Acylation
The amine displaces chloride from the carbonyl, giving the amide. Below it: runs of this reaction that somebody published, with the conditions they used.
What it needs, and what it gives
- Reaction class
- Acylation
- Cold, often with a base to take up the hydrogen chloride.
- balanced — the co-products are written out, not dropped
- Mechanism
- Nucleophilic acyl substitution, 3 steps
- Acyl chlorides react violently with water.
These notes are flags, not a risk assessment. Read the primary source and your own institution's rules before working at the bench.
How it is thought to work
The nucleophile adds to the carbonyl, the carbon holds four groups for a moment, and the leaving group is pushed out as the double bond comes back.
- The nucleophile attacks the carbonyl carbon
- The carbonyl comes back and the leaving group goes
- A base takes the proton
Related transformations the engine performs
Worked examples
Reading these records
Everything on a record page came from the source that published it. Conditions the source did not state are shown as not recorded, and no typical value is substituted for them. Yields are whatever was measured by whoever ran the experiment.
Other classes
Buchwald–Hartwig amination
Recorded reactions with their conditions, and worked examples where a procedure and atom map were published.
Suzuki–Miyaura coupling
Recorded reactions with their conditions, and worked examples where a procedure and atom map were published.
Reduction
Recorded reactions with their conditions, and worked examples where a procedure and atom map were published.
Deprotection
Recorded reactions with their conditions, and worked examples where a procedure and atom map were published.
Reductive amination
Recorded reactions with their conditions, and worked examples where a procedure and atom map were published.
Oxidation
Recorded reactions with their conditions, and worked examples where a procedure and atom map were published.