Tested Overhead Projection Series Compiled by
HUBERT N. ALYEA Princeton University
22. ORGANIC CHEMISTRY
A. General Dem. 6 6 1-Ammonium
Cyanaie fram Urea
To show; Formation of ammonium and cyanate ions by heating urea-aq; a reversal of the classical Wohler's synthesis: (NH)&=O urea
~1NIL,+
+ OCN-
rtrnmo~uumeyanate
Materials: 1 molar urea, device E-1 or Me-amps for measuring current. Procedure: (a) Project two culture tubes half-filled with 1 M urea in H-3. Boil tube B for 5 min. Now transfer the tubes to Me-amps, project, and test for conductivity. (b) Ditto, but add two drops of AgN03aq to each. Observations: (a) The unboiled tuhe (urea) does not conduct; the boiled tuhe (NH,+ and OCN-) conducts. (b) Tube 1, no reaction with Ag+; tube 8 precipitates white (macro) AgOCN. Reference: WALKER, J., and HAMBLEY, 13. J., J. Chem. Soc., 87, 746 (1894); SCHEER, R., P rmis Chem., 5, 56 (1956); SEETHAHAMAN, P. A,, J. Chem. Igduc., 39, A8.19, 1962 uses urea which reverts to ammonium cyanate.
B. Chain Compounds Dem. 662-Amylene
+ Bramine
To shoto: The addition of bromine to unsaturated hydrocarbons. Material:
Bromine, amylene (I-pentene), H-3, cotton.
Procedure: Push a loose wad of steel wool into the bottom half-inch of a culture tube, and to this add four drops of mineral oil. Project in H-3. Heat until white clouds (hydrocarbons) appear. Now tilt an unstoppered bottle of Brs to let the reddish-brown vapor spill into the culture tuhe. Immediately stopper. Let stand a few seconds. Observations: The reddish-brown color disappears. Reason: The steel wool catalyzes the crackiug of the hot oil, giving unsaturated products; the double bonds in the latter add bromine which disappears. Bn 7 CCnHzn A
Reactions:
CnHzn+z
Dem. 664-Cracking
C,H&b
Bacon Fai
To show: The high-temperature cracking of bacon fat, and reaction of the unsaturated products with bromine. Materials: Bacon, forceps, H-3, two culture tube stoppers, bromine. Procedure: Tilt an unstoppered bottle of bromine to spill the vapor into two culture tubes; stopper at once. Project in H-3. Into tube one drop a strip of bacon, about 3 X '/%X in. Holding in the forceps, heat a similar strip of bacon in H-3, and when the bacon sputters and drips, drop it into the bromine in culture tube 2; stopper at once. Observations: Tube 2 becomes colorless in a few seconds. Reason: Heating bacon fat cracks it into unsaturated acrolein (CH,=CH-CHO; this causes the acrid choking odor from burned bacon); the double bond of the unsaturated compound adds bromine, decolorizing the tube. Dem. 665-Preparaiian
To show:
af Aceiylene
Preparation and combustion of acetylene.
Materials:
Fresh calcium carbide, cell H-1.
Procedure: Project two culture tubes in H-3. Tilt an unstoppered bottle of bromine over each, so as to fill them with the reddish-brown vapor; then quickly stopper them with small plugs of cotton. Now put two drops of amylene into tube 2, stopper it again.
Procedure: Project cell H-1 with the generator containing 1 lump (5 mm3, no larger, CARE)of CaC2, and water in the medicine dropper and the receiver. Collect gas in the holder; test with a lighted match.
Observations: Tube 2 becomes colorless as the bromine in i t adds to the unsaturated bond in amylene.
Observations: Acetylene, caught in the gas holder, explodes with air when a match is applied to it.
Reaction: CHFCH-CH1-CH,-CH3 CH2Br-CHBr-CH1-CH3-CH3 Dem. 663-Cracking
+ Br,
-
Mineral Oil
+ +
-+
+
Reactions: CaC2 2HOH Ca(0H)s C%H,t ; 2C2Hz 50%-+ 4C02 2H20. Dem. 666-Acefylene
Formed in a Ballaon
Experiment developed by Ken.neth V. Jaclcman.
Experiment developed by Carl J. Maneuso.
To sh,ow: The cracking of mineral oil, using Fe as catalyst, to give unsaturates which add bromine.
To show: in it.
Materials: Steel wool, H-3, mineral oil, dropper, bromine.
Materials: Rubber balloon, lump of fresh CaCz, thread, medicine dropper, Bunsen burner.
Balloon swelling as acetylene is generated
Volume 46, Number 9 , September 1969
/ A633
+ Cellulose
Procedure: Taking care not to wet the neck of the balloon, squirt a medicine dropperful of water into a rubber balloon. Push a lump of CaCI (0.5 cm3, no larger, CARE)into the neck, and tie shut with thread. Project. Now dump the lump into the water inside the balloon. Throw expanded balloon into a Bunsen flame.
Materials: Soln. A : 5 g soluble cellulose in 100 ml water. S o h . B : light brown solution of iodine in water. Alpha-amylase, cell H-3, stirrer.
Observation: As CzHz is generated, the balloon is filled with gas. Explodes in air when thrown into Bunsen flame.
Procedure: Half-fill two culture tubes with A . Add l g alpha-amylase to tube 2. After 30 min, project in H-3. Add a dropperful of B to each tube.
-
+
-
Reactions: CaCz 2H2O 2C2H2 502 4COI 2H20
+
Reference:
+
LAMAR, W. L.,
Ca(OH)2
+ C2H2;
J. Chem. Educ., 6,2011 (1932).
Dem. 669-Amylase
Experiment developed by Robert Barnard. To show: Cellulose fermented to starch by amylase.
Observations: Tube 1: no coloration, showing starch is not present. Tube 2: hlue coloration due to starch formed from cellulose by fermentation.
C. Ring Compounds
D. Natural Products
Dern. 670--Amylase
+ Starch
Experiment developed by Robert Barnard. Dem. 667-Formic
Acid Swelling Proteins
To' show: How formic acid iu the sting of an insect causes swelling of proteins. Materials: Gelatin, formic acid, hypodermic syringe and needle, phenolphthalein indicator solution; NaOHaq, hotplate, 250 ml beaker, stirrer, H-3. Procedure: Dissolve 5 g gelatin in 100 ml boiling water; to it add four drops indicator a single drop of NaOH to turn it red. Pour into two culture tubes. Let gel. Project in H-3. Plunge the hypodermic needle into the center of each gel, injecting one drop HC1 into tube 1 and one drop of HCOOH into tube Z. Project for 15 min.
+
Observations: Both acids decolorize the red indicator. After some minutes the channel containing the formic acid begins to swell. Dem. 668-Distillation
To show: Starch fermented to sugar by an enzyme, alpha-amylase. Materials: Soln. A: 5 g starch dissolved in boiling water, cooled to room temperature (important) and filtered if necessary to give a clear solution. Soln. B: a light-brown solution of iodine in water. Alphsr amylase, cell H-3. Procedure: Half-fill two culture tubes with A . Add l g alpha-amylase to tube 2 . After 30 min, project in H-3. Add a dropperful of B to each cell. Observations: Tube 1: deep iodine-blue showing presence of starch. Tube 2: pale hlue, showing starch has disappeared, the amylase fermenting it to sugar.
of Wood
Experiment dezleloped by August J . Colo. To show: Products from the distillation of wood. Materials: A 13 X 100 mm test tube quarterful of soft wood chips; one-hole rubber stopper carrying a l/a-inch copper delivery tube in through a 2-hole stopper in an empty 2-02 square glass bottle; an exit tube of glass or copper leading to a second 2-hole stopper in a 2-02 square glass bottle quarterful of dry CaO; an exit tube of copper or 5 mm glass tubing. Procedure: Project with the test tube of dry wood chips over an alcohol burner. Heat as hot as possible. I n a few minutes gas will issue from the exit tube in the end bottle, and can be ignited there. Hold a matchhead in this flame. Observations: Wood-tars collect in the empty bottle. I n the second bottle pyroligneous acids from the wood are absorbed by the lime. The exit gas burns and can be made visible on the projection screen by the match-head igniting. Note: Hard coal requires a much higher temperature than is provided by the alcohol burner. A634
/
Journal of Chemicol Educafion
Dern. 671-Titration
of Vitamin-C with Iodine
To show: Vitamin C content of orange juice treated with iodine and back-titrated with thiosulfate. kc-COH=COH-CH-CHOH-CHSOH + In O=C-COHI-COHI-CH-CHOH-H
-
Materials: Orange juice, 0.01 N iodine-aq, conc. HISO#,starch-a C-1, medicine droppers, 0.01 N sodium thiosulfate-aq, stirrer. Procedure: Project C-1 containing 30 ml of orange juice dropperful of starch-aq dropperful of conc. H2S04 (CAREin adding, make sure does not injure the plastic). Now titrate with iodine, (class counting drops), adding about 10 drops in excess. Back-titrate (class counting) with 0.01 N thiosulfate. Wash out cell a t once to prevent iodine stains.
+
+
Calculations: Milli-equivalent weight of vitamin C (ascorbic acid) is 0.088. One sample of orange juice had 0.7 mg ascorbic acid per ml of juice. Reference: (1947).
GILKEY,
w.
A.,
J. Chem. Educ., 24, 458
