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Thermometer Adapter with Drying Tube

OrganicChemistry323A — Fri, 7 Aug 2009 21:16:51 MDT

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Thermometer Adapter with Drying Tube - IMG_1221.jpg

Thermometer Adapter with Drying Tube

OrganicChemistry323A — Fri, 7 Aug 2009 21:16:08 MDT

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Thermometer Adapter with Drying Tube - IMG_1221-1.jpg

Vacuum Adaptor

OrganicChemistry323A — Fri, 7 Aug 2009 21:10:49 MDT

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Vacuum Adaptor - SimpleDistillation-adaptor.jpg

Vacuum Adaptor

OrganicChemistry323A — Fri, 7 Aug 2009 21:09:47 MDT

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Vacuum Adaptor - SimpleDistillation-adaptor-1.jpg

Buchner Funnel

OrganicChemistry323A — Fri, 7 Aug 2009 21:03:18 MDT

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Buchner Funnel - BuchnerFunnel.jpg

Buchner Funnels are used to collect recrystalized compounds during filtration.

Buchner Funnel

OrganicChemistry323A — Fri, 7 Aug 2009 21:02:00 MDT

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Buchner Funnel - BuchnerFunnel-1.jpg

Buchner Funnels are used to collect recrystalized compounds during filtration.

5. Fire Shower

OrganicChemistry323A — Fri, 7 Aug 2009 19:59:37 MDT

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5. Fire Shower - FireShowerDone.jpg

The Fire Shower is located by the eyewash facilities. Pull the lever on the wall to activate. Do not worry about causing a flood in an emergency, but do not use if there is no emergency - there is no drain.

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OrganicChemistry323A — Fri, 7 Aug 2009 19:59:36 MDT

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5. Fire Shower

OrganicChemistry323A — Fri, 7 Aug 2009 19:58:14 MDT

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5. Fire Shower - 5-1.jpg

14 Arrow on lid

OrganicChemistry323A — Tue, 4 Aug 2009 22:09:23 MDT

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14 Arrow on lid - DSC_0948.jpg

Infrared Spectrophotometer. The entire set up of hardware and lab procedures are presented here. Prior to coming to the lab, students should read the textbook and understand the theories associated with the instrument. Before putting in a sample, it one MUST run a background spectrum for the air, with the lid closed. The air contains carbon dioxide, which also absorbs IR. By running the background (air absorption), you can "tare" the readings before absorption peaks of a real sample's are collected.

14

OrganicChemistry323A — Tue, 4 Aug 2009 22:08:07 MDT

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14 - DSC_0948-1.jpg

Septum

OrganicChemistry323A — Tue, 4 Aug 2009 21:51:25 MDT

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Septum - DSC_1130-1.jpg

Glass (Draw Arrow) Stopper

OrganicChemistry323A — Tue, 4 Aug 2009 21:39:26 MDT

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Glass (Draw Arrow) Stopper - DSC_0919.jpg

This is used with the Separatory Funnel. It is part of the "Organic glassware w/ 19/22 joints" in your Equipment List. Be sure that you test to see if it fits properly with your Separatory Funnel BEFORE you conduct your Extraction! Otherwise you will LOSE your liquid and have to START OVER!

Glass Stopper

OrganicChemistry323A — Tue, 4 Aug 2009 21:37:32 MDT

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Glass Stopper - DSC_0919-1.jpg

Adaptor, rubber (Need arrow)

OrganicChemistry323A — Tue, 4 Aug 2009 21:33:49 MDT

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Adaptor, rubber (Need arrow) - VacuumAdaptorFinsihed.jpg

The Vacuum Adaptor ensures that the funnel and the vacuum are snug. This is used during Simple Distillation.

Adaptor, rubber

OrganicChemistry323A — Tue, 4 Aug 2009 21:31:59 MDT

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Adaptor, rubber - VacuumAdaptorFinsihed-1.jpg

The Vacuum Adaptor ensures that the funnel and the vacuum are snug. This is used during Simple Distillation.

7 Remove pipet and make solid yellow color

OrganicChemistry323A — Tue, 4 Aug 2009 19:39:11 MDT

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7 Remove pipet and make solid yellow color - NitrationofBromobenzene015-1.jpg

The purpose of this photo is to demonstrate the use of a utility clamp to hold the flask in place. The solid seen in this photo came from a different experiment (benzoic acid). While waiting for the solid to crystallize, always place a stopper to prevent solvent evaporation and potential contamination. At the same time, prepare a vacuum filtration set-up to collect the crystals.

7 want brown solution in the funnel

OrganicChemistry323A — Tue, 28 Jul 2009 11:57:39 MDT

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7 want brown solution in the funnel - DSC_0914.jpg

Re-extract the brown solution once or twice by adding another portion(s) of fresh solvent (water in this case) into the brown organic layer. Shake and vent as usual.

6 Make top layer brown

OrganicChemistry323A — Tue, 28 Jul 2009 11:57:38 MDT

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6 Make top layer brown - DSC_0966.jpg

After the bottom layer is drained, the top layer remaining in the separatory funnel is the organic layer.

1 Need arrow

OrganicChemistry323A — Tue, 28 Jul 2009 11:57:37 MDT

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1 Need arrow - MiscExperiment003.jpg

Important tips: (1) Separatory funnels should always be stored with the glass cap detached. Glass pieces tend to stick together at the joints over time. (2) Before using the separatory funnel, turn the stopcock a few times and leave it in the close position. Add a small amount of acetone from the top so you can test if the stopcock is leaking when the apparatus is placed in an upright position. (3) Put the stopper (cap) on, invert the apparatus, and make sure no leaking from the cap occurs as well. (4) The blue screw can be adjusted to make the stopcock tightened or loosened. (5)If the cap leaks slightly (which is common), try to hold the apparatus horizontally, instead of pointing the narrow tip upwards when you use the apparatus. (6) It is important to vent occasionally to release the vapor pressure of solvent by turning the stopcock (valve) during extraction. Failure to vent the pressure usually results in cap-popping, which not only causes chemical spillage, it is also a major safety issue. (7) After use, the entire piece must be dissembled, thoroughly washed and dried, and then stored detached in the drawer.

14 Want the middle spot smaller

OrganicChemistry323A — Tue, 28 Jul 2009 11:52:23 MDT

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14 Want the middle spot smaller - cb.jpg

Again, keep the plate inside the hood, spot the results from the iodine chamber immediately. The plate in this photo came from the experiment "an oxidation-reduction scheme". Q: How do you determine Rf- retardation factor?

12 Smaller spots

OrganicChemistry323A — Tue, 28 Jul 2009 11:52:22 MDT

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12 Smaller spots - thNitrationofBromobenzene014.jpg

Circle the spots by pencil under UV lamp immediately.

11 Make spots smaller

OrganicChemistry323A — Tue, 28 Jul 2009 11:52:21 MDT

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11 Make spots smaller - thNitrationofBromobenzene015.jpg

Sometimes, the result may not be visible to your naked eyes. After solvent evaporated, try visualization methods to help you view the spots, e.g. under ultraviolet (UV) lamp, if the compound fluoresces under UV light. The plate in photo came from the experiment "nitration of bromobenzene". The spots were purposely made large for a better photo-image.

8 Eliminate lines

OrganicChemistry323A — Tue, 28 Jul 2009 11:52:20 MDT

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8 Eliminate lines - IMG_0239-1-1-1.jpg

For a clear photo-image, the spot size was purposely made bigger here, compared to the ideal 2 mm diameter, which is usable. If the pipet is held to the plate, its entire contents will be delivered to the plate. Proceed to apply the second and third spots, with new capillary tubes for another two samples, keeping the amount of material spotted consistent.

7 Elimiate thr lines on blank plate on the left

OrganicChemistry323A — Tue, 28 Jul 2009 11:52:19 MDT

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7 Elimiate thr lines on blank plate on the left - fixedgel.jpg

Spotting: Use a capillary tube to receive sample solution. The tube has two end-openings, which is unlike the one-end-sided melting column. Important: lightly and briefly touch the plate at a point 1 cm from the bottom. It is often helpful to blow gently on the plate as the sample is applied. Ideal spot size is 2 mm in diameter. The smaller the spot formed, the better the separation obtainable. If needed, additional material can be applied by repeating the spotting procedure. Allow the solvent to evaporate between applications. Q: Why does the spot position have to be so high compared to the depth of the development solvent (0.5 cm) in the jar?

10 Eliminate trash from photo

OrganicChemistry323A — Tue, 28 Jul 2009 11:48:28 MDT

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10 Eliminate trash from photo - DSCN3693.jpg

Transfer the solid-containing solution into the Buchner funnel. Gently swirl up the solution to evenly suspend the solid in the solution, then pour. Recrystallized sulfanilamide from ice bath is demonstrated in this photo. The color of the crystal may look off-white, and the following two steps are commonly taken at this stage (1) Add a small amount of ice-cold solvent to rinse out the solid from the flask to empty out all the crystal formed. (2) To completely wash off the impurity, spread the solid and pipet another small amount of ice-cold solvent on top of the colored solid as shown by the next photo.

13 Need change: MAKE SOLID WHITE

OrganicChemistry323A — Tue, 28 Jul 2009 11:48:11 MDT

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13 Need change: MAKE SOLID WHITE - IMG_0329.jpg

To squeeze the solvent out of the solid, place another pre-weighed filter paper on top of the pure crystals. Note: the purpose of this photo is to show an additional step that is taken to help the solid dry faster. The colored crystals actually came from a different experiment.

5 Arrows

OrganicChemistry323A — Tue, 28 Jul 2009 11:46:01 MDT

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5 Arrows - IMG_0175.jpg

Use aluminum foil on the septum and the three-way distillation head to fix the thermometer tip. Position the thermometer tip below the side arm, making sure it is free from glass-wall touching for accurate temperature readings. Again, the thermometer is to take temperature for vapor, not for liquid underneath. Because the distilling flask will be exposed to high heat-input, the lower metal clamp (i.e. utility clamp) is crucial in order to constantly hold the round bottom flask in place during the entire distillation process, or even when the heating mantle has to be dropped to help cooling. The upper utility clamp is redundant, although acceptable. Blue plastic clamp may melt at high temperatures. Note the fatter end of the blue clamp which fastens the condenser.

3 Arrows and names of each piece

OrganicChemistry323A — Tue, 28 Jul 2009 11:46:00 MDT

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3 Arrows and names of each piece - DSC_1130.jpg

To record vapor temperature, the thermometer is connected on top of the 3-way adapter (i.e. distillation head) by using a septum (orange rubber adapter). A condenser is attached to the distillation head. To make sure that thermometer tip is held steady, you may use aluminum foil to wrap around the septum, as can be seen in the next photo.

7

OrganicChemistry323A — Mon, 27 Jul 2009 17:46:58 MDT

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7 - NitrationofBromobenzene015-1-1.jpg

10.

OrganicChemistry323A — Mon, 27 Jul 2009 00:46:57 MDT

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13.

OrganicChemistry323A — Mon, 27 Jul 2009 00:46:53 MDT

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OrganicChemistry323A — Mon, 27 Jul 2009 00:46:50 MDT

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With an additional piece of filter paper to sandwich the finished solid and use a flat object (e.g. beaker), apply pressure to assist solvent removal.

6.

OrganicChemistry323A — Mon, 27 Jul 2009 00:46:47 MDT

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Vacuum Filtration Apparatus Set-up: to avoid glassware breakage, carefully CLAMP DOWN these pieces on the ring stands. (Right) The Buchner funnel is first placed on top of the filter flask. Use ONLY black rubber hoses to connect to the vacuum line. A "vacuum trap" is attached between the filter flask and vacuum valve on the wall. This vacuum trap is absolutely indispensable to protect the vacuum pump from chemical attacks in case the liquid overflows in the filter flask.

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OrganicChemistry323A — Mon, 27 Jul 2009 00:46:44 MDT

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To ensure an efficient vacuum line, be sure to install a vacuum adaptor (e.g. black rubber sleeve) between the Buchner funnel and the filter flask.

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OrganicChemistry323A — Mon, 27 Jul 2009 00:45:46 MDT

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OrganicChemistry323A — Mon, 27 Jul 2009 00:45:44 MDT

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After the bottom layer is drained, the top layer remaining in the separatory funnel is the organic layer.

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OrganicChemistry323A — Mon, 27 Jul 2009 00:45:42 MDT

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Re-extract the brown solution once or twice by adding another portion(s) of fresh solvent (water in this case) into the brown organic layer. Shake and vent as usual.

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OrganicChemistry323A — Mon, 27 Jul 2009 00:43:36 MDT

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OrganicChemistry323A — Mon, 27 Jul 2009 00:43:32 MDT

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Circle the spots by pencil under UV lamp immediately.

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OrganicChemistry323A — Mon, 27 Jul 2009 00:43:30 MDT

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OrganicChemistry323A — Mon, 27 Jul 2009 00:41:04 MDT

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OrganicChemistry323A — Mon, 27 Jul 2009 00:39:33 MDT

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OrganicChemistry323A — Mon, 27 Jul 2009 00:38:21 MDT

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OrganicChemistry323A — Thu, 23 Jul 2009 10:44:32 MDT

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OrganicChemistry323A — Thu, 23 Jul 2009 10:43:55 MDT

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Vial

OrganicChemistry323A — Wed, 22 Jul 2009 11:39:32 MDT

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Vial - VIAL2.jpg

A Vial can collect distillate or be used to store your product in your drawer (as appropriate).

3

OrganicChemistry323A — Tue, 21 Jul 2009 10:48:13 MDT

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3 - IMG_0707.jpg

Remember, one extraction step will not transfer all the benzoic acid from the original binary mixture solution to the aqueous layer. You always need to re-extract the original solution using the same 3M NaOH(aq) again. In this case, the organic layer is put back into the separatory funnel. Add a second portion of 3M NaOH(aq) to "shake and vent" again (re-extract). The majority of benzoic acid will be removed from the organic layer after this. There is no need to wash the separatory funnel between extraction steps until you completely finish the extraction procedures.

5 Clean up the backgroud mess?

OrganicChemistry323A — Mon, 20 Jul 2009 19:08:29 MDT

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5 Clean up the backgroud mess? - DSC_0981.jpg

Pour the mixture to be filtered onto the filter paper.

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OrganicChemistry323A — Mon, 20 Jul 2009 14:29:08 MDT

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If the lab ran out of iron rings with rubber cushions, use a cork ring for protection. There are two layers to be seen. Look up density of methylene chloride. This will help you determine whether the bottom layer is an organic layer. Note: Water density is 1.00g/mL at 25 C. You can also test solubility by pipetting one drop of water into the bottom layer to confirm. Be certain to label and save both layers from both extraction steps. Again, you can't drain the liquid unless the top stopper is removed.

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OrganicChemistry323A — Mon, 20 Jul 2009 14:26:27 MDT

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A small flask can be used to apply pressure on top of the filter paper.

RE-Extraction

OrganicChemistry323A — Mon, 20 Jul 2009 14:22:59 MDT

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RE-Extraction - DSC_0960.jpg

Remember, one extraction step will not transfer all the benzoic acid from the original binary mixture solution to the aqueous layer. You always need to re-extract the original solution using the same 3M NaOH(aq) again. In this case, the organic layer is put back into the separatory funnel. Add a second portion of 3M NaOH(aq) to "shake and vent"- extract again. The majority of benzoic acid will be removed from the organic layer after this. There is no need to wash the separatory funnel between extraction steps until you completely finish the extraction procedures.

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OrganicChemistry323A — Mon, 20 Jul 2009 14:22:54 MDT

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The methylene chloride is ready to be combined with the sodium hydroxide.

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OrganicChemistry323A — Mon, 20 Jul 2009 14:22:22 MDT

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OrganicChemistry323A — Mon, 20 Jul 2009 14:22:12 MDT

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Hexane is heated (the appropriate amount of mls based on the weight of the crude product). It will be used in the re-crystallization of triphenylmethane.

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OrganicChemistry323A — Mon, 20 Jul 2009 13:12:04 MDT

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Wrap up and save your two solids for melting point experiment next week. Use a pencil to label each compound. Always allow the solids to dry at least overnight before determining melting points and yields.

13

OrganicChemistry323A — Mon, 20 Jul 2009 13:00:13 MDT

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Gravity Filtration - for hot triphenylmethane-hexane solution.

7

OrganicChemistry323A — Mon, 20 Jul 2009 12:35:58 MDT

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To the organic layer, add ~0.5 g of anhydrous sodium sulfate and swirl the resulting suspension for a few minutes to remove the water from the extraction. This layer contains triphenylmethane in methylene chloride.

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OrganicChemistry323A — Mon, 20 Jul 2009 12:18:21 MDT

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Watchglass used to pour crude product onto.

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OrganicChemistry323A — Mon, 20 Jul 2009 12:03:53 MDT

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Proceed to collect benzoic acid precipitate by vacuum filtration. As an optional experiment, recrystallize the benzoic acid from hot water. Be sure to visit "Vacuum Filtration" and "Crystallization" albums for important tips. Q: How do you dispose of the filtrate?

11. Acid-Base Station

OrganicChemistry323A — Mon, 20 Jul 2009 12:02:04 MDT

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11. Acid-Base Station - Acid-basestationcomplete.jpg

You will find the acids and bases you will need at the Acid-Base Station. Be sure to always put the lids back on tightly after use! Be sure to always keep acids and bases separated. Note that in this picture, students left the area without cleaning up. Keep your station clean! Always exercise caution around acids and bases.

9.

OrganicChemistry323A — Mon, 20 Jul 2009 11:42:11 MDT

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9. - NitrationofBromobenzene.jpg

For crystallization: Add 5 mL ethanol per gram of crude product(s), add boiling chips, swirl on hot plate, and boil to dissolve the crude product. Allow it to cool slowly to room temperature.

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OrganicChemistry323A — Mon, 20 Jul 2009 00:03:04 MDT

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After combining two portions of the aqueous layers from extraction, convert this aqueous solution of sodium benzoate to benzoic acid by adding concentrated HCl(aq) until the solution is acidic to litmus paper (pH paper), turning blue to red. Being insoluble in cold water, benzoic acid precipitates will form under acidic condition. To help you achieve the equivalent point and then PH below 7 efficiently, you must precalculate the appropriate volume of concentrated HCl(aq) needed to neutralize your basic extract. Make sure the solution is kept in the ice bath to cool down neutralization heat. Constantly stir with a glass rod. Do NOT use metal spatula for stirring acids or bases.

1

OrganicChemistry323A — Mon, 20 Jul 2009 00:02:54 MDT

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Be aware that this experiment is particularly time-consuming. In order to work efficiently in the lab, you must fully understand each step before coming to the lab. The first step of this extraction experiment is to separate benzoic acid from a binary mixture of triphenylmethane and benzoic acid, both predissolved in methylene chloride. When you add two portions of NaOH(aq) during extraction, only benzoic acid can transfer into aqueous phase through the formation of water-soluble ions of sodium benzoate (via an acid-base neutralization reaction). You must precalculate the theoretical amount (volume) of 3M NaOH for this step. Triphenylmethane will always remain in methylene chloride solution, the organic layer. The two compounds thus isolated are then purified by crystallization.

NitrationofBromobenzene025-1.jpg

OrganicChemistry323A — Sun, 19 Jul 2009 23:49:06 MDT

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OrganicChemistry323A — Sun, 19 Jul 2009 23:49:00 MDT

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Erlenmeyer Flask

OrganicChemistry323A — Sun, 19 Jul 2009 09:42:33 MDT

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Erlenmeyer Flask - IMG_0336.jpg

piperanisaldehyde crystals

Round Bottom Flask

OrganicChemistry323A — Sun, 19 Jul 2009 09:38:53 MDT

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Round Bottom Flask - IMG_0241.jpg

Round Bottom Flask

OrganicChemistry323A — Sun, 19 Jul 2009 09:26:33 MDT

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Round Bottom Flask - IMG_0237.jpg

An oily camphor layer floats on the top of the reaction mixture, whereas the bottom aqueous layer also contains camphor and other compounds (such unreacted reactants, acid, by products etc). Run a TLC test for the bottom layer to confirm disappearance of borneol from the reaction mixture.

21. Heating Mantle

OrganicChemistry323A — Sat, 18 Jul 2009 21:19:25 MDT

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21. Heating Mantle - IMG_0102.jpg

Connect the heating mantle into the Variac as such and turn the knob on the Variac to regulate heat input. Warning: Never connect heating mantle directly to the wall without plugging into Variac first. The power plug on the wall only provides 100% heat output making heating mantle extremely hot! This is a serious fire hazard, especially when heating a flammable fluid.

Cork Ring

OrganicChemistry323A — Sat, 18 Jul 2009 20:01:32 MDT

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Cork Ring - DSC_0971.jpg

Beaker

OrganicChemistry323A — Sat, 18 Jul 2009 15:42:31 MDT

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Beaker - IMG_0099.jpg

1. Lab Safety Intro

OrganicChemistry323A — Sat, 18 Jul 2009 09:55:05 MDT

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1. Lab Safety Intro - IntroSafety2.jpg

Your safety is paramount. This slideshow gives a basic introduction on safety - you must listen to the instructions your lab instructor will give. The first class session will involve an overview of safety measures. Each session, practice safety and caution. Seek help from your lab instructor even if there is only a slight chance that a problem exists. See Technique 1 in the lab manual for details - this is required reading.

2. Lab Attire

OrganicChemistry323A — Sat, 18 Jul 2009 09:42:00 MDT

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2. Lab Attire - eyesafety-1.jpg

Wear goggles, gloves, tie shoulder length and longer hair back, and wear closed toe shoes. Your goggles must be approved BEFORE the first lab experiment. ALWAYS wear approved safety goggles or safety glasses within a laboratory, even when glassware washing. The only exception to not wearing goggles in lab is when no one is handling chemicals or using the instruments (e.g. during the instructor's pre-lab lecture). Also, wear gloves to minimize exposure. The stock room has a limited amount available. These gloves do not protect against heat.

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OrganicChemistry323A — Thu, 16 Jul 2009 19:52:28 MDT

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OrganicChemistry323A — Tue, 14 Jul 2009 20:44:04 MDT

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OrganicChemistry323A — Tue, 14 Jul 2009 20:42:41 MDT

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Condenser

OrganicChemistry323A — Tue, 14 Jul 2009 20:14:49 MDT

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Condenser - CondensorFinished.jpg

The distillate can travel through the condenser and will be cooled off as it moves. See "Distillation".

Centrifuge Tube

OrganicChemistry323A — Tue, 14 Jul 2009 20:13:46 MDT

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Centrifuge Tube - CentrifugeTubeFinished.jpg

See "Extraction of Chlorophyll"

Wash Bottle (Bottle, wash)

OrganicChemistry323A — Tue, 14 Jul 2009 19:29:34 MDT

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Wash Bottle (Bottle, wash) - washbottleFinsihed.jpg

Wash Bottles are helpful in cleaning glassware.

Test Tube Rack (Rack, test tube)

OrganicChemistry323A — Tue, 14 Jul 2009 12:54:29 MDT

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Test Tube Rack (Rack, test tube) - IMG_1114.jpg

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OrganicChemistry323A — Tue, 14 Jul 2009 08:32:20 MDT

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Find the vacuum line switch on the wall when connecting black rubber hoses.

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OrganicChemistry323A — Sun, 12 Jul 2009 22:55:10 MDT

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OrganicChemistry323A — Sun, 12 Jul 2009 22:40:02 MDT

OrganicChemistry323A posted a photo

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OrganicChemistry323A — Sun, 12 Jul 2009 22:11:59 MDT

OrganicChemistry323A posted a photo

NitrationofBromobenzene013.jpg

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OrganicChemistry323A — Fri, 10 Jul 2009 18:16:41 MDT

OrganicChemistry323A posted a photo

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Foil is commonly used to cover the fractional distillation column, and the distilling flask, but not on the condenser. Revisit the simple distillation album for the same important tips.

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OrganicChemistry323A — Fri, 10 Jul 2009 18:16:40 MDT

OrganicChemistry323A posted a photo

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Properly secure the thermometer and connect the rubber tubing on the condenser. Again, cold water enters from the bottom of the condenser.

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OrganicChemistry323A — Fri, 10 Jul 2009 18:16:39 MDT

OrganicChemistry323A posted a photo

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The vacuum adaptor is then connected to the condenser and secured with a blue clip.