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Chemicals: toluene, anhydrous aluminum chloride, acetyl chloride, methylene chloride, conc. HCl, 5% NaHCO3,
brine, anhydrous MgSO4 or Na2SO4.
Glassware and equipment: 50 and 100 mL RBF, air condenser, Claisen adaptor, addition funnel, short stem glass
funnel, 60 and125 mL separatory funnels, 150 mL beaker, 50 mL Erlenmeyer flasks, 10 mL graduated cylinder, lab jack, crystallizing dish, magnetic stir bar.
O 1. CH3 H3C
+ CH3 CH3 O
CH3
2. H3O+, H2O
Electrophilic aromatic substitution reactions (EAS) take place between the nucleophilic a- electrons of an aromatic ring and an enhanced electrophile. The intermediate carbocation rapidly goes through elimination of proton to restore the aromatic system. In the case of Friedel-Crafts acylation, the electrophile is an acylium ion, formed by the reaction of an acyl chloride with aluminum chloride. The mechanism is shown in Fig. 1.
O H3C Cl + Cl Al Cl Cl Cl O H3C CH3 H O + -AlCl3/HCl CH3 CH3 CH3 O CH3 CH3 O CH3 Cl
Cl Al Cl +
O CH3
O H3C
major
minor
Experimental Procedure:
Caution: anhydrous aluminum chloride is moisture sensitive and will irritate your skin producing HCl. Wear gloves and handle this chemical carefully. Close the bottle as soon as you obtain the amount needed. Acetyl chloride is an eye and lung irritant: do not remove from the hood and close tightly after measuring the amount needed. Wash the glassware after this experiment in the hood with some acetone before moving it to your bench top.
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keck clamps
Claisen head
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Crude product
Purified product
Discussion: Yield (5 pt): Explain what could affect the yield of reaction. Be specific and refer to your notebook. TLC (3 pt): compare the TLC of the products and comment on the presence of possible products. IR and NMR (6 pt): when reporting IR and NMR of the products, please do not just list the chemical shifts and the wavenumbers on NMR and IR but rather comment on the changes from one compound to another in terms of reporter peaks. The NMRs of the starting material and the major possible products are presented below: Conclusion (2 pt): comment on any disadvantages or failures of this experiment and propose modifications/improvements for the synthetic procedure. Please be specific and note that general comments such as use a different solvent, different glassware, etc. are not valid to make your point!
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13C
NMR of Toluene:
CH3
4 PPM
150
140
130
120
110
100
90
80 PPM
70
60
50
40
30
20
10
IR of Toluene:
%!
CH3
13C
NMR of p-product:
4 PPM
CH3
O
200 180
CH3
160 140 120 100 80 60 40 20 0
PPM
IR of p-product:
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4 PPM
13C
NMR of o-product:
CH3
O CH3
220
200
180
160
140
120
PPM
100
80
60
40
20
IR of o-product:
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