1. alcohols
p799 (special)
p798 (special)**
Amide
Carboxylic acid
p814
p795-6 acid and base
p794-5
p803
- need to work out
p802
p810 acid and base
Acid chloride
p795 – need to work out
p807 – need to work out
Ester
Acid anhydride

2. Chapter 21 – addition then R drops off - substitution
1. R- is halide – Acid Halides
2. R – is RCOO – Acid anhydride (same as 1)
3. R- is RO - ester
4. R- is RNH – amide (same as 3)
5. R- is OH – carboxylic acid
Increasingly unreactive

3. Chapter 21 – addition then R drops off - substitution
1. R- is halide – Acid Halides
Nu is H2O - Hydrolysis of Acid halides (21.4 p.802 – top)
Nu is ROH – Esterification/alcoholysis (p 802 – bottom)
Nu is RCOOH – Acid anhydride (p 802 middle)
Nu is amine - amide/amminolysis (p 803)

4. Chapter 21 – addition then R drops off - substitution
2. R- is carboxylate – Acid anhydride (mechanism exactly same as acid chloride) – carboxylate not so good leaving group so
Slightly less reactive.
Nu is H2O - Hydrolysis of Acid anhydride (p 806 bottom)
Nu is ROH – Esterification/alcoholysis (p 807 – top)
Nu is amine - amide/amminolysis (p middle)
Classwork:

5. Chapter 21 – addition then R drops off - substitution
R- is alkoxide – Ester
alkoxide not so good leaving group so must be catalysed by
acid or base
Slightly less reactive.
Nu is H2O - Hydrolysis of ester
base (Fig 21.7) / acid (Fig 21.8)
Nu is ROH – trans esterification/alcoholysis
Nu is amine - amide/amminolysis
Classwork: 21.43

6. Chapter 21 – addition then R drops off - substitution
R- is amine – amide
amine not so good leaving group so must be catalysed by
acid or base
Slightly less reactive – exactly same mechanism as ester
Nu is H2O - Hydrolysis of ester / acid (p 814)

7. Chapter 21 – addition then R drops off - substitution
R- is OH – Carboxylic acid
OH very bad leaving group so must be converted into
a good leaving group by reacting with some reagent
Nu is ROH - Esterification / acid catalysed (Fig 21.4)
Nu is “amine” – induction with DCC (Fig 21.5)
Nu is ‘halide” - SOCl2 (p 795 top)
Classwork: 21.36(h); 21.41

8. Chapter 21 – addition then R drops off - substitution
Other types of nucleophiles (not covered in this module)
“hydride ion” - reduction with LiAlH or NaBH4
Grignard reagent and other organometallics
Homework: 21.44, 21.48, 21.52