Question

Which is the stronger base among $ NaOEt $ (sodium acetate) and $ LDA $ (lithium diisopropylamide)?

Answer 1

Hint :We know that the base refers to a substance which in water solution tends to be slippery to the touch, bitter in taste and changes the colour of indicators (i.e. turns the red litmus paper to blue). Base reacts with the acids in order to form salts.

Complete Step By Step Answer:
To solve this problem firstly we should know what bases are and how they are classified into strong and weak bases. A strong base refers to a base that completely dissociates in an aqueous solution. Strong bases ionize in water and yield one or more hydroxide ions per molecule of the base. In chemistry, bases are substances that release hydroxide ions, have slippery nature, they have a bitter taste, and can change the colour of indicators, react with acids to form salts and can promote chemical reactions. We can differentiate bases as the opposite of Acids; however some acids may also act as bases. We can classify bases into four types which are known as
Strong base: It is a compound that has an ability to remove a proton from a very weak acid. Or they completely dissociate into its ions when in water. Examples are potassium hydroxide $ \left( KOH \right), $ sodium hydroxide $ \left( NaOH \right). $
Weak base: When there is dissociation in water. The solution contains both the weak base as well as strong acid.
Neutral base: When a bond is formed with a neutral acid that shares an electron pair.
Solid base: They are active in the solid form. Examples are silicon dioxide and sodium hydroxide mounted on alumina.
The basic nature of the species is inversely proportional to the stability of the species ion. Let us discuss each one of the bases given $ NaOEt $ and $ LDA. $ $ NaOAc $ is not a strong base as the negative charge can be delocalized among the two oxygen’s. In order to compare whether $ LDA $ or $ NaOEt $ is more basic, we can consider two reactions:
Ethanol $ + $ $ LDA. $
Sodium ethoxide $ + $ diisopropylamine (conjugate acid of $ LDA $ ).
The first reaction proceeds much further than the second one. LDA can only be formed from treatment of diisopropylamine with n-butyllithium, which is much more basic than sodium ethoxide. From this, we conclude that LDA is more basic than sodium ethoxide. Thus, the decreasing basicity: $ LDA\text{ }>\text{ }NaOEt\text{ }>\text{ }NaOAc $

Note :
Remember that the base strength of any species is its capability to accept from another species. Greater the ability of any species to accept from another species, the greater is its base strength. There are certain other measurements for finding out the basic strength of bases such as its electron donating capacity.