Wheel of Epoxides

An epoxide or oxirane is a triangular cyclic ether, a structure that has substantial ring strain, making epoxides highly reactive, more so than other ethers.


An attack by a variety of nucleophiles gives multiple products.



Wheel of Epoxides: Click/tap to enlarge the image

Reaction type -> Product (on the infographic):

  1. Deoxygenation -> Alkene
  2. Hydrolysis -> Glycol
  3. Solvolysis -> Î²─alkoxy alcohol
  4. (Hydrohalic acid) -> Halohydrin
  5. 1. Reduction (LAH) 2. Hydrolysis -> Alcohol
  6. 1. Reduction (LiAlD4) 2. Hydrolysis -> Î²─Deuterated alcohol
  7. 1. Hydroboration or (AlD3) 2. Hydrolysis -> Alcohol or Î²─Deuterated alcohol
  8. 1. Reduction (DIBAL) 2. Hydrolysis -> Alcohol
  9. Grignard reaction or (1. Phenyl lithium 2. Hydrolysis) -> Î²─Aryl alcohol
  10. Grignard or Gilman reaction -> β─Alkyl alcohol
  11. 1. (Lithiated 1,3-dithiane) 2. Hydrolysis -> Î²─(1,3-Dithianyl) alcohol
  12. Grignard reaction -> Î²─Alkynyl alcohol
  13. 1. (20 amine, cat.) 2. Hydrolysis -> Î²─Dialkylamino alcohol
  14. 1. (Ammonia) 2. Solvolysis -> Î²─Amino alcohol
  15. (Sodium azide) -> Î²─Azido alcohol
  16. (Sodium/Potassium cyanide) -> Cyanohydrin
  17. 1. (Sodium thioalkoxide) 2. Hydrolysis -> Î²─Alkylsulfanyl alcohol
  18. 1. (Sodium hydrosulfide or Potassium thioacetate) 2. Hydrolysis -> Î²─Sulfanyl alcohol
  19. 1. (Sodium alkoxide) 2. Hydrolysis -> Î²─Alkoxy alcohol
  20. 1. (Sodium hydroxide) 2. Hydrolysis -> Glycol

LAH = Lithium aluminum hydride, DIBAL = Diisobutylaluminum hydride

What other wheel(s) 🛞 of organic reactions would you like to see ❓Let Chemaficionado know in the comments below or at mychemistryhomework@gmail.com❗

References:

(1)    Roman A. Valiulin, ChemInfoGraphic. ChemInfoGraphic. https://cheminfographic.wordpress.com.

(2)    Brown, C.; Ford, M. Higher Level Chemistry, 2nd ed.; Pearson Education: Harlow, Essex, 2014.

(3)    Ncert. Chemistry : Textbook for Class XI - Part.II; National Council Of Educational Research And Training: New Delhi.

(4)    Graham, T. W.; Fryhle, C. B.; Snyder, S. A. Organic Chemistry.; Hoboken, Nj John Wiley Et Sons, Inc, 2016.

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