The reaction of each of the following molecules with Cl2 results in the formation of a product that contains dichloroalkane. Rank the reaction rates for each of these compounds with Cl2, fastest to slowest :

Engineering

Chemistry

Test of Alkenes and alkynes

Question

The reaction of each of the following molecules with Cl₂ results in the formation of a product that contains dichloroalkane. Rank the reaction rates for each of these compounds with Cl₂, fastest to slowest :

I, II, III, IV, V

III, II, V, I, IV

V, II, IV, I, III

IV, II, V, I, III

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Addition of chlorine to an alkene is an electrophilic addition reaction. Electron donating groups bonded to alkene increases reactivity and electron-withdrawing group decreases the reactivity.

Compound IV is most reactive because of electron-donating resonance +M effect of –NH group at the para position.

Compound II has slightly less reactivity because –NH group is on meta position to alkene substituent. Its effect is negligible in compound I and III as not directly linked to the benzene ring.

While compound III is least reactive because of electron withdrawing resonance effect of C = O group present at a para position has a higher effect than on meta position in compound I.

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