Question

Vanillin

Sulfanilamide

Zolpidem

Raspberry

Proposed one synthetic route that would lead to a functional group or portion of

each molecule.

Propose an additional step that would transform each molecule (or a functional

group or portion of the molecule) into something else.

Answer 1

OH LOCH? CHC13 OCH3 LOCHz КОН Cro3 H2SO4 2-methoxyphenol CHO соон Reimer-Tiemann reaction Vanillin 4-hydroxy-3-methoxybenzoic acid 1) 2-methoxyphenol is converted to vanillin via Reimer-Tiemann reaction. Then the aldehyde group is oxidized with Cro3/H2SO4 to give 4-hydroxy-3-methoxybenzoic acid. CN HN NH2 1) NaNO2, HCI | 1 HCI HCI » || 1 2) Cu(CN)2, KCN O=S=0 O=S=0 O=S=O NH2 NH2 4-cyanobenzene-1-sulfonamide 2) Acetanilide like derivative is hydrolyzed to give Sulfanilamide, which is further diazotized to 4-cyanobenzene-1-sulfonamide.

الللللللللللللللللللللا H3C -CH3 H C DCC (dicyclohexyl carbodiimide) COOH --CH Сн o 1) KMnO4, H2O, Dimethylamine 2) Acidic workup 3) DCC coupling with dimethyl amine yields the zolpidem. That upon oxidation with KMnO4 gives benzylic position oxidation. Н.С -COOH N---CH3 H3C CH3 CHY CH3 H2, Rh/alumina NaBH4 EHO HO Raspberry Reduction of C=C gives Raspberry and further on reduction with NaBH4 gives alcohol. HO