Part of OC-04 — Haloalkanes & Haloarenes

Mnemonics for Haloalkanes & Haloarenes

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Mnemonic 1: SN1 Conditions — "3 PAWs" SN1 needs: 3° substrate, Polar protic solvent, Atacks by Weak nucleophile, gives SN1 (Solo, one molecule in RDS). "A 3-Pawed cat SOLOs — Tertiary, Protic, And Weak nucleophile."

Mnemonic 2: SN2 Conditions — "1 SAP" SN2 needs: 1° substrate, Strong nucleophile, Aprotic solvent, Primary substrate. Rate = k[RX][Nu]. "1 SAP makes a backside attack — Primary, Strong, Aprotic, reacts with Precision."

Mnemonic 3: SN2 Stereochemistry — "Umbrella Flip" "SN2 = Umbrella — Backside attack flips the three groups like an umbrella inverting in wind = Walden Inversion." SN1 = Flat table (planar C+) → hit from both sides equally → Racemization. SN2 = Umbrella flip → one side attack only → Inversion.

Mnemonic 4: C-X Bond Order — "FiCkle BrI" Bond length (short to long): F → Cl → Br → I ("FiCkle BrI" = smallest F to largest I) Bond energy (strong to weak): F > Cl > Br > I (same order — shorter = stronger) Reactivity (SN2, slow to fast): RF → RCl → RBr → RI (weakest C-I breaks easiest)

Mnemonic 5: Named Reactions — "FINe SWAmP DOW"

  • FINkelstein = Iodide (NaI, IN acetone, drives by NaCl precipitate)
  • SWarts = F (AgF, SWapping Br for F, drives by AgBr precipitate)
  • DOW process = DOWn the barrel (extreme 623 K, 300 atm) to make phenol

Mnemonic 6: Saytzeff vs Hofmann — "MORE is Saytzeff, LESS is Hofmann (Bulky)"

  • Saytzeff = MORE substituted alkene (default, most reactions)
  • Hofmann = LESS substituted (only with BULKY base like t-BuO-) "Saytzeff Says MORE; Hofmann is Humble (LESS) — only when base is BULKy"

Mnemonic 7: Leaving Group Order — "I Broke, Couldn't Fight" I- > Br- > Cl- > F- as leaving groups I = best (I = "I left first"), F = worst (F = "F-ight to stay, won't leave") (Inverse of basicity: I- weakest base = best leaving group)

Mnemonic 8: Haloarene Reactivity — "RARE needs HEAT" Haloarenes are RAREly reactive: Resonance strengthens C-X, needs harsh conditions (HEAT = 623K, pressure = 300 atm). The Dow process is the "HEAT" that forces the reaction.

Mnemonic 9: Phosgene Hazard — "CHloroform in LIGHT → COCl2COCl_{2} = POIson" CHCl3CHCl_{3} + Light + O2O_{2}COCl2COCl_{2} (POIson gas). Store CHloroform in DArk bottles. "DARK protects from POIsonous transformation."

Mnemonic 10: DDT vs CFC — "DDT in FAT; CFCs in SKY" DDT stays in FAT tissue (lipophilic, bioaccumulates in fat, food chain magnification). CFCs go to the SKY (stratosphere, UV breaks C-Cl, Cl• destroys O3O_{3}). "DDT = FAT problem. CFCs = SKY problem."

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