Interactions | Reactions | Processes

Classified as: Substitution: Nucleophilic @ Acyl-Nfg

Many acyl functions (for example acid chlorides, R-COCl, and to a lesser extent esters, R-COOR) are highly susceptible to attack by nucleophiles. According to resonance theory, the adjacent carbonyl function stabilises the reaction transition state by delocalising any net negative charge onto the oxygen.

An alternative view is that the oxygen polarises the adjacent carbon (with respect to the sp3 analog) which increases susceptibility to Nu attack.

Confusingly, this sequence is also known as the "tetrahedral" mechanism and as "addition-followed-by-elimination".

For more information look in the Chemogenesis webbook sections on substitution reactions and substitution, transfer, abstraction, displacement (STAD).

(CH3CO)2CO
  +  
2
[OH]–
         
2
[CH3COO]–
  +  
H2O

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(CH3CO)2CO
  +  
2
R–OH
  +  
         
CH3COOR
  +  
CH3COOH

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(CH3CO)2CO
  +  
NH3
         
CH3CONH2
  +  
CH3COOH

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RCOCl
  +  
H2O
         
RCOOH
  +  
HCl

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RCOCl
  +  
R–OH
  +  
         
  +  

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RCOCl
  +  
2
NH3
         
  +  
NH4Cl

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RCOCl
  +  
Li[Al(OtBu)3H]
1.0M in THF
  +  
         
RCHO

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RCOCl
  +  
H2
  +  
Pd
on BaSO4
         
RCHO
  +  
HCl

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RCOCl
  +  
R2CuLi
  +  
         

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RCOOH
  +  
R–OH
         
  +  
H2O

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  +  
[OH]–
         
RCOO–
  +  
NH3

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  +  
R–NH2
         
  +  
R–OH

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RCOCl
  +  
RCOO–
         
(RCOO)2O
  +  
Cl–

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  +  
[OH]–
         
RCOO–
  +  
R–OH

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  +  
NH3
         
  +  
R–OH

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  +  
LiAlH4
         
RCH2OH
  +  
R–OH

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  +  
         
RCHO
  +  
R–OH

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  +  
RMgX
         
R3COH

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  +  
  +  
R–OH
         
  +  
RO–

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2
  +  
CH3CH2O–
  +  
CH3CH2OH
         
  +  
CH3CH2O–

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RCOCl
  +  
         
  +  
Cl–

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RCOCl
  +  
[SCN]–
         

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  +  
RO–
         

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CH3COOH
  +  
CH3CH2OH
  +  
H+
         
  +  
H2O

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  +  
H2O
  +  
H+(aq)
         
  +  
RCOOH

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  +  
2
NaOH
  +  
OH–(aq)
         
  +  
RCOO–
  +  
2
Na+

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  +  
NaOH
  +  
OH–(aq)
         
RCOO–
  +  
CH3OH

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CH3COOR
  +  
  +  
Base–
Proton abstractor
         

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  +  
(CH3CO)2CO
         
  +  
CH3COOH

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  +  
         
  +  
CH3OH

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  +  
2
(CH3CO)2CO
         
  +  
2
CH3COOH

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  +  
(CH3CO)2CO
         
  +  
CH3COOH

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  +  
2
NH3
         
  +  
2
HCl

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RCOCl
  +  
H2S
         
  +  
HCl

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  +  
(CH3)2NH
         
  +  
CH3OH

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1000
  +  
1000
         
Terylene
  +  
2000
H2O

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  +  
NH3
         
HCONH2
  +  
CH3OH

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2
HCONH2
  +  
H2SO4
  +  
2
H2O
         
2
HCOOH
  +  
(NH4)2SO4

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  +  
CH3NH2
         
  +  
CH3OH

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  +  
CH3OH
  +  
H+
         
  +  
H2O

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Peanut
Oil
  +  
H2O
  +  
NaOH(aq)
         
  +  
Oleic Acid
  +  
Linoleic
Acid
  +  
CH3(CH2)14COOH

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CH3COCl
  +  
NH3
         
CH3CONH2
  +  
HCl

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(CH3CO)2CO
  +  
H2O
         
2
CH3COOH

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CH3COCl
  +  
H2O
         
CH3COOH
  +  
HCl

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CH3COCl
  +  
2
CH3CH2NH2
         
  +  
[CH3CH2NH3]+
  +  
Cl–

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  +  
(CH3CO)2CO
         
  +  
CH3COOH

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CH3COCl
  +  
2
NH3
         
CH3CONH2
  +  
NH4Cl

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  +  
CH3COCl
         
  +  
HCl

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  +  
CH3CH2OH
         
  +  
HCl

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  +  
CH3OH
  +  
H2SO4
         
  +  
H2O

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CH3CH2COOH
  +  
  +  
H2SO4
         
  +  
H2O

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  +  
  +  
H+
         
  +  
H2O

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  +  
[OH]–
  +  
H2O
         
  +  

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  +  
NaOH(aq)
         
CH3COONa
  +  
CH3CH2OH

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  +  
H2O
         
  +  
HCl

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  +  
2
NH3
         
  +  
NH4Cl

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  +  
         
  +  
HCl

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  +  
H2O
         
2

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  +  
NH3
         
  +  
  +  
[NH4]+

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  +  
         
  +  

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(CH3CO)2CO
  +  
2
CH3NH2
         
  +  
[CH3NH3]+
  +  
[CH3COO]–

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CH3COCl
  +  
2
CH3NH2
         
  +  
[CH3NH3]+
  +  
Cl–

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2
  +  
CH3COCl
         
  +  
  +  
Cl–

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  +  
H2O
         
CH3COOH
  +  
CH3OH

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© Mark R. Leach 1999 –

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