How are the following conversions carried out (a)phenol to picric acid (b) phenol to anisole (c)propene to propan 1 ol
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Methods to carry out the specified chemical conversions mentioned below:
(a) Phenol to Picric Acid
: Phenol (C6H5OH) is converted to picric acid (2,4,6-trinitrophenol) through nitration.
Treat phenol with a mixture of concentrated nitric acid (HNO3) and concentrated sulfuric acid (H2SO4) at 60–80C. Sulfuric acid protonates nitric acid to form nitronium ions (NO2 +), which attack the aromatic ring. Initially, phenol forms o-nitrophenol and p-nitrophenol. Further nitration under controlled heating introduces two more nitro groups, yielding 2,4,6-trinitrophenol (picric acid). Cool the mixture, filter, and recrystallize to isolate the yellow crystalline product.
(b) Phenol to Anisole
: Phenol is converted to anisole (C6H5OCH3) via Williamson’s ether synthesis.
React phenol with a strong base like sodium hydroxide (NaOH) to form sodium phenoxide (C6H5ONa). Then, treat sodium phenoxide with methyl iodide (CH3I) or dimethyl sulfate in an aprotic solvent like acetone at room temperature. The methoxide group attaches to the phenyl ring, forming anisole. Distill the product to purify it.
(c) Propene to Propan-1-ol
: Propene (CH3CH=CH2) is converted to propan-1-ol (CH3CH2CH2OH) via hydroboration-oxidation.
First, react propene with borane (BH3) in tetrahydrofuran (THF) to form trialkylborane. Then, oxidize it with hydrogen peroxide (H2O2) and sodium hydroxide (NaOH) at 0–10 degree Celsius. This anti-Markovnikov addition introduces a hydroxyl group to the less substituted carbon, yielding propan-1-ol. Purify by distillation.
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