"The Alcohol Substitution March"
(to the tune of "The Mickey Mouse Club March")

If you have an alcohol but want a halide, then
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Take off the OH group and put on halogen
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HCl! (For Cl!) HBr! (For Br!)
And hydroiodic acid for I-I-I-I!
Come along and substitute and we shall sing again:
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First the acid gives is proton to the oxygen.
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Water leaves and what's left is a carbocation.
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It won't last! (It won't last!) What it does! (What it does!)
Is add on the ion of a hali-i-i-ide!
Halide is the nucleophile in substitution
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This reaction's really fast with tertiary ion.
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Secondary will need heat, harsher conditions then.
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Primary! (Hardly works!) You need heat! (Lots of heat!)
The acid must be HBr or H-I-I-I.
And the mechanims is concerted. That is when
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by Thomas Ott
Oakland University, Rochester MI