03/08/22

Title: What is Acylation?

1

Looking at the worksheet on

Acylation, read through the
introduction and example 1
Classroom and 2.
expectations

Arrive on time
Attempt Example 3 and 4.
Coat off

Bags off desks

Planner on
desk

Equipment on
desk
03/08/22
 Acylation = replacing an H with an
ACYLATION acyl group

O Acyl group from

O acyl chloride
R C
R C Cl
Acyl group
O O acid anhydride

R C O C R

© www.chemsheets.co.uk A2 1055 5-June-2016

 Acylation = replacing an H with an
ACYLATION acyl group

O O

R C Cl R' O H R C O R' HCl

© www.chemsheets.co.uk A2 1055 5-June-2016

 Acylation = replacing an H with an
ACYLATION acyl group

O H O H

R C Cl R' N H R C N R' HCl

H H
then +
HCl -
R' N H R' N H Cl

O H O H H
overall 2 R' + -
R C Cl N H R C N R' R' N H Cl

© www.chemsheets.co.uk A2 1055 5-June-2016

 Acylation = replacing an H with an
ACYLATION acyl group

e.g. ethanol + propanoyl chloride

O O

CH 3 CH 2 C Cl + HO CH2 CH3 CH3 CH2 C O CH2 CH3 + HCl

ethyl propanoate

e.g. methylamine + ethanoic anhydride

O O O O
-
CH3 C O C CH3 + 2 H 2N CH3 CH3 C NH CH3 + CH3 C O
N-methyl ethanamide +
H3N CH3

© www.chemsheets.co.uk A2 1055 5-June-2016

 Acylation = replacing an H with an
ACYLATION acyl group

e.g. water + propanoyl chloride

O O

CH 3 CH 2 C Cl + HO H CH3 CH2 C OH + HCl

propanoic acid

e.g. ammonia + ethanoyl chloride

O O
Cl
-
CH3 C Cl + 2 H 2N H CH3 C NH2 + +
NH
ethanamide 4

© www.chemsheets.co.uk A2 1055 5-June-2016

 Acylation = replacing an H with an
ACYLATION acyl group

e.g. propan-2-ol + ethanoyl chloride

O CH 3 O CH3

CH3 C Cl + HO CH CH3 CH3 C O CH CH3 + HCl

methylethyl ethanoate

e.g. ethylamine + propanoic anhydride

O O

CH3 CH2 C O C CH2 CH3 + 2 H 2N C H 2 C H 3

O O
-
CH3 CH2 C NH CH2 CH3 + CH3 CH2 C O
N-ethyl propanamide
+
H3N CH2 CH3

© www.chemsheets.co.uk A2 1055 5-June-2016

 Acylation = replacing an H with an
ACYLATION acyl group

e.g. propylamine + butanoyl chloride

O

CH 3 C H 2 C H 2 C Cl + 2 H 2N C H 2 CH 2 CH 3

O O
-
CH 3 C H 2 C H 2 C O CH 2 C H 2 C H 3 + CH 3 CH 2 CH 2 C O
propyl butanoate +
H3N C H 2 C H 2 CH 3

e.g. propan-1-ol + ethanoic anhydride

O O O O

CH 3 C O C CH 3 + HO CH 2 C H 2 CH 3 CH3 C O CH2 CH2 CH3 + CH3 C OH

propyl ethanoate

© www.chemsheets.co.uk A2 1055 5-June-2016

 Acylation = replacing an H with an
ACYLATION acyl group

e.g. water + butanoic anhydride

O O O
CH3 CH2 CH2 C O C CH2 CH2 CH3 + HO H 2 CH3 CH2 CH2 C OH
butanoic acid

e.g. ammonia + propanoic anhydride

O O

CH3 CH2 C O C C H 2 C H 3 + 2 H 2N H

O O
-
CH3 CH2 C NH2 + CH3 CH2 C O
propanamide +NH
4

© www.chemsheets.co.uk A2 1055 5-June-2016

ACYLATION Nucleophilic addition-elimination

alcohols & water

O
:O-

R C Cl R C Cl
+
O R
..
HO R
H

© www.chemsheets.co.uk A2 1055 5-June-2016

ACYLATION Nucleophilic addition-elimination

amines & ammonia

O
:O -

R C Cl R C Cl
+
H N R
..
H 2N R
H

then

H+ + RNH2 RNH3+
© www.chemsheets.co.uk A2 1055 5-June-2016
ACYLATION Nucleophilic addition-elimination

e.g. ethanol + propanoyl chloride

O
:O-

CH3 CH2 C Cl C H 3 CH 2 C Cl
+
O CH 2 C H 3
..
HO CH2 CH3
H

© www.chemsheets.co.uk A2 1055 5-June-2016

ACYLATION Nucleophilic addition-elimination

e.g. ammonia + ethanoyl chloride

O
:O -

CH 3 C Cl CH3 C Cl

H
+
N H then
.. H+ + NH3 NH4+
NH3
H

© www.chemsheets.co.uk A2 1055 5-June-2016

ACYLATION Nucleophilic addition-elimination

e.g water + propanoyl chloride

O
:O -

CH3 CH2 C Cl CH3 CH2 C Cl

+
O H
..
HO H H

© www.chemsheets.co.uk A2 1055 5-June-2016

ACYLATION Nucleophilic addition-elimination

e.g. propan-2-ol + ethanoyl chloride

O
:O-

CH3 C Cl CH3 C Cl
+
O CH CH3
..
HO CH CH3 H CH3
CH3

© www.chemsheets.co.uk A2 1055 5-June-2016

ACYLATION Nucleophilic addition-elimination

e.g. propylamine + butanoyl chloride

O
:O -

C H 3 CH 2 C H 2 C Cl CH3 CH2 CH2 C Cl

H
+
N C H 2 C H 2 CH 3
..
H 2N C H 2 C H 2 C H 3 H

then
+
H+ + H 2N C H 2 CH 2 CH 3 H3N CH 2 C H 2 C H 3

© www.chemsheets.co.uk A2 1055 5-June-2016