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Chem 343 – Organic Reactions Chapter 10 Prepared by José Laboy, MS http://www.chem.wisc.edu/areas/clc (Resource page) Reactions of Alcohols #8: Reaction of a 1° Alcohol with Hydrogen Halides NaBr / H2SO 4 OH Mechanism Br Br O OH O S H2O OH OH2 Br H O S N2 Reaction Sometimes the reagent is shown as HBr, etc. Works well with NaCl / H2SO4 and NaBr / H2SO4. There’s always the alkene by an E2 mechanism. Ether formation is also a side product of the reaction as shown below. To avoid this side product the use of excess reagent guarantees a higher yield of the 1° alkyl halide. Remember protonated alcohols are very poor nucleophiles. H2O OH O OH O H S OH OH2 O S N2 Reaction O