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Behaviour of biomolecules Lecture notes: Imines, Acids and Bases
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BSc Biomedical Sciences course at the University of Southampton Behaviour of biomolecules Lecture notes: Imines, Acids and Bases
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BIOL1021: Behaviour of BiomoleculesDr. Ramon Rios: rrt1f11@soton.ac.uk
Behaviour of Biomolecules
1
Lecture 4: Imines and Acid&Base
, Chemistry of Acetals
1. Introduction to Carbonyl Group Chemistry:
• The C=O bond is referred to as the carbonyl group so the following are all
termed carbonyl compounds:
O O O O O
R' R'
R R R H R OH R O R N
H
Ketone Aldehyde Carboxylic Carboxylic Amide
acid ester
-
• Oxygen is more electronegative than O O O
+ and
carbon so the C=O bond is polarised:
• Hence carbonyl compounds typically undergo:
O O H
O OH OH
Nuc
Nuc
Attack by nucleophiles at the electron- Reaction with electrophiles (including H 2
) at
deficient carbon atom the electron-rich oxygen atom
, Chemistry of Acetals
Mechanism:
O H R' O O R'
+ 2 R'OH + H2O
R R catalyst R R
• The mechanism involves 7 steps and takes place via a hemiacetal intermediate.
First part (hemiacetal formation):
H
O H OH OH
1 OH 2 3
R R
R R R O R' R
R R OR'
H
R'OH
1
Protonation of the C=O group on oxygen.
2 Nucleophilic attack by oxygen lone-pair electrons from the alcohol (1 st
molar eq.).
3 Loss of a proton gives a hemiacetal intermediate. 3
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