Question

Draw structural formulas for the products of complete hydrolysis of meprobamate, phenobarbital, and pentobarbital in hot aqueous acid.

Short answer

Answer: The products of hydrolysis for each compound are as follows: a) Meprobamate: two molecules of 2-methyl-2-propylamine and one molecule of 3-propanedioic acid. b) Phenobarbital: 2,4,6-trioxohexanoic acid and 5-ethyl-5-phenyl-1,3-diazinan-2-ol. c) Pentobarbital: 2,4,6-trioxohexanoic acid, 5-ethyl-1,3-diazinan-2-ol, and 2-methyl-2-propylamine.

Step-by-step solution

Identify the structures of given compounds.

Meprobamate, phenobarbital, and pentobarbital are all drugs, and their structures can be found in a variety of sources such as textbooks, articles, or online databases. Draw their structures on paper or any drawing software.

Determine how each compound undergoes hydrolysis.

Hot aqueous acid will typically cause hydrolysis at ester or amide functional groups. Examine the structures of meprobamate, phenobarbital, and pentobarbital, and identify any ester or amide functional groups that will undergo hydrolysis. a) Meprobamate has two amide functional groups in its structure. b) Phenobarbital has one ester functional group. c) Pentobarbital has one ester and one amide functional groups in its structure.

Determine the products of hydrolysis for each compound.

When esters and amides are hydrolyzed, they typically break into the corresponding carboxylic acid and alcohol or amine components, respectively. a) Meprobamate hydrolysis: The two amide groups undergo hydrolysis, resulting in the formation of two molecules of corresponding amine (2-methyl-2-propylamine) and one molecule of the corresponding dicarboxylic acid (3-propanedioic acid). b) Phenobarbital hydrolysis: The ester group undergoes hydrolysis, resulting in the formation of the corresponding carboxylic acid (2,4,6-trioxohexanoic acid) and the corresponding alcohol (5-ethyl-5-phenyl-1,3-diazinan-2-ol). c) Pentobarbital hydrolysis: The ester and amide in pentobarbital undergo hydrolysis, resulting in the formation of the corresponding carboxylic acid (2,4,6-trioxohexanoic acid), the corresponding alcohol (5-ethyl-1,3-diazinan-2-ol), and the corresponding amine (2-methyl-2-propylamine).

Draw the structural formulas of the hydrolysis products.

Finally, draw the structural formulas of the hydrolysis products: a) Meprobamate hydrolysis products: 2-methyl-2-propylamine (you need to draw two molecules) and 3-propanedioic acid. b) Phenobarbital hydrolysis products: 2,4,6-trioxohexanoic acid and 5-ethyl-5-phenyl-1,3-diazinan-2-ol. c) Pentobarbital hydrolysis products: 2,4,6-trioxohexanoic acid, 5-ethyl-1,3-diazinan-2-ol, and 2-methyl-2-propylamine.