Electrochemistry

Determine Products of Electrophilic Addition Reactions

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The electrophile (species with + or δ+) is added to the C=C first
The electrophile is added to the C with more H (Markonikov’s Rule)
Presence of competing nucleophiles can lead to a mixture of products

Question. When alkenes are reacted with mixed halogens e.g. I―Cl, which atom is the electrophile; which atom is added to the C=C first?

Answer. Compare the electronegativity of the halogens. The less electronegative element is the electrophile; it is added first and to the C with more H.

Example (for 1+2):

I is less electronegative compared to Cl
I is added first and to the C with more H

Example (for 3):

Reagent used is Br₂ (aq) [c.f. Br₂ (in CCl₄)]
There are two possible nucleophiles in the 2nd step: Br^– and H₂O
A mixture of products would be obtained

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Electrochemistry