-Level Chemistry H432
Foundations in Chemistry
Bonding and Structure
Periodic Table and Energy
Enthalpy Changes
Chemical Equilibrium
Basic Concepts of Organic Chemistry
Core Organic Chemistry
Alkenes
Organic Synthesis
How Fast?
Physical Chemistry and Transition Elements
Acids, Bases and Buffers
Redox and Electrode Potentials
Transition Elements
Aromatic Compounds
Organic Chemistry and Analysis
Spectroscopy
Core Organic Chemistry
Nucleophilic substitution and carbon-halogen bond strength
- 2 things to know
- Components 02 and 03
Overview
Recall questions on the mechanism step by step, and on why the C-F bond is hardest and the C-I bond easiest to break.
What you need to know
Answer each one before you reveal it.
Why does the C-I bond break most readily, and how does bond strength relate to the rate of hydrolysis?
Questions from this subtopic
Each one with the model answer underneath.
- 1
In the nucleophilic substitution mechanism of a primary haloalkane with aqueous alkali, what does the hydroxide ion donate to the carbon atom?
Model answer
The hydroxide ion donates an electron pair (lone pair) to the carbon atom.
- 2
What new bond forms during the nucleophilic substitution of a primary haloalkane with hydroxide ions?
Model answer
A new carbon-oxygen bond forms.
- 3
How does the carbon-halogen bond break during nucleophilic substitution of a primary haloalkane?
Model answer
The carbon-halogen bond breaks heterolytically.
- 4
What is the fate of the halogen after the carbon-halogen bond breaks in nucleophilic substitution?
Model answer
The halide ion leaves as the leaving group.
- 5
In the mechanism for nucleophilic substitution of a primary haloalkane, where does the first curly arrow originate and where does it point?
Model answer
The first curly arrow originates from the lone pair on the hydroxide ion and points to the carbon atom.
- 6
In the mechanism for nucleophilic substitution of a primary haloalkane, what does the second curly arrow represent?
Model answer
The second curly arrow shows the movement of the electron pair from the carbon-halogen bond to the halogen atom.
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