Flashcards · 9701 · A Level Topic 36

Organic synthesis (A Level) flashcards

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Reactions that add carbon atoms (A Level): KCN in ethanol with a halogenoalkane (nitrile); HCN with an aldehyde or ketone (hydroxynitrile); Friedel–Crafts alkylation or acylation of an arene.
What do NaBH₄, LiAlH₄ and H₂/Ni each reduce?: NaBH₄: aldehydes and ketones only. LiAlH₄: also carboxylic acids, esters, nitriles and amides (not isolated C=C). H₂/Ni: alkenes, the benzene ring and nitriles (not acids, esters, amides).
Route: methylbenzene → benzamide: 1 Hot alkaline KMnO₄, then dilute acid → benzoic acid. 2 SOCl₂ (or PCl₅) → benzoyl chloride. 3 Excess NH₃, room temperature → benzamide (by-product NH₄Cl).
Route: benzene → phenol: 1 Conc. HNO₃/conc. H₂SO₄ → nitrobenzene. 2 Sn/conc. HCl, then NaOH → phenylamine. 3 NaNO₂/dilute HCl below 10 °C → diazonium salt. 4 Warm with water → phenol.
Three questions to ask at each step of a synthesis: Does the carbon skeleton change? What is the oxidation level (distil or reflux)? Are the conditions compatible with groups already present?