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Notes0618 - liquid that is being boiled 5 Collecting flask...

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Experiment 4: Synthesis of Cyclohexene General Reaction R R R R OH H 3 PO 4 (conc.) R R R R heat + H 2 O or H 2 SO 4 (conc.) The reaction proceeds by an E 1 mechanism where the rate of the reaction is determined by the formation of the carbocation. Formation of Cyclohexene from Cyclohexanol + H 2 O OH heat H 3 PO 4 (conc.) Mechanism: cyclohexyl dihydrogen phosphate - OP(OH) 2 O dicyclohexyl ether O O H HO OP(OH) 2 O - OP(OH) 2 O - OP(OH) 2 O H OH 2 H OH 2 OH By Products The major product is determined by using Zaitsev’s rule that states the more substituted the alkene the more stable it is. 24
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Stability of Alkenes R R R R R R R R R R R R R R Carbocation stability: Ph 3 C Ph 2 CH PhCH 2 R 2 C CCR 2 R R 2 C CCHR R 2 C CCH 2 R 3 C R 2 CH RCH 2 CH 3 R 2 C CR R 2 C CH Ph Examples: 25
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Ph 2 C CH 3 CHPh OH Ph 2 C CH 3 CHPh Ph 2 C CPh CH 3 H Ph 2 C CPh CH 3 OH H 3 PO 4 heat heat major product + OH heat H 3 PO 4 minor H 3 PO 4 Distillation Safety Tips Revisited: 1) Never heat a closed system. 2) Always use 1 or 2 boiling chips. 3) Be careful with hot plate. a) No wires in the trough. b) Turn the hot plate to medium and then adjust as needed. 26
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4) Distilling flask should be twice the size of the volume of
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Unformatted text preview: liquid that is being boiled. 5) Collecting flask should be large enough to hold the liquid being boiled over. 6) Do not distill to dryness. 7) Do not force glassware, especially thermometers. Grease all glass joints. Hazards: Phosphoric acid – corrosive poison Br 2 – corrosive poison Cyclohexane – flammable Cyclohexene – flammable Circle the predominant product of the following reactions: Ph OH Ph Ph Ph Ph Ph heat H 3 PO 4 E D C B A A B C D E H 3 PO 4 heat OH 27 Draw the structure of the reactant(s) or major organic product(s) of each of the following reactions or write N.R for no reaction. Could have more than one answer per box. Show the correct stereochemistry when needed! H 3 PO 4 heat OH heat H 3 PO 4 Ph OH heat H 3 PO 4 OH 28...
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