Question

Draw the structure of the organic product formed when the following compounds undergo the three-step reaction sequence indicated. Highlight, by using "graded select" tool and clicking on, the carbon atoms in the product that come fromt he diethyl malonate.

Answer 1

Concepts and reason

The concept used to solve this problem is, malonic ester forms the substituted acetic acid.

The diethyl malonate is reacted with strong base followed the nucleophilic substitution with the unhindered alkyl halide, tosylate or electrophilic reagent forms alkylated malonic ester, which is hydrolyzed and allowed to decarboxylate.

Fundamentals

Unhindered alkyl halides must be used in the malonic ester synthesis.

The reaction is as follows:

The reaction is as follows:

The reaction is as follows:

Ans:

The structure of the organic product with the highlighted (red colored) carbon atoms that comes from diethyl malonate is as follows:

Answer 2

Concepts and reason

The concept used to solve this problem is, malonic ester forms the substituted acetic acid.

The diethyl malonate is reacted with strong base followed the nucleophilic substitution with the unhindered alkyl halide, tosylate or electrophilic reagent forms alkylated malonic ester, which is hydrolyzed and allowed to decarboxylate.

Fundamentals

Unhindered alkyl halides must be used in the malonic ester synthesis.

The reaction is as follows:

The reaction is as follows:

The reaction is as follows:

Ans:

The structure of the organic product with the highlighted (red colored) carbon atoms that comes from diethyl malonate is as follows: