CH361/361H Week 5 Lecture Synthesis of. 2,3-Dimethylbutene Isomers. Identify unknown. carboxylic acid
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1 sodium salt of unknown aromatic carboxylic acid + soluble impurities + insoluble impurities total mass:? g insoluble impurities mass:? g dissolve in water, filter aq. sol n of unk. sodium salt + sol. impurities decolorize, filter account for all masses; calculate %recovery 361/361 Week 5 Lecture Synthesis of Identify unknown carboxylic acid 2,3-Dimethylbutene Isomers colored dye(s) mass: ~ 20 mg aq. sol n of unk. sodium salt + sol. impurities conc. l; filter mp, MW, pk a, derivative mp water-soluble imp. crude unk. carboxylic acid mass:? g recrystallize pure unk. carboxylic acid mass:? g melting point ( mp )
2 Experiment II verview: reparation & Equilibration of Isomeric 2,3-Dimethylbutenes cat K eq =? ΔG =? Δ =? ΔS =? 2,3-dimethyl-2-butene 2-ene 2,3-dimethyl-1-butene major activities in experiment II RERT 2 synthesis of 2-ene (major) / mixture by Grignard reaction followed by acid mediated dehydration (E1 elimination) last name starts with M-Z synthesis of by Wittig olefination last name starts with A-L purification and isomer separation by distillation / fractional distillation RERT 3 equilibration of alkene isomers and analysis of alkene isomer distributions by gas chromatography (G) determination of thermodynamic properties (DG, D, DS ) by analyzing temperature dependence of equilibrium constant (K eq )
3 Synthetic Strategy: ow to Make Alkenes from 3-Methylbutanone δ δ+? + 3-methylbutanone "2-ene" "1-ene" 3 3 -centered nucleophile -centered electrophile
4 Grignard Reaction/Dehydration: 1. Formation of Grignard / Addition to Ketone 3 δ+ δ Mg magnesium metal δ δ+ 3 I 3 MgI δ δ+ iodomethane (methyl iodide) diethyl ether (Et 2 ) methylmagnesium iodide (a synthetic equivalent of methyl carbanion) S 3 + p-toluenesulfonic acid aq. l MgI 2-ene major product minor product F. A. Victor Grignard winner of 1912 Nobel rize 2,3-dimethylbutan-2-ol purified by simple distillation magnesium alkoxide
5 Grignard Reaction/Dehydration: 2. Dehydration Reaction (E1 Elimination) tertiary (3 ) carbocation 2 S 3 + p-toluenesulfonic acid 2-ene major product bp. 72 minor product bp. 56 separated by fractional distillation 2,3-dimethylbutan-2-ol purified by simple distillation
6 Experimental Set-Up for Grignard Reaction (IN FUME D) READ SAFETY NTE iodomethane is a cancer suspect agent; ALL WRK IN D! (wear proper E); RB will depense iodomethane into press. equal. funnels for you diethyl ether is highly flammable; Grignard reagents are potentially pyrophoric important that glassware is dried in oven, assembled quickly, and flushed with nitrogen BEFRE finishing on Wed., leave glassware in metal bowl ready to be oven dried before Friday s lab
7 Wittig lefination to Generate Directly Na Br NaMe 2 Et sodium tert-pentoxide MeN NBu BF 4 methyltriphenylphosphonium Georg Wittig bromide winner of 1979 Nobel rize bmim + BF an ionic liquid methylenetriphenylphosphorane a phosphorus ylide 2 h + 3 h 3 2 h 3 triphenylphosphine oxide the oxaphosphetane the betaine (a zwitterion)
8 Wittig lefination to Generate Directly Na Br NaMe 2 Et sodium tert-pentoxide MeN NBu BF 4 methyltriphenylphosphonium bromide bmim + BF an ionic liquid methylenetriphenylphosphorane a phosphorus ylide 2 h + 3 h 3 2 h 3 triphenylphosphine oxide the oxaphosphetane the betaine (a zwitterion)
9 Experimental Set-Up for Wittig lefination (on bench) YUR LAB MANUAL NTAINS LDER REDURE BE SURE T LLET ANDUT TDAY (p ) READ SAFETY NTE use of dust mask is ESSENTIAL to avoid unintended inhaltion of finely powdered sodium tertpentoxide; other E as usual (gloves, lab coat, goggles) important that glassware is dried in oven, assembled quickly, and flushed with nitrogen BEFRE finishing on Wed., leave glassware in metal bowl ready to be oven dried before Friday s lab
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