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{{Short description|
[[Image:Lactams General Formulae V.1.png|thumb|right|450px|From left to right, the above are general structures of
A '''lactam''' is a [[Cyclic compound|cyclic]] [[amide]], formally derived from an [[amino]] [[alkanoic acid]] through [[cyclization]] reactions. The term is a [[portmanteau]] of the words ''[[lactone]]'' + ''[[amide]]''.
==Nomenclature==
[[Greek_alphabet#Letters|Greek
{| {{table}}
! Ring size<br />(number of atoms in the ring)
* [[β-Lactam]] (4-atom rings)▼
! {{nobr|[[Systematic name]]}}
! [[IUPAC name]]
! {{nobr|[[Trivial name|Common name]]}}(s)
! Structure
|-
|3
|[[α-Lactam]]
|Aziridin-2-one
|α-Acetolactam
|[[File:Α-Lactam structure.svg|thumb|100px]]
|-
|4
|Azetidin-2-one
|β-Propiolactam
|[[File:Beta-lactam.svg|thumb|100px]]
|-
|5
|[[γ-Lactam]]
|Pyrrolidin-2-one
|{{ubl|γ-Butyrolactam|2-Pyrrolidone}}
|[[File:Structural formula of 2-pyrrolidone.svg|thumb|100px]]
|-
|6
|[[δ-Lactam]]
|Piperidin-2-one
|{{ubl|δ-Valerolactam|2-Piperidinone|2-piperidone}}
|[[File:2-piperidinone.svg|thumb|100px]]
|-
|7
|[[ε-Lactam]]
|Azepan-2-one
|{{ubl|ε-Caprolactam|Caprolactam}}
|[[File:Caprolactam-2D-skeletal.png|thumb|100px]]
|}
This ring-size nomenclature stems from the fact that
==Synthesis==<!-- This section is linked from [[Organic reaction]] -->
General synthetic methods
===Beckmann rearrangement===
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===Schmidt reaction===
Lactams form from [[cyclic ketones]] and [[hydrazoic acid]] in the [[Schmidt reaction]]. Cyclohexanone with hydrazoic acid, forms [[Caprolactam|ε - Caprolactum]], which upon treatment with excess acid forms [[Pentylenetetrazol|Cardiazole]], a heart stimulant.
===Cyclization of amino acids===
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:[[File:Preparation_of_gamma_and_beta_lactams.svg|400px|Preparation of VL and beta lactam]]
==Lactam–lactim tautomerism==
A '''lactim''' is a cyclic [[
:[[File:Lactam-Lactim-Tautomerie.svg|thumb|320px| Lactam Lactim]]
==Reactions==<!-- This section is linked from [[Organic reaction]] -->
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==References==
{{Reflist}}
==External links==
*{{
{{Authority control}}
[[Category:Functional groups]]
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