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Question
Chemistry
Posted 5 months ago
7. Symbiosis
A demonstration of the "effect of substitution"

If CH3Cl\mathrm{CH}_{3} \mathrm{Cl} and CCl3H\mathrm{CCl}_{3} \mathrm{H} are mixed CH4\mathrm{CH}_{4} and CCl4\mathrm{CCl}_{4} will result. Why?
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Answer from Sia
Posted 5 months ago
Solution
1
Identify the reaction type: The reaction described is a halogen exchange or a free radical substitution reaction
2
Explain the mechanism: The reaction likely proceeds via a radical chain mechanism, where chlorine radicals generated from either CH3Cl\mathrm{CH}_{3}\mathrm{Cl} or CCl3H\mathrm{CCl}_{3}\mathrm{H} can abstract hydrogen from the other compound to form CH4\mathrm{CH}_{4} or CCl4\mathrm{CCl}_{4} respectively
3
Discuss the 'effect of substitution': The 'effect of substitution' refers to the reactivity of different hydrogen atoms in a molecule towards radical substitution. In CH3Cl\mathrm{CH}_{3}\mathrm{Cl}, the hydrogen atoms are less shielded by electron-withdrawing chlorine atoms, making them more reactive. In CCl3H\mathrm{CCl}_{3}\mathrm{H}, the single hydrogen is more shielded and thus less reactive
Answer
When CH3Cl\mathrm{CH}_{3}\mathrm{Cl} and CCl3H\mathrm{CCl}_{3}\mathrm{H} are mixed, a radical chain reaction can occur, leading to the formation of CH4\mathrm{CH}_{4} and CCl4\mathrm{CCl}_{4} due to the abstraction of hydrogen atoms by chlorine radicals.
Key Concept
Radical chain mechanism
Explanation
The reaction between CH3Cl\mathrm{CH}_{3}\mathrm{Cl} and CCl3H\mathrm{CCl}_{3}\mathrm{H} involves a radical chain mechanism where chlorine radicals abstract hydrogen atoms from the other molecule, leading to the formation of CH4\mathrm{CH}_{4} and CCl4\mathrm{CCl}_{4}. The 'effect of substitution' influences the reactivity of the hydrogen atoms in these molecules.

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