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Appearance: colorless to light yellow liquid with a pungent and choking dour Melting point: -112 C Boiling point: 51 C Vapor density: 2. 7 Vapor pressure: 315 MBA at 20 C Density (g CM-3): 1. 104 Flash point: 4 C (closed cup) Explosion limits: 7. 3% – 19% Continuation temperature: 390 C Water solubility: decomposes aluminum chloride SACS #7446-70-0 Physical State: Crystalline powder Color: yellow – fine Odor: acrid odor – strong odor pH: Not available Vapor Pressure: 0. 004 MBA @ 50 deg C Vapor Density: Not available Evaporation Rate: Not available Viscosity: Not available

Boiling Point: Not available Freezing/Melting Point: 194 deg C ( 381. OFF) Decomposition Temperature: Not available Solubility in water: Reacts Specific Gravity/Density: 2. 440 Molecular Formula: ACACIA Molecular Weight: 133. 34 anthracite SACS #120-12-7 Appearance: off-white to pale green crystals Melting point: 215 – 219 C Boiling point: 340 C Specific gravity: 1. 25 Vapor pressure: Flash point: 121 C (closed cup) Explosion limits: 0. 6% (lower) Continuation temperature: anhydrous calcium chloride SACS #10043-52-4 Appearance: white beads or powder Melting point: 782 C

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Boiling point: Vapor density: Vapor pressure: negligible Specific gravity: 2. 15 Flash point: Explosion limits: anhydrous chloroform (no stabilizer) SACS #67-66-3 Appearance: clear colorless liquid with a sweet dour Melting point: -63 C Boiling point: 61 C Vapor density: 4. 1 Vapor pressure: 159 mm Hag at 20 C Specific gravity: 1. 48 g cam Flash point: none Water solubility: 8 g/l at 20 C Refractive index: 1. 4459 at 20 C, 589 NM concentrated hydrochloric acid SACS #7647-01-0 Appearance: clear colorless or slightly yellow liquid with pungent dour. Concentrated acid is fuming.

Melting point: -25 C Boiling point: 109 C Specific gravity: 1. 19 anhydrous magnesium sulfate SACS #7487-88-9 Appearance: solid Melting point: Density (g CM-3)1 1. 07 Water solubility: saturated sodium bicarbonate SACS #144-55-8 Appearance: white powder or crystals Melting point: 50 C Density (g CM-3): 2. 16 C. Chemical Reaction: Session 1 Session 2 D. Data and Result Look at appendix E. Discussion and Conclusion Session 1 (Partner up for this lab): We assembled a drying tube. Into a clean dry 50 ml round-bottom flask, we added 2. 0 g of anthracite and 15 ml of anhydrous chloroform.

We made an ice- water bath in a beaker that will hold the 50 ml round-bottom flask and placed the ice-water bath on a stir plate in the hood. We had to do the following things as quickly as possible: weighing approximately 3 g of aluminum chloride and adding it to the 50 ml round-bottom flask, also placing a septum securely over the neck of the round-bottom flask and plunge the needle of the drying tube into the septum. We clamped the round-bottom flask in the ice-water bath that we put in the hood. We placed a disposable needle on a 10 ml plastic syringe and used it to take up 4. L of acetylene chloride. We stuck the acetylene chloride syringe through the septum on the flask and added the acetylene chloride slowly while stirring so that the reaction does not heat up too much -probably over the course of about 20 minutes. Later the acetylene chloride syringe was removed from the septum and allowed the reaction to stir for approximately 20 more minutes in the ice bath. We rinsed the 10 ml syringe with water and collect the water for naturalization with sodium bicarbonate, where we collected most aqueous solutions together for naturalization until the end of the lab.

We placed 1″ polygon stir bar in the beaker with the ice and reaction mixture and began stirring. Later slowly added concentrated hydrochloric acid until the white precipitate clears and we had a translucent solution. We poured the contents of the beaker into a 125 ml separators funnel. We drained off the chloroform layer into a clean 125 ml Erlenmeyer flask. We extracted two times with 15 ml aliquots of chloroform, draining the chloroform layers into the 125 ml Erlenmeyer. We retained about 0. 5 ml of this mixture in a small test tube for TTL. Add the chloroform solution back into the separators funnel.

Slowly add 20 ml of saturated sodium bicarbonate solution to the separators funnel. The reaction will produce carbon dioxide gas, so add the sodium bicarbonate slowly. With the stopper off,we swirled the separators funnel. Then cap it and shake lightly. We drain the chloroform layer into the original Erlenmeyer and added the aqueous solution slowly to the solutions to be neutralized. Bubbles were form when adding to the acetylene chloride rinses previous collected. We continue to wash with 20 ml aliquots of sodium bicarbonate as above until the solution does not evolve carbon dioxide gas..

The solution was fully neutralized when the addition of solid sodium bicarbonate no longer results in the formation of bubbles. We added enough anhydrous magnesium sulfate to dry the chloroform solution in the 125 ml Erlenmeyer. We filtered the solution using a Bјcaner funnel and filter paper into a 125 ml filter flask. Place the magnesium sulfate in the “Used Magnesium Sulfate” container and toss the filter paper. I took the filtrate to rattrap and ran an NOR, while my partner ran a TTL. For second session, we weighed 0. 5 g of 9-oxyacetylene’s into a 50 ml round- bottom flask.

We saved the remaining 9-oxyacetylene’s for TTL and added 15 ml of chloroform to the round-bottom flask. Additionally, we added 2. 6 g of 3- chlorofluorocarbon acid (masc..) to the chloroform solution. We placed the round- bottom flask in a clamp above a stir plate and begin stirring gently for 1 hour at room temperature. We placed the reaction in a 125 ml separators funnel. We extracted the reaction 5 times with 20 ml aliquots of 1 M sodium hydroxide. We use a 25 ml Erlenmeyer flask to collect the chloroform layer each time and a 125 ml Erlenmeyer flask to collect the aqueous washes.

We dried the chloroform layer with sodium sulfate anhydrous and filter the chloroform solution using a Bјcaner funnel and filter paper into a 125 ml filter flask. We reserve about h ml of the chloroform solution in a small test tube for a TTL, while one partner takes the filtrate to rattrap and ran an NOR. F. Questions: Session l: 1 Download and print a spectrum of anthracite from BMW. Sigma-Aldrich. Com. Label the peaks in the spectrum of your product that are due to your product? 2. ) What was the gas evolved when you extracted the reaction mixture with saturated sodium bicarbonate?

The gas evolved when we extracted the reaction mixture with saturated sodium bicarbonate was Carbon did oxide. 3. ) What product would you expect if the reaction got too warm? If the product is warm then we would be expecting oxyacetylene and HCI as the product since the acid base reaction leads to exothermic reaction. 4. ) How many equivalents of ACACIA did you use? Explain why in terms of the mechanism for this reaction? We used 3. 001 grams of ACACIA. As the following mechanism indicates, Frilled-Crafts collation involves the formation of an calcium ion as the active electroscopic species.

The reactive calcium ion is generated from an call halide or anhydride. Aluminum chloride is commonly used for this purpose. Although ACACIA could potentially affect the catalysis of the Frilled-Crafts collation reaction, the product, a ketene, is sufficiently basic enough to interact strongly with ACACIA such that more than one equivalent of ACACIA is required. The CAB is removed in the aqueous workup step by hydrolysis to HCI and aluminum hydroxide. 5. ) Would the resonance for the methyl group on the acetylene moiety be more downfalls or field on the NOR spectrum in the distillate product versus the inoculated product?

The resultant calculated shifts for the assigned resonances were in good agreement with the observed shifts, the shifts of the CHI groups near the BEEF site were then calculated from their geometry in this axis system and the best fit AAA and AAA. The choice of axis system was then rejected if it did not meet the criterion of having only two methyl groups shifted more downfalls than 10 pomp, and no methyl resonance shifted more field than -5 pomp. Session II: 1 . ) Draw a representation of your TTL from this reaction. Label each spot. 2. ) Write the mechanism for the Brayer-Villager reaction.

What are the products of the reaction you performed? 3. ) What do you think the purpose of the sodium hydroxide washes is? The sodium hydroxide is used to improve the percent yield, as well as, to remove sulfurous impurities in a process known as caustic washing. As above, sodium hydroxide reacts with weak acids such as hydrogen sulfide and merchantman to give the non-volatile sodium salts which can be removed. 4. ) Why is the chloroform layer the bottom layer when performing extractions? Chloroform has a density of 1. 48 g/ml so the chloroform will be the bottom layer.

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