Question

Show how the following compounds can be synthesized. The only carbon-containing compounds available to you for each synthesis are shown.

Short answer

Aldol addition constitutes a reaction between two molecules of aldehyde or two molecules of the ketone.When the reactant is an aldehyde, the product becomes a -hydroxyaldehyde.

Step-by-step solution

Aldol addition reaction

Aldol addition constitutes a reaction between two molecules of aldehyde or two molecules of the ketone.When the reactant is an aldehyde, the product becomes a -hydroxyaldehyde.

Showing how the given compound can be synthesized

a. In this reaction, propan-1-ol reacts with NaOCl and acetic acid to form propionaldehyde. This further reacts with a base and water to form 3-hydroxy-2-methylpentanal.

This reacts with HCl and heat to form (E)-2-methylpent-2-enal. This further reacts with hydrogen and raney nickel to form 2-methylpentan-1-ol. The reaction is given below.

b. In this reaction, propan-2-ol reacts with NaOCl and acetic acid to form propan-2-one. This further reacts with a base and water to form 4-hydroxy-4-methylpentan-2-one. This reacts with and to form 2-methylpentan-2,4-diol.

This reacts with sulfuric acid and heat to form 4-methylpenta-1,3-diene. This reacts with and Pd/C to form 2-methylpentane.

c. In this reaction, ethanol reacts with NaOCl and acetic acid to form acetaldehyde. This further reacts with a base and water to form 3-hydroxybutanal. This reacts with and to form butan-1,3-diol.

This reacts with HCl and propan-2-one to form 2,2,4-trimethyl-1,3-dioxane. The reaction can be given as: