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why is  Lithium diisopropylamide soluble in non polar solvents?

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kausik911 | Student, Undergraduate | (Level 1) Honors

Posted April 26, 2013 at 7:35 PM via web

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why is 

Lithium diisopropylamide soluble in non polar solvents?

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llltkl | College Teacher | (Level 3) Valedictorian

Posted April 27, 2013 at 3:29 PM (Answer #1)

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Lithium diisopropylamide is a chemical compound with the formula [(CH3)2CH]2NLi. In its structural formula there are two large non-polar isopropyl groups attached to the nitrogen atom and a very small ionic part in the form of N-Li+. However, it forms a dimeric structure through the lithium atoms. As a consequence the polar portion becomes masked further with large alkyl parts dominating in its structure, rendering it soluble in non-polar and weakly polar solvents, thereby expanding its applicability in organic syntheses. Generally abbreviated LDA, it is a strong base used in organic chemistry for the deprotonation of weakly acidic compounds.

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