NUCLEOPHILES

• WHAT MUST NUCLEOPHILES HAVE?

  lone pair of electrons to attack slightly positive carbonyl carbon
• WHAT ARE THE BEST NUCLEOPHILES?

  best electron donors
• EXAMPLES OF NUCLEOPHILES (DECREASING REACTIVITY)?

  primary amine > ammonia > alcohol > water
• WHEN REACTED WITH ACID DERIVATIVES WHAT DO PRIMARY AMINES FORM?

  N-substituted amides
• WHEN REACTED WITH ACID DERIVATIVES WHAT DOES AMMONIA FORM?

  amides
• WHEN REACTED WITH ACID DERIVATIVES WHAT DO ALCOHOLS FORM?

  esters
• WHEN REACTED WITH ACID DERIVATIVES WHAT DOES WATER FORM?

  carboxylic acids
• WHY ARE PRIMARY AMINES MORE REACTIVE THAN AMMONIA?

  • R group gives electrons to N
  • lone pair more readily available
• WHY ARE ALCOHOLS LESS REACTIVE THAN AMMONIA?

  • O more electronegative than N
  • harder to donate electron pair
• WHY IS WATER LESS REACTIVE THAN ALCOHOL?

  • R group gives electrons to O
  • lone pair more readily available
• WHAT DO ALL THESE NUCLEOPHILES REACT WITH ACYL CHLORIDES/ ACID ANHYDRIDES IN?

  nucleophilic addition-elimination reactions

  -> give off misty HCl fumes

  -> occur at room temperature

  -> all nucleophiles are neutral and must lose a H+ in reaction