Orgo Quiz 5 Elimination of Cyclohexene

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9 Terms

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E2

Bimolecular

  • involves a Beta-carbon and an Alpha-carbon


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E1

the cyclohexene lab

  • intermediate carbocation

  • unimolecular

  • bond breaking occurs before double bond formation


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-OH

a poor leaving group because it is a strong base

sulfuric acid protonates the alcohol -→ LG turns into water (better LG then OH)

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Leaving Groups

the weaker the base the better it’s leaving ability

weaker to stronger bases

F> Cl> Br> I (weakest)

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Protonation of an Alcohol

  • improves the LG ability

  • LG- H20, conjugate acid H3O+


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Side reaction

T-butyl alcohol →HCL —→ isobutylene + H2O

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Dehydration of alcohols

cyclohexanol →H2SO4 —→ cyclohexene + H2O

  • forms a H2O and a double bond (alkene)

  • E1


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Experiment 6 Procedure

  • cyclohexanol and sulfuric acid in round bottom flask

  • simple distillation collect distillate 80-85C

  • dry product with CaCl2

  • Distill


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Bromine test

test for double bond after making cyclohexene