Author
Home > Science > What is the Difference Between Enols Enolates and Enamines?

Guilherme Mazui

•3 minutes to read

What is the Difference Between Enols Enolates and Enamines?

🆚 Go to Comparative Table 🆚

Enols, enolates, and enamines are three different types of organic compounds that exhibit distinct structural and chemical properties. The key differences between them are:

  1. Enols: Enols contain a hydroxyl group with an adjacent C=C double bond and are formed by combining an alkene group with an alcohol group. They are reactive structures because they occur as intermediate compounds in chemical reactions.
  2. Enolates: Enolates are derived from enols and are the conjugated bases of enols. They are formed by removing a hydrogen atom from the hydroxyl group of the enol.
  3. Enamines: Enamines contain an amine group adjacent to an alkene group. They are formed by the condensation of aldehydes or ketones with secondary amines and are considered to be the nitrogen analogues of enols. The chemical reactivity of enolates and enamines is almost similar, and they are moderately nucleophilic due to the additional electron density from the hydroxyl group or the amine group, respectively.

In summary, enols have a hydroxyl group with an adjacent C=C double bond, enolates are the conjugated bases of enols, and enamines have an amine group adjacent to an alkene group.

On this page
  • What is the Difference Between Enols Enolates and Enamines?
  • Comparative Table: Enols Enolates vs Enamines

    • Comparative Table: Enols Enolates vs Enamines

    Here is a table comparing the differences between enols, enolates, and enamines:

    Property Enols Enolates Enamines
    Definition Enols are alkenes with alcoholic functional groups. Enolates are the conjugate bases of enols. Enamines are alkenamines with amine groups attached to an alkene.
    Reactivity Enols are the least reactive among enols, enolates, and enamines. Enolates are more reactive than enols and enamines. Enamines have intermediate reactivity compared to enols and enolates.
    Preparation Enols are prepared by shifting a hydrogen atom from an alpha carbon to a carbonyl oxygen. Enolates are prepared by the deprotonation of enolizable ketones, aldehydes, and esters. Enamines are synthesized by condensation of an aldehyde or ketone with a secondary amine.
    Functional Group Enols contain a hydroxyl group attached to an alkene. Enolates contain a negatively charged oxygen atom as a functional group. Enamines contain an amine group attached to an alkene.
    Tautomerization Enols undergo tautomerization, usually seen as keto-enol interconversion. Enolates exhibit resonance of an extra electron between oxygen and carbon atoms. Enamines also undergo tautomerization, similar to enols.

    Enols, enolates, and enamines are three different types of organic compounds. Enols are formed by combining an alkene group with an alcohol group, enolates are derived from enols by removing a hydrogen atom from the hydroxyl group, and enamines are amine compounds with an amine group adjacent to a double bond.

    Read more:

    Guilherme Mazui

    Guilherme Mazui is graduated in journalism from the Federal University of Minas Gerais (UFMG) and a master's degree in Communication from the University of São Paulo (USP). In addition, he has experience in advertising writing and has worked as a content editor in several companies.