Editing Lithium diisopropylamide (section)

{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 450704638
| Name = Lithium diisopropylamide
| ImageFile = lithium diisopropylamide.png
| ImageSize = 150px
| ImageFile1 = File:Lithiumdiisopropylamid_v1.svg
| ImageSize1 = 
| ImageName = Lithium diisopropylamide
| PIN = Lithium ''N''-(propan-2-yl)propan-2-aminide
| OtherNames = LDA
|Section1={{Chembox Identifiers
| SMILES = [Li+].CC(C)[N-]C(C)C
| SMILES_Comment = ionic form
| SMILES1 = CC(C)N([Li])C(C)C
| SMILES1_Comment = covalent form
| SMILES2 = C1CCC[O+]1[Li-2]0[N+](C(C)C)(C(C)C)[Li-2]([O+]1CCCC1)[N+]0(C(C)C)C(C)C
| SMILES2_Comment = dimer with THF
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2006804
| InChI = 1/C6H14N.Li/c1-5(2)7-6(3)4;/h5-6H,1-4H3;/q-1;+1
| InChIKey = ZCSHNCUQKCANBX-UHFFFAOYAP
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H14N.Li/c1-5(2)7-6(3)4;/h5-6H,1-4H3;/q-1;+1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZCSHNCUQKCANBX-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 4111-54-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = OL028KIW1I
| RTECS =
| PubChem = 2724682
  }}
|Section2={{Chembox Properties
| Formula = {{chem2|LiN(CH(CH3)2)2}}
| MolarMass = 107.1233 g/mol
| Appearance = colourless solid
| Density = 0.79 g/cm<sup>3</sup>
| Solubility = Reacts with water
| MeltingPt = 
| BoilingPt = 
| pKa = 36 (THF)<ref>[http://evans.rc.fas.harvard.edu/pdf/evans_pKa_table.pdf Evans pKa Table]</ref>
| pKb = 
| Viscosity = 
  }}
|Section7={{Chembox Hazards
| ExternalSDS =
| MainHazards = corrosive
| FlashPt = 
}}
|Section8={{Chembox Related
| OtherAnions =
| OtherCations =
| OtherCompounds = [[Superbase]]s
  }}
}}

'''Lithium diisopropylamide''' (commonly abbreviated '''LDA''') is a [[chemical compound]] with the [[molecular formula]] {{chem2|LiN(CH(CH3)2)2}}. It is used as a strong [[base (chemistry)|base]] and has been widely utilized due to its good [[solubility]] in non-polar organic solvents and [[non-nucleophilic base|non-nucleophilic]] nature. It is a colorless solid, but is usually generated and observed only in solution. It was first prepared by Hamell and Levine in 1950 along with several other hindered lithium diorganylamides to effect the [[deprotonation]] of esters at the α position without attack of the carbonyl group.<ref>{{cite journal |language=en |title=Condensations Effected by the Alkali Amides. IV. The Reactions of Esters with Lithium Amide and Certain Substituted Lithium Amides1 |journal=The Journal of Organic Chemistry |volume=15 |pages=162–168 |year=1950 |last1=Hamell |first1=Matthew |last2=Levine |first2=Robert |doi=10.1021/jo01147a026}}</ref>