Organic Reaction Pathways Worksheet ((better)) Jun 2026

A worksheet forces you to ask: “What reagent goes over this arrow?” and “What type of reaction is this (SN1, SN2, E1, E2)?” This active recall is ten times more effective than passive reading.

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Benzene → Nitrobenzene (HNO₃/H₂SO₄) → Phenylamine (Sn + conc. HCl) A worksheet forces you to ask: “What reagent

Mastering Chemistry: A Comprehensive Guide to Organic Reaction Pathways HCl) Mastering Chemistry: A Comprehensive Guide to Organic

| Transformation | Reagents/Conditions | Reaction Type | Mechanism Clue | | :--- | :--- | :--- | :--- | | Alkene → Alkane | H2, Pt/Pd/Ni (Catalytic hydrogenation) | Reduction (Addition) | Syn addition | | Alkene → Alcohol (Markovnikov) | H2O, H2SO4 (acid-catalyzed hydration) | Electrophilic addition | Carbocation intermediate | | Alkene → Alcohol (Anti-Markovnikov) | 1. BH3·THF 2. H2O2, OH– | Hydroboration-oxidation | Syn addition, no rearrangement | | Alkene → Dihalide | Br2 (or Cl2) in CCl4 | Halogenation | Anti addition via bromonium ion | | Alkene → Halohydrin | Br2, H2O | Halohydrin formation | Regioselective (OH to more sub. C) | | Alkene → Epoxide | m-CPBA (peroxyacid) | Epoxidation | Concerted, stereospecific | | Alkene → Diol (syn) | OsO4 or KMnO4 (cold, dilute) | Dihydroxylation | Syn addition | | Alkene → Diol (anti) | 1. RCO3H 2. H3O+ | Epoxide ring opening | Anti addition | | Alkene → Alkyl halide | HX (HCl, HBr, HI) | Hydrohalogenation | Markovnikov; rearrangements possible | | Alkene → Aldehyde (ozonolysis) | 1. O3 2. DMS | Oxidative cleavage | Breaks C=C into C=O |