4 nucleophiles that react with acid derivates
Primary amine
Ammonia
Alcohol
Water
What are the uses of acylation
- Cheaper
- Less corrosive
- Does not react w/ water as readily
- Safer as byproduct is Ethanoic acid not hcl
What affects the readiness of acylation
- magnitude of +charge on carbonyl carbon (depends on electron releasing/attracting power of the halogen group
- How easily the halogen is lost
- Strength of nucleophile
Why are acid chlorides more powerful than acid anhydrides
Cl has a greater charge and attracts more electrons density
What does the primary amine nucelophile produce
Amide
What does the ammonia nucleophile produce
N-substituted amide
What does the alcohol nucleophile produce
Ester
What does the water nucleophile produce
Carboxylic acid
Acylation
Process by which the acyl group is introduced into another molecule
Acid derivative
Contain acyl group as part of their structure
What’s an advantage of using propanoyl chloride over propanoic acid when preparing methyl propanoate from methanol?
Faster Not reversible Bigger yield Purer product No acid catalyst required
What’s an advantage of using propanoic anhydride instead of propanoyl chloride in the manufacture of methyl propanoate from methanol?
Anhydride less easily hydrolysed
Reaction is less exothermic
