FACTORS

• FACTORS AFFECTING ACYLATION SPEED?

  • magnitude of slightly positive charge on carbonyl carbon
  • how easily Z is lost
  • how good nucleophile is
• WHAT DOES THE MAGNITUDE OF THE SLIGHTLY POSITIVE CHARGE ON CARBONYL CARBON DEPEND ON?

  electron-releasing/ attracting power of Z
• WHAT IS Z?

  leaving group
• WHAT ARE GOOD LEAVING GROUPS?

  groups that strongly attract electrons, as they tend to form stable negative ions (Z-)
• WHAT ARE MORE REACTIVE ACID CHLORIDES OR ACID ANHYDRIDES?

  acid chlorides
• WHAT ARE GOOD ACYLATING AGENTS?

  acyl chlorides and acid anhydrides
• WHY ARE ACYL CHLORIDES AND ACID ANHYDRIDES GOOD ACYLATING AGENTS?

  • Z groups withdraw electrons from carbonyl carbons
  • make carbon more positive and therefore more reactive to nucleophiles