LETTERS Cooperative Objective Tests in Organic Chemistry To the Editor: This will serve as a progress report on the work that has been done on this project, and as an invitation to others to cooperate. As an evidence of progress, over twelve hundred tests covering the first semester's work in organic chemistry have been distributed to instructors in forty-two difFile No.
ferent institutions. In addition to this, twenty-eight other institutions have asked to be supplied with copies of these tests. This is indicative of a rather general interest in this project, and we are hopeful that something of a very definite character may be accomplished. For the benefit of those who are not familiar with the use of objective examinations in organic chemistry, the following type test is submitted for careful consideration.
Acids, Substituted Acids, Acid Derivatives Namc
B y encircling the proper ~ubscriptrwhich appear beneath each item on the lcft, indicate the item or demr i n the group listed at thc right that apply with ilhrepcct to: A.
THE TYPE FORMULA OR FORMULAS
1
1
8
4
1
8
1
8
#
1
0
A hydroxy monoacid 1
1
I
,
L
8
,
8
,
,
4
0
5:
An acid halide B.
Formic acid 1
1
3
4
6
1
1
8
9
1
0
8
7
I
P
L
0
Maleic acid L
1
1
4
6
Octyl acetate I
l
l
,
&
l
l
l
S
R.C-0.X .. ... .
RC0.O.R
I
4
6
Lactic acid
1
1
1
4
8 1
1
I
~
D
7
1
t
O
9
Z
I
a
4
L
I
I
I
l
O
I
O
H0.0CCH2C0.0H L
~
I
~
S
I
T
I
O
L
O
CH&HOH.CO.OH I
Z
~
~
L
O
~
S
~
+
CHrCHrCO.OCHa 1
1
1
4
6
1
1
1
S
U
1. 1 1 1 e I 2. H,N.CH2.C0.0H -+HOCHrCOOH 3. ~ z i a s e i a s ~ o 4. 5. CHa.CO.OH + CHaCO0OCCH8 1
1
1
CH1.CP.:HL0
4
1
1
1
8
9
1
P. I
L
I
4
L
I
OF:
REAGENTS REQUIRED Distilled water HONO/(NaN02/H+), aq. Heat H2C:C:0 Distil
6. Succinic acid 7. 2-Hydraryprapanoic acid 8. Glutaric Bcid 9. Methyl etlianoate 10. Name not indicated FOR:
6.
T
8. PCIS 9. CHd20.0H/(P201) 10. Not indicated here IN:
2.
I
9
,
NaOH. aq.. heat
7. 2H2O/H+
1. HC1, dry
-+b
a I
Carrots -~~~~ ..-
10. Animal tissue
6. To re,mave iron rust 7. I n shoe polish 8. I n ~ e r k r n e s 9. I n h f t drinks 10. No use indicated
THE REAGENT REQUIRED POR EACH STEP
6
I
'
%
0
CHs.C0.?H6+p L
7. Tobacco 8. Nettles
OP:
D. T H E NAME OR NAMES 1. Malonic acid 2. Propanedioic acid 3. Methyl acetate I4. Lactic O acid 5. Pyruvic acid
THE REAGENT OR
E.
CHrCN
THE USE OR USES
1. I n infant foods 2. As a soap 3. In cosmetic creams 4. As a solvent 5 . I n baking powders
Sodium palmitate I
R.CO.O.OC-R C.H~+LCO,OH C,Hz,+-v(OH)vCO~OH C"Ht,-p(CO.OH)r Not mdmated
U
C. I
6. 7. 8. 9. 10.
THE OCCURRENCE OR OCCURRENCES OP: 1. Rhubarb 2. Ants 3. Berries. 4. Oranges 5. Peppermint
Stearic acid L
90R:
1. RCO,OH 2. HO.OC CH2C0.0H 3. C"Hm(C0 OH)*
An unsaturated monoacid
CI,/(S, light) 3. Cb, aq. 4. H.CN/(NHz) 5. H1Cr20v,aq.. heat
O
B +HO.OC.CHrCO.OH
6. N a C N 7. Na/CHrCHrOH 8. 2H10/H+ 9. Air/(AcO)zMn 10. Not indicated here
L I I . ' ' I I D , @
G.
THE
CHvCO.OH L
I
I
(
I
I
~
I
~
U
CHvCHOHCO.OH I
I
P
~
I
I
CHr.CO.O.CHrC& 1
1
1
4
1
*
1
I
,,
I
~
U
DESCRIPTION OR DESCRIPTIONS THAT APPLY: 1. Colorless liquid 2. Pleasant odor 3. Irritating odor 4. Water soluble 5. Sweet taste
6. 7. 8. 9. 10.
Ether soluble Sour taste Brown color Insoluble in water Viscous
CsH6 1
1
+ air/(V~Os.450°C.) -+
1
4
1
%
J
1
8
9
1
0
+ H C N + 2H2$/HC 4
CHs.CHO L
1
1
6
6
1
1
$
ZH.CO-ONa +heat, 200°C. I
,
i
.
R. THB PRODUCT OR PRODUCTS PORMED BY:
S
l
,
l
.
,
O
+ I.
CHrCO.OH 1
1
1
4
1
1
1
Q
S
I
O
2
8
4
L
I
7
I
1
1
0
~
CHrCO-O,CH~CH~ 1
1
l
4
r
l
l
8
.
1
1
1
1
1
1
1
1
1
1
K.
1. 2. 3. 4. 5.
I I , , ' I I I D , O
HOOC~C~OHCH,OHCOOH 2
6
8
8
9
1
0
CHsCO.OCHrCHa 1
1
1
4
1
1
1
1
1
6. 7. 8. 9. 10.
Maleic anhydride NaO.OCCO.ONa NCCHKHO H2 CHICHOHC!O.OH Not indicated here
6. 7. 8. 9. 10.
Halogenation/catalyst Reductionjcatalyst Addition Alcoholysis Ammonolysis
+
6. NH,, aq. 7. Cu++/(OH-). aq. 8. CHzCO.CI 9. NaHCO., heat 10. NaOH/(CaO). heat
T A R REAGENT OR REAGENTS TEAT WILL AID I N IDENTIPYIND:
HO.OC.CO.OH 9
Polymerization Burning, vapor phase Oxidation, mild Lactide formation Saponification
1. NaOH, aq. 2. PCb 3. CHvCH2.0H/H+
0
HOOC.CHOHCHOH.COOH
1
+
0
CHvCHyCO.OH 1
Suecinic anhydride Oxalic acid Lactic acid NaOH CaO HO-OCCO.OH
TYPE REACTION OR REACTIONS FOR:
1. 2. 3. 4. 5.
CHvCHOHCO.OH 1
1. 2. 3. 4. 5.
1
c. HISO,, heat KMn04/Hf. aq.. heat CuC+/OH-, aq. CaHs c. NHs/H1O, stand, distil
6. Ca(OH),, aq. 7. CH&HrOH 8. Heat 9. Distil (b. p.) 10. Not indicated here
0
TAB COXMERCIAL SYNTHESIS OR SYNTAESBS OF: " " " I'
" "
++ +
+
1. CHrCHO HCN 2HnO/HC+ 2. CaH* HzO/(Hgf+, HzSOI) air/(AcO),Mn + 3. CsHs air/(VnOi, 450PC.) H1O -+ 4. CHrCOCI Ns.0CH2.CHa-+ 5. CHrCO.OH H3C:C:O -+ 6. CO NaOH, 200°C. H f , aq. --+ 7. CxH, 2CHrCO.OH/(catalyst) heat + 8. CHI.CHZCO.OH CI2/(S) NaOH, aq. H+. aq. 9. CH&O.O.OC.CH, HIO/H+ -+ 10. H C H O Hl/(catalyst) -+ 11. H*C:CH* H,SO. HzO, distil -+ 12. CO H,/(catalyst), heat. pressure 4
+
+ +
+
+ + +
+ +
+
++
+ +
+
+
.. This examination, in the opinion of the writer, satisfies all of the normal requirements of a test as a measuring device. Twelve Werent approaches to a tapping of the student's knowledge are utilized, each of which may be rated according to its relative importance with respect to the topic covered. The qversity of choices, under each of the general divisions, practically eliminates guessing. Guessing, in an examination of this type, is especially disconcerting to the student if the test is rated on the basis of right minus wrong. A careful consideration of this test will indicate that it is not an examination in which the student returns, in a parrot-like manner, what he has heard in the classroom or read in his book. The organization is diierent, and a set of thonght-provoking possibilities present themselves. The student is required to think, and think accurately. The "spoon-fed student" becomes lost in amaze of uncertainties. A slight modification of this test, in which a special answer sheet is used, makes it possible to rate this type of test by the new automatic grading machines that are now available in certain institutions. In one such test, two hundred thirty papers were accurately scaled on the basis of right minus wrong in just seventy-eight minutes. Since there were ninety-six items on each paper,
:.
this meant grading twenty-two thousand eighty items. What an economy of time and energy on the part of the instructor that may now be expended in the fonn of more constructive work! Any who are interested in cboperating on this project should contact the writer.
The Hare a n d the Horse T o the Editm:
It is not inevitably obvious that H I means one part (0.8 per cent) of hydrogen and 127 parts (99.2 per cent) of iodine, and not one part of hydrogen and one part of iodine. Hence the suitability of the Fable of the Hare and the Horse. Once upon a time a voyager in a far land desired rabbit stew. When i t arrived he demanded if it contained horse meat. "But yes," replied the garson, "half-and-half, one rabbit and one horse." E. A. VUILLEUMIER DICKINSON COLLEGE
CARLISLE, PENNSYLVANIA
