Substitution Reactions (Leaving Cert Chemistry): Flashcards

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Substitution Reactions
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Definition of substitution reaction

One atom/group replaced by another atom/group in a molecule

Type of reaction alkanes typically undergo

Substitution reactions

What is a free radical?

Atom/group with an unpaired electron

Symbol used to represent free radicals

Dot (•) next to chemical symbol

What initiates free radical substitution?

UV light or heat

Define homolytic fission

Bond breaks, each atom gets one electron from the bond

4 steps of free radical substitution

Initiation, Propagation (×2), Termination

Initiation step for Cl2\text{Cl}_2 under UV light

Cl2→2Cl∙\text{Cl}_2 \rightarrow 2\text{Cl}^\bullet

Propagation step 2: hydrogen abstraction

Cl∙+CH4→HCl+CH3∙\text{Cl}^\bullet + \text{CH}_4 \rightarrow \text{HCl} + \text{CH}_3^\bullet

Propagation step 3: halogen abstraction

CH3∙+Cl2→CH3Cl+Cl∙\text{CH}_3^\bullet + \text{Cl}_2 \rightarrow \text{CH}_3\text{Cl} + \text{Cl}^\bullet

What happens in termination step?

Free radicals combine to form stable molecules

Evidence: unexpected product in chlorination

Ethane (C2H6\text{C}_2\text{H}_6) from methyl radicals combining

Effect of accelerators (e.g. tetraethyl lead)

Increase rate by providing more free radicals

Chlorination of methane equation

CH4+Cl2→CH3Cl+HCl\text{CH}_4 + \text{Cl}_2 \rightarrow \text{CH}_3\text{Cl} + \text{HCl}

Bromination of cyclohexane equation

C6H12+Br2→C6H11Br+HBr\text{C}_6\text{H}_{12} + \text{Br}_2 \rightarrow \text{C}_6\text{H}_{11}\text{Br} + \text{HBr}

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