Q37P - Organic Chemistry (Mcmurry)

Question

Arrange the compounds in each of the following sets in order of increasing basicity:

(a) Magnesium acetate, magnesium hydroxide, methyl magnesium bromide

(b) Sodium benzoate, sodium p-nitrobenzoate, sodium acetylide

(c) Lithium hydroxide, lithium ethoxide, lithium formate

Step-by-Step Solution

Answer

The order of the compounds in respect to increasing basicity can be found for the following sets.

Step 1: Increasing the order of their basicity among Magnesium acetate, magnesium hydroxide, methylmagnesium bromide

The derivation of three acids for these compounds are water, acetic acid and methane. The increasing order of acidity are acetic acid>water>acidity. The basicity of the bases are in the reverse order as, 

Magnesium Acetate > Magnesium Hydroxide > Methylmagnesium Bromide.

The increasing order of basicity are 

Magnesium Acetate < Magnesium Hydroxide < Methylmagnesium Bromide.

Step 2: Increasing the order of their basicity among Lithium hydroxide, lithium ethoxide, lithium formate

The derivation of three acids for these compounds are water, ethanol and formic acid. The increasing order of acidity are formic acid>water>ethanol. The basicity of the bases are in the reverse order as,

Lithium Formate < Lithium Hydroxide < Lithium Ethoxide.

The increasing order of basicity are 

Lithium Formate < Lithium Hydroxide < Lithium Ethoxide.