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Potassium cyanide (KCN) dissolved in ethanol/water mixture. The Product: Nitrile (alkanenitrile). The Mechanism: Nucleophilic substitution (typically SN2).

| Factor | Favors Substitution (SN2 or SN1) | Favors Elimination (E2 or E1) | |---|---|---| | | Lower temp (25°C) | Higher temp (>60°C, reflux) | | Nucleophile/Base | Strong nucleophile, weak bulky base (e.g., OH⁻, CN⁻, NH₃) | Strong, bulky base (e.g., KOH in ethanol , not water; or tert-butoxide) | | Halogenoalkane structure | Primary (SN2 only); Tertiary (SN1) | Tertiary (E1 or E2); primary needs strong bulky base (E2) | | Solvent | Polar protic (water, alcohols) for SN1; Polar aprotic (DMSO, acetone) for SN2 | Polar protic also works; non-polar favors E2 |

Both reactions start with the same halogenoalkane and a base/nucleophile (e.g., OH⁻). The outcome depends on:

“1-bromopropane is heated with NaOH(aq) and separately with NaOH in ethanol. State the major product in each case and explain.”