Alcohols: Multi-Step Synthesis
Suggest a synthetic scheme for the conversion shown on the left using the starting materials shown below. Work each problem backwards, and draw the structures of the intermediates required for the conversion, and the reaction conditions necessary for each step.Click the mouse on the buttons to view the synthetic logic for each step, the structures of the intermediates and the solution to the problem;
click here to view the potential starting materials.
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Working backwards, this molecule is a brominated benzyl alcohol. The two substituents are meta to each other and, among the starting materials, there is only one aromatic compound that contains a meat-directing group; benzaldehyde. To make this molecule, we must first brominate benzaldehyde and then reduce the carbonyl to the alcohol.
Working backwards, this molecule is a brominated benzyl alcohol. The two substituents are meta to each other and, among the starting materials, there is only one aromatic compound that contains a meat-directing group; benzaldehyde. To make this molecule, we must first brominate benzaldehyde and then reduce the carbonyl to the alcohol. Next, suggest a synthesis of 3-bromobenzaldehyde, beginning with benzaldehyde.
Benzaldehyde is first brominated by reaction with Br2 in the presence of FeCl3. In a second step, m-bromobenzaldehyde is reduced using borohydride to give the final product.