Naming Epoxides

Introduction

• Epoxides, also known as oxyranes, are molecules with two carbons bound to an oxygen, forming a heterocyclic compound.
• Two naming methods:
  1. Prefix "epoxy" per IUPAC rules or using the puzzle piece approach.
  2. Suffix "oxyrane."

Naming Method 1: Prefix "Epoxy"

• Basic Epoxide:
  • Identify and highlight the parent chain with the longest carbon chain.
  • Example: 2 carbon epoxide = 1,2-epoxyethane
  • Prefix 1,2-epoxy: Oxygen bound to carbons 1 and 2.
• Substituted Epoxide:
  • Numbering starts to give the lowest number to the epoxide.
  • Example: 3 carbon epoxide = 1,2-epoxypropane
  • 3 carbon chain = propane; epoxy = 1,2-epoxy.

Naming Method 2: Suffix "Oxyrane"

• Basic Oxyrane:
  • No substituents: simply "oxyrane."
• Substituted Oxyrane:
  • Methyl substituent: "methyl oxyrane."
  • No need to specify which carbon when methyl is the only substituent.

More Substituted Examples

• Example 1:
  • Count longest carbon chain.
  • Number to give lowest substituent number.
  • Example: Butane structure with methyl = 2,3-epoxy-2-methylbutane
• Using Oxyrane Method:
  • Unique numbering: Oxygen is 1, more substituted carbon is 2.
  • Multiple methyl groups = 223 trimethyl oxyrane.

Larger Molecules with Epoxides

• Recommendation: Use epoxy method.
• Identify longest chain, typically branching downwards.
• Example: 9 carbon chain with chlorine and methyl groups.
  • Name: 1-chloro-2-3-epoxy-7-methyl-nonane.

Epoxide on a Ring

• Parent chain is the ring.
• 6-carbon ring = cyclohexane.
• Epoxy on carbons 1 and 2.
• No need to include numbers if no other substituents.
  • Name: epoxycyclohexane.

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