Lithium diisopropylamide (LDA) is used as a strong base in organic synthesis. LDA is itself prepared by an acid-base reaction between butyllithium and N, N-diisopropylamine, [ (CH3) 2CH]2NH. Write an equation for this reaction, and place the appropriate labels on each reagent and product from the following list: stronger acid, stronger base, weaker acid, weaker base.

Question

Chemistry

Bryson Heath

22 January, 13:13

Lithium diisopropylamide (LDA) is used as a strong base in organic synthesis. LDA is itself prepared by an acid-base reaction between butyllithium and N, N-diisopropylamine, [ (CH3) 2CH]2NH. Write an equation for this reaction, and place the appropriate labels on each reagent and product from the following list: stronger acid, stronger base, weaker acid, weaker base.

+4

Answers (1)

Know the Answer?

Bridget Ayala · Answer 1

Lithium diisopropylamide (LDA) is used in many organic synthesis and is a strong base. It is prepared by the acid base reaction of N, N-diisopropylamine ([ (CH₃) ₂CH]₂NH) and butyllithium (Li⁺⁻CH₂CH₂CH₂CH₃).

The equation is show below as:

[ (CH₃) ₂CH]₂NH + Li⁺⁻CH₂CH₂CH₂CH₃ ⇒ [ (CH₃) ₂CH]₂N⁻Li⁺ + CH₃CH₂CH₂CH₃

N, N-diisopropylamine ([ (CH₃) ₂CH]₂NH) is a weaker acid and hence, LDA ([ (CH₃) ₂CH]₂N⁻Li⁺) is stronger base. (Weaker acid has stronger conjugate base)

Butyllithium (Li⁺⁻CH₂CH₂CH₂CH₃) is a very strong base and hence, butane (CH₃CH₂CH₂CH₃) is a very weak acid. (Strong base has weaker conjugate acid)