What reactants combine to form 3-chlorooctane?
1 Answer
The following reactants combine to form 3-chlorooctane in POOR YIELD.
1. Oct-2-ene + hydrogen chloride
CH₃CH=CHCH₂CH₂CH₂CH₂ CH₃ + HCl → CH₃CH₂CHClCH₂CH₂CH₂CH₂CH₃
(+2-chlorooctane)
2. Oct-3-ene + hydrogen chloride
CH₃CH₂CH=CHCH₂CH₂CH₂CH₃ + HCl → CH₃CH₂CHClCH₂CH₂CH₂CH₂CH₃
(+ 4-chlorooctane)
3. Octane + hydrogen chloride + ultraviolet light
CH₃CH₂CH₂CH₂CH₂CH₂CH₂CH₃ + HCl → CH₃CH₂CHClCH₂CH₂CH₂CH₂CH₃
(+ 1-chloro-, 2-chloro-, and 4-chlorooctane)
And here are three combinations that give 3-chlorooctane in GOOD YIELD.
4. Octan-3-ol + hydrogen chloride
CH₃CH₂CHOH CH₂CH₂CH₂CH₂ CH₃ + HCl → CH₃CH₂CHClCH₂CH₂CH₂CH₂CH₃ + H₂O
5. Octan-3-ol + thionyl chloride + pyridine
CH₃CH₂CHOH CH₂CH₂CH₂CH₂ CH₃ + SOCl₂ + C₅H₅N → CH₃CH₂CHClCH₂CH₂CH₂CH₂CH₃ + SO₂ + C₅H₅NHCl
6. Octan-3-ol + phosphorus trichloride + pyridine
CH₃CH₂CHOH CH₂CH₂CH₂CH₂ CH₃ + PCl₃ + C₅H₅N → CH₃CH₂CHClCH₂CH₂CH₂CH₂CH₃ + H₃PO₃ + C₅H₅NHCl
In the last two cases, the pyridine acts as a base. It reacts as a base to neutralize the HCl as it forms.
Here’s a video on the preparation of alkyl halides from alcohols and thionyl chloride.
