Further Synthetic Routes (OCR A-Level Chemistry A): Flashcards

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Further Synthetic Routes
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Reagent for chain extension via nitrile formation

\ceNaCN\ce{NaCN} in ethanol

Oxidise 1° alcohol to carboxylic acid: reagent + conditions

\ceK2Cr2O7/H2SO4\ce{K2Cr2O7/H2SO4}, reflux

Convert carboxylic acid to acyl chloride: reagent

\ceSOCl2\ce{SOCl2} (thionyl chloride)

Reduce nitrobenzene to aniline: reagent

\ceSn\ce{Sn} and conc. \ceHCl\ce{HCl}

Aniline + \ceBr2(aq)\ce{Br2(aq)}: catalyst needed?

No catalyst needed (activated ring)

Phenol + \ceBr2(aq)\ce{Br2(aq)} at room temp: product

2,4,6-tribromophenol (white ppt)

Best approach for planning synthesis routes

Retrosynthetic analysis (work backwards)

\ce−NO2\ce{-NO2} group directing effect on benzene

Meta-directing (positions 3,5)

\ce−NH2\ce{-NH2} and \ce−OH\ce{-OH} groups: directing effect

2,4-directing

Nitrile + \ceH2O/HCl\ce{H2O/HCl}: product (chain extended)

Carboxylic acid

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