Which acid could not be prepared by treating a Grignard reagent with CO2? a. p-methylbenzoic acid.
b. cyclopentane carboxylic acid.
c. 4-oxopentanoic acid.
d. 3-methylbutanoic acid.

4-oxopentanoic acid.

Explanation:

In this case, we must remember that the Grignard reaction is a reaction in which carbanions are produced. Carboanions have the ability to react with CO2 to generate a new C-C bond and a carboxylate ion. Finally, the acid medium will protonate the carboxylate to produce the carboxylic acid group.

The molecules that can follow the mechanism described above are the molecules: p-methylbenzoic acid, cyclopentane carboxylic acid and 3-methylbutanoic acid. (See figure 1)

In the case of 4-oxopentanoic acid, the possible carbanion will attack the carbonyl group to generate a cyclic structure and an alcohol group (1-methylcyclopropan-1-ol). Therefore, this molecule cannot be produced by this reaction. (See figure 2)

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atomic mass = 39

number of neutrons = 20

number of protons= 19

electronic configuration = 1s2 2s2 2p6 3s2 3p6 4s1

the number of electron in first shell = 2

number of electrons in n=3 shell = 8