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Behaviour of Biomolecules Lecture notes: Chemistry of the carboxyl group
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Behaviour of Biomolecules Lecture notes: Chemistry of the carboxyl group BSc Biomedical Sciences course

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  • November 7, 2023
  • 35
  • 2017/2018
  • Lecture notes
  • Ramon rios
  • Chemistry of the carboxyl group

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BIOL1021: Behaviour of Biomolecules
Dr. Ramon Rios: rrt1f11@soton.ac.uk




Behaviour of Biomolecules
1
Lecture 5: Chemistry of the carboxyl group

,REVISION LAST LECTURE
Consider reaction of an aldehyde/ketone with a secondary amine:

O R' R' R'
H N
+ N H + H2O
R catalyst R
R'
Enamine

via hemiaminal formation:

OH OH H
O H 1 OH 2 3

R R N R' R NR'2
R
H R'
R'2NH hemiaminal
then:
H
OH H 4
OH2
5 H
6

R R R NR'2 R NR'2 R NR'2
NR'2 NR'2
+ H2O
The iminium ion has no N-H bond so
• Identical to imine formation except in loss of H must take place from the
adjacent atom instead. 2
the final step.

, Chemistry of Imines
Mechanism: O R'
H N
+ R' NH2 + H2O
R R catalyst R R


First part (hemiaminal formation):


OH OH H
O H 1 OH 2 3
R R
R R R N R' R NR'
R R
H
H H
R'NH2 hemiaminal


1 Protonation of the C=O group on oxygen.
2 Nucleophilic attack by nitrogen lone-pair electrons from the 1 o amine.
3 Loss of a proton gives a hemiaminal intermediate.


Steps 1 3are slow below pH4 because the amine is protonated…
R'NH3 is not nucleophilic. 3
…and

, Compare hemiaminal formation…


OH OH H
O H OH
R R
R R R N R' R NR'
R R
H
H H
R'NH2 hemiaminal



…with hemiacetal formation:

H
O H OH OH
OH
R R
R R R O R' R
R R OR'
H
R'OH


Differ only in the identity of the nucleophile (amine or alcohol).


4

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