Survey
* Your assessment is very important for improving the workof artificial intelligence, which forms the content of this project
Download Document 8195546
Document related concepts
Cracking (chemistry) wikipedia , lookup
Fischer–Tropsch process wikipedia , lookup
Enantioselective synthesis wikipedia , lookup
Marcus theory wikipedia , lookup
Elias James Corey wikipedia , lookup
Discodermolide wikipedia , lookup
Kinetic resolution wikipedia , lookup
Wolff rearrangement wikipedia , lookup
1,3-Dipolar cycloaddition wikipedia , lookup
Physical organic chemistry wikipedia , lookup
Woodward–Hoffmann rules wikipedia , lookup
George S. Hammond wikipedia , lookup
Vinylcyclopropane rearrangement wikipedia , lookup
Asymmetric induction wikipedia , lookup
Ring-closing metathesis wikipedia , lookup
Ene reaction wikipedia , lookup
Diels–Alder reaction wikipedia , lookup
Hofmann–Löffler reaction wikipedia , lookup
Baylis–Hillman reaction wikipedia , lookup
Stille reaction wikipedia , lookup
Tiffeneau–Demjanov rearrangement wikipedia , lookup
Wolff–Kishner reduction wikipedia , lookup
Strychnine total synthesis wikipedia , lookup
Transcript
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
