F. M. Van Meter and W. H. Eberhardt Georgia Institute of Technology Atlanta, Georgio, 30332
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Textbook Errors Index
It has been twelve years since Professor Karol Mysels introduced the Textbook Error Column OF CHEMICAL EDUCATION and many topics have been treated in this mlumn. It to the JOURNAL is probable that authors, teaxhers, and students have begun to lose track of these columns and many of the errors persist. Therefore, this Index has been assembled in an sttempt to call attention to all of the contributions which have appeared since the initiation of this column and, where we sre aware of them, to letters and other papers which are relevant. Textbook Error 1 appeared in April 1955; coverage here includes Number 72 from the December 1966 issue. Obviously, complete literature searches on all these topics is far beyond the scope of this Index and we make no claims for completeness in finding letters and other appropriate articles. The series will continue as long as appropriate material is available. Contributions should be sent to Professor W. H. Eberhardt at the Georgia. Institute of Technology. We anticipate bringing this Index up to date periodically and would appreciate suggestions from readers as to references which OF CEEMICAL EDUCATION should be included in future versions. All references are to the JOURNAL unless indicated otherwise. 1. The Mechanism of Vapor Pressure Lowering, MYSELS,K. J., 32, 179 (1955). Restriction of the rate of evaporation by solvent molecules in the surface of a solution has been used to explain Raoult's Law. This explanation is shown to be incorrect. See also BRESCIA. F. 2. Brownian Motion and the Stability of Colloids, MYSELS,K. J., 32, 319 (1955). Brownian motion can account for the stability of only the smallest collodial dispersions. For larger particle siaes, thermal convection currents and slow rates of sedimentation are controlling factors.
3. The Solubility of Gases in Liquids, MYSELS,K. J., 32, 399 (1955). It is usually thought that increasing the temperature decreases the solubility of a gas in a liquid. This has been found to he untrue in a, number of systems. 4. The Sensitivity Change of Analytical Balances, MYSELS,K. J., 32, 518 (1955). Bending of the beam is thought to be the most important factor in determining the change of sensitivity with load of an analytical balance. Beam bending. however. is shown to have a. negligible effect on the sensitivity under'normal conditions. 5. The Reaction of t.he 1.erlnnehP -Dm ~-~~ - " Cell - - ~ ~ a MYSELS,K. J., 32, 638 (1955). The role of the MnO? in the Leclancbh dry cell is not simply to scavenge the hydrogen produced s t the mode. The emf for reduction of the MnOl makes a contribution to the total emf of the cell, and ZnMn901is an important end product. ~
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6. The Formula of Cuprous Compounds, MYSELS,K. J., 33, 86 (1956). The existence of Cu?+ ion, inferred from the known Hg2+ ion, is doubtful. There is no evidence to support dimeriaation or 8. Cu-Cu bond in Cu(1) compounds. 7. The Laws of Reaction Rates and of Equilihrium, MYSELS,K. J., 33, 178 (1956). The form of an equilibrium constant is often derived from rate laws based on the overall reaction equation. These rate laws often do not reflect the actual reaction mechanism but the derivation is still valid since the position of equilibrium does not depend on the mechanism of reaction.
8. The Definition of Transference Numbers in Solution, SPIRO,M., 33, 464 (1956). The common definition of transference numbem in terms of fraction of total current has rtn operational meaning only in simplest systems. The advantage of an operational definition in terms of ion constituents is discussed.
356 / Journal o f Chemicol Education
9. More About the Laws of Reactions Rates and of Equilibrium E. A., 33, 544 (1956). GUGGENHEIM, The kinetic behavior of a reaction cannot be predicted from the stoichiometry of the reaction; it must be determined experimentally. Guldberg and Waage were not the first to note the relationship between the quantitative expression for the equilihrium constant and the stoichiometric reaction equation. See also BEESCIA,F., 34, 155 (1957); LUND,E. W., 42,548 (1965). 10. The Classification of Crystals, MYSELS,K. J., 34, 40 (1957). The classification of crystals into crystal systems on the basis of the leneth and direction of the crvstal axes can lead to errors. The svmmetrv of the ervstd in all of itenronnrties must confirm
11. The Production of Mercury, PERETTI,E. A., 34, 135 (1957). In the production of mercury from HgS by retorting high-grade ores. CaO is used to mevent the recombination of mercurv and 4 S = 3 CaS c~SO~, sulfth by the reaction: 4 CaO
+
+
This Index has been prepwed under the sponsorship of the Advisory Council on College Chemistry. The Advisory Council is supported by the National Science Foundation. Professor L. Carroll King, of Northwestern University, is the chairman. Single copy reprints of this paper are being sent to chemistry department chairmen of every US. institution offering college chemistry courses and to others on the mailing list for the AC3 Newsletter. Additional single copies will be sent free to all interested individuals who make request to: Advisory Council on College Chemistry Department of Chemistry Stanford University Stanford, California. 94305 For class use, multiple copy orders (in lots of 10) can be filled if accompanied by remittance of $1.50 per tmit of 10 copies. No order can be billed. Cheeks should be drawn to the order of the Advisory Council an College Chemistry. Orders must be addre8sed lo AC8, not to the Journal o j Chemical Education. This is Serial Publication No. 25 of the Advisorv Council.
The srnrcmcnt that the derantpwition tempcrarurcs of the alkali nitrate.; arr low a n d tlrnt the amcspmding ~itrircqcqn he prepared easily is in error. Conductivity measurements are used often to determine the structure of complexes. To do this, one must clearly understand the difference between equivalent and molar conductance. Molecular weight is a dimensionless number whereas gram molecular weight denotes an amount of material equal to that dimensionless number.
12. The Lubrication Properties of Graphite, L A ~ R A V., ~34, , 240 (1957). The low friction and wear of graphite surfaces are due to the presence of adsorbed gases or vapors and not to the laminar structure of graphite. 13. The Nature of Ionic and Molecular Species in Sulfuric Acid, BRUBAKER, C. H., JR., 34,325 (1957). Sulfuric acid may he thought to he relatively weak due to the small second ionization constant. Actually, the acid strength of concentrated sulfuric acid is comparable with perchloric acid. 14. Arsenic(V) Chloride, DASENT.W. E.. 34. 535 (1957). There is nu evidrlwe 10 syqmrt tlre r x i ~ r e ~ufw arscvllr.\) I l l . S m e eleu~wrrtsuf the firat lung perld of thc I'eriodir Tablcaw mted tu be rrlurrn~~r runsumc rheir h i g h ~ Pt X ~ C C W covalences.
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15. Miscellanea: The Solubility of Acetates; The Effect of Light on Reactions. . \ I Y ~ E L ~ , J., K . 35, 32 (1038). ?\rcrstc $:,115, ~houghtII Iway~to be O I U ~ I Pi n water, slmw numy tusratm.. ui I m solubiity. I.~ght r ~ n r w be t rhuughr to act RS a e a t ~ l p tin photurhewirnl martions smcc i t i s ronsumd in the roorvr of tllr rpavtimarid it shifts the position of equilibrium ~~
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16. The Vapor Pressure of Hydrated Cupric Sulfate, LOGAN, T. S., 35, 148 (1958). The system cupric sulfate-water is frequently used to illustrate phase equilibria. The data generally quoted is not in agreement with the most reliable values reported, particularly for the CuS0..H20-CuSOn equilibrium. 17. The Meaning of Mole Frsction, 3. M., AND PEERDEMAN, A. F., 35, 240 (1958). BIJVOET, The mole fraction of a solute is a function of the molecular weight of the solvent; however, this molecular weight need never be that of the associating liquid but is either arbitrary or hss to be that of the vapor phase. 18. The Solubility Product Constants of the Metallic Sulfides, W. H., 35, 339 (1958). WAGGONER, Indirect methods for determination of solubilitv Droduet con-
fides are cited as often being unreliable. 19. The Relative Reactivity of Acetylenes and Olefins Toward Bromine, 35, 444 (1958). DANIELS,RALPH,AND BAUER,LUDWIG, It often is stated that bromine is more reactive toward alkynes than toward olefins. Alkynes have been found by experiment to react more slowly with bromine than alefins with similar structures. Evidence suggests that a free radical mechanism is important for the addition of bromine to alkynes. 20. Miscellanea No. 2: The Mesnine of Element: The Solubilitv of Phenol in Carbonate solutGns; The change of Vap& Pressure With Temperature; MYSELS,K. J., 35, 568 (1958). Confusion often exists in distinguishing between the terms "element" and "elementary substance." Contrary to some texts, phenol is soluble in sodium carbonate solution. heine a stronger acid than the bicarbonate ion. In disc&singthe change of vapor pressure with temperature, the effects of the molar volume of the liquid and the total externa.1 pressure often are ignored.
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23. Atomic Masses, Binding Energies, and Isobaric Stability, POE,A. J., 37, 92 (1960). Increase in binding energy is usually given as a criterion of spontaneity in a nuclear reaction. This is correct in certain cases, e.g., a-decay and fission, but incorrect for isobaric decay (@-emissionand electron capture). The basic criterion of spontaneity is that there should be a decrease in mass in the reaction. 24. The Fehling and Benedict Tests, DANIELS,R., RUSH, C. C., AND BAUER,L., 37, 205 (1960). Use of the Fehling and Benedict tests to detect simple aliphatic aldehydesisnot valid; a-hydroxyaldehydes, a-hydroxy ketones and u-ketoaldehydes reduce the Cu(I1) ion, other ketones and D. A. H., 38, 102 (1961). aldehydes do not. See also TAYLOR, 25. The Sidechain Halogenation of n-akyl Benzenes, GOLDWHITE, H., 37, 295 (1960). I t is frequently stated that there is a strong tendency for halogenation to occur a t the carbon stom next to an aromatic nucleus. I n fact these reactions are sensitive to the reaction conditions and isomer mixtures often occur, especially at high temperatures. 26. Solubility of Gold in Mercury, BROWN, J . B., 37, 415 (1960). Many chemists have the impression that gold is rather soluble in mercury. However, gold is not very soluble in mercury, and the amalgamation process far gold recovery depends on the wetting of gold by the mercury and not the solubility of gold in mercury. 27. The Criterion for Optical Isomerism TKOMPSON, H. B., 37, 530 (1960). Lack of s. olane of svmmetrv has been used as a criterion of
involving reflection. 28. The Shape of the 2p and Related Orbitals, 38, 20 (1961). COHEN,IRVING, The shape of a 2p orbital is often represented by a graph of the angular part of the 2p wave function. To show the true shape of an orbital, the total wave function must be used. 29. The Existence of Endothermic Adsorption, J. M., 38, 138 (1961). THOMAS, I t is often thought that all adsorption processes are exothermic. Certain ohemisorptions, however, are endothermic due tu a H. H. G., 38, 378 positive entropy change. See also JELLINEK, (1961). 30. The Ioniaat,ion Constant of Water, DIRKJE,T. P., 38, 260 (1961). I n formulating the ionization constant of water, the aeGvity of the water is usually ignored. This can lead to appreciable errors in calculations involving concentrated solutions.
21. Weathering Reactions, Y A A L ~ D. N , H., 36, 73 (1959). Insufficient regard is frequently given to complex weathering nrtctions. The weathering mechanism can be generaliaed to: aluminum silicate material and water give ions and amorphous intermediate products which give clay and soluble salts.
31. The Pyrolytic Decomposition of Carboxylate Salts to Ketones, J. P., 38, 300 (1961). SCHULTZ, H. P. AND SICHELS, Pyrolysis of calcium and barium carboxylates has heen stated to be a general method for preparation of ketones. In practice complex mixtures usually occur and the ketone is often only formed in low yield. See also Slarra, W . B., 38, 638 (1961); FLANAGAN, P. J., 39,593 (1962).
22. Miscellanea No. 3: Thermal Decomposition of Alkali Nitrates; The Conductivity of Complexes; Gram Molecular Weight, MYSELS,K. J., 36, 303 (1959).
32. The Equilibria of Complex Formation, BANKS,J. E., 38. 391 (1961). The intermediate species in the formiltion of a complex ion are frequently ignored in cdculations involving the formatiou con-
Volume 44, Number 6, June 1967
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stant of the ion. This can lead to serious errors when the wncentrations of the intermediate species are not negligible. 33. The Paddle-Wheel Crookes Tube, J . A., 38, 480 (1961). CAMPBELL, In the paddlewheel Crookes tube the paddle wheel does not move h e c a w of the momentum of the electrons striking it. radiometer. 34. Dipole Moments of Symmetrical Organic Molecules, W. N., 38,522 (1961). MOULTON, Some classes of compounds, such as symmetrical t~ans-olefins and pawAsuhstituted benzenes are said to have a zero dipole moment by symmetry. If the sttached groups themselves are sufficiently unsymmetrical, the molecule need not possess a center of symmetry, and hence, may have a finite dipole ~ , AND Dows, D. A., 39, 480 moment. See also D o ~ o a u J., (1962). 35. Miscellanea No. 4: The Chromyl Chloride Test for Chlorides; L'Monovalent" Oxygen Compounds; Ternary Diagrams, MYSELS,K. J., 38, 627 (1961). Iodine or bromine may interfere with the chramyl chloride test for chloride. Compounds based on 9-oxyanthracene have been mistakenly thought to he examples of stable oxygen free radicals. Three-phase regions an ternary diagrams are frequently mislabeled as two-phase regions. 36. Flow of Glass Under its Own Weight, DINQLEDY, DAvm, 39, 84 (1962). Glass does not Row measurably a t room temperature as a viswrm liquid under stress but does accept s non-permanent deformation, returning to its original shape slowly after the stress is removed. This deformation may he mistaken for viscous Raw. 37. The Aoylstion of Aliphatic Unsaturated Hydrocarbons, J . G., 39, 206 (1962). SHAREPKIN, The acylation reactions of aliphatic compounds are often neglected in the diseussion of acylation reactions. 38. Energy Level Diagrams and Extranuclear Building of the Elements, KELLER,R. N., 39, 289 (1962). A relative order of stability of atomic orbitals is usually stated. The order of stability will often change with changes in the nuclear charge or number of electrons surrounding the atom. 39. The Configuration of (-)-Shikimic Acid and Certain Biochemically Related Compounds, K. R., 39,419 (1962). HANSON, The structure of biochemically active shikimic, 5dehydroshikimic, &phosphoshikimic, quinic, and 5dehydroquinic acids are frequently mistakenly represented by their mirror images.
43. The Deoarhaxylation of Organic Acids, Mmca, JERRY,40,212 (1963). Some texts l i t decarhoxylatian of an organic acid or salt as a general method for preparation of dkanes. Simple aliphatic acids, except acetic, do not give good yields on decssboxylation, and mixtures of alkanes occur.
44. Friedel-Crafts Akylation, MARSI,K. L., AND WILEN,S. H., 40, 214 (1963). Friedel-Crafts alkylations are usully discussed only in terms of anelectrophilic mechanism. Appearance of large percentages of n-akyhted products in some case's suggests a competing nucleophilic displacement mechanism. 45. Catalytic Inhibition by Adsorbed Hydrogen, S. R., 40, 473 (1963). LOGAN, Catalytic inhibition of the dewmpositian of ammonia an n catalyst by hydrogen has been found to occur by a more wmplex mechanism than simply occupation of the active sites on the catalyst by the hydrogen. 46. Deviation from Raault's Law, MCGLASHAN, M. L., 40, 516 (1963). It is frequently assumed that deviations from Rmolt's Law must he always either positive or negative for s h i w y mixture. There is no thermodynamic restriction of this sort and examples where deviations change sign are known. 47. On Hydrogen Bonds, Do~oauE,JERRY,40,598 (1963). I n discussing hydrogen bonding, geometric restrictions on the bond angles and the steric effect of the hydrogen are often neglected. This may lead the student to inwrrect wnclusians about the structure of compounds. 48. The Direct EsterScation of Phenols, OFFENHAUER, R. D., 41, 39 (1964). Contrary to ststement~in some texts, it is often possible to esterify phenols directly with carhoxylic acids. 49. Work of Comp~essingan Ideal Gas, BAUMAN, R. P., 41, 102 (1964). Perfect gas wmpression problems often wntain no explicit statement of revemibility. This leaves the student uncertain how to calculate the work done by the gas. Since work is not a state function, the exact path must he specified by which the process occurs in order to calculete the work. See also CHESICK, J . P., 41, 674 (1964); B ~ M A N R.,, 41, 675 (1964); KOKES, R., 41, 676 (1964); MYSELS, R. J., 41, 675 (1964); BAUMAN, I., and KIVEI^SON, D., 43, K . J . , 41, 677 (1964); OPPENHEIM, 233 (166). 50. Limitation of the Hillsberg Method for Primary Amines FANTA,P. E. AND WANG, C. S., 41, 280 (1964). Solubility of the bewensulfonamide in alkaline solution has been stated to be a certain test for primary amines (Hinsberg test). A number of primary amines me known to give insoluble benzensulfonamides, particularly cycloalkylamines. See also S~CKLER, W. C., 41, 515 (1964); GENNARO, A. R., 42, 48 (1965).
40. Deriving the Gibbe-Duhem Equation, ROGERS, D. W., 39,527 (1962). Assumption of wnstsnt partial molar properties in the derivation of the Gihhs-Duhem equation leads to an invalid result. Use of Euler's theorem gives the equation in a rigorous manner. See also CONDON, F. F., GILMONT,ROGER,LORIMER, J. W., I. H. AND ROGERS, DONALD W., 40, MISSEN,R. W., SPINNER, 225 (1963).
51. Evidence far the Configuration an Carbon 1 of D-Glucose, J. P., AND SCHULTZ, H. P., 41, 343 (1964). SICKELS, The conductivity of boric acid solutions wntaining glucose is used to assign the wnliguration on carhon-1. This argument was based on a furanose structue while glucose is now known to exist in a pyranose stmcture for which the argument is invalid.
41. The Thermal Dewmpasition of KCIOs, K., AND HANSEN,K. O., 39, BOSTWP,O., DEMANDT, 573 (1962). Thermal decomposition of potassium chlorate catalyzed by manganese dioxide is quoted often as a convenient source of oxygen. Chlorine wntaining gases such as Clz and Cl01 also are formed.
52. The Decolorization of Baeyer's Reagent by Primary and Sewndsry Alkanols, J . S., 41, 392 (1964). SWINEHART, Primary and secondary alcohols are often said to dewladze neutral dilute aqueous potassium permangrtnste (Baeyer's reagent). This is fonnd generally t,o he untrue for saturated alwhols.
42. The Thermal Stability of H&, HAYES,K. E., AND H-USE, N. R. M., 40,149 (1963). H,Se is often stated to be thermally unstable. Experiments show that H2Se is stable a t least to 280°C although mixtures of HSe and air are readily dewmposed a t this temperature.
53. Systematic Names for the Tartaric Acids, BAXTER,J. N., 41, 619 (1964). The tartaric acids me often named D-tartaric acid or rctartwic acid without referenee to whether the carbohydrate (Rosanoff) or amino acid systems iu being wed. The diierence lies in
358 / lournol of Chemical Educofion
whether the absolute configuratiun of the lowest numbered or highest numbered asymmetrio earhon is taken ken the basis for the nomenclature. 54. Chemical Pote~itialsin an Ideal Mixture of Ideal Gases, ROBINSON, P. J., 41, 654 (1964). I n a common derivation of the chemical potential for an ideal gas mixture two errors in differentiation cancel and lead to the correct result. 55. Photochemistry: Threshold Frequencies and Temperature Dependence of Primary Processes, INNES, K. K., 42, 109 (1965). The statements that definite photoehemiml threshold frequencies exist and that photochemical activrttion s t a single wavelength is independent of temperature are refuted. 56. Dewloriaittion of Glass, DINGLWY,DAVID,42, 160 (1965). In the decalorisation of glkens, MnOn does not oxidize Fe(I1) to Fe(II1) hut acts as a physical dewloriaer, masking the bluegreen color of Fe(I1) by addition of a complementary red wlor.
66. o-Nitrohenzaldehyde and the Bensoin Condensation, S ~ C K E LR. , F., OPPELT,J. C., .WD ARENDT,V., 43, 144 il9fifil. ~-~..,. It is usually stated that o-nitrobenaaldehyde undergoes the benzoin condensation whereas p-nitrabenzddehyde does not. This is said to he due to steric effects preventing the nitro group from acting ken an electron withdrawing group in the o-nitrohenzaldehyde. This assertion is based on the observation of 2,2'-dinitrobend as a reaction product. The product identified as 2.2'dinitrobeneil bas been shown not to be 2.2'-dinitrobenzil, and it has been shown that no 2,~'-diniimbensil is formed in the reaction. ~~
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67. Raoult's Law and the Thermodynamic Definition of Ideal Mixing, WILLIAMSON, A. G., 43, 211 (1966). Raoult's law and the thermodynamic definition of ideal mixing are usuallv said to be eauiv&nt if the vaoors behave as ideal gases. his is shown to be untrue, the error arising from neglect of the effect of pressure on the chemical potential of the liquid phase.
57. The Oxygen Coordinations of Lithium, J. W., 42, 223 (1965). DONNAY, G., AND GRYDER, Lithium, usually thought to he only tetrahedrally coordinated by oxygen, has octahedral oxygen coordination in several minerals and in the nitrate and iodate.
68. The Activating Effect of Fluorine in Electrophilie Aromatic Substitution, AULT,ADDISON, 43, 329 (1966). Halogens are generalized to be ortb-pam directing and deactivating in electrophilic aromatic substitutions. Fluorine is found, however, to activate the position para to it.
58. Crystal Field Splitting Diagrams, J. J., 42, 315 (1965), ZUCKERMAN, The ratios of energy terms for ligand-metal ion attraction, ligandd-electron repulsion and d-orbital splitting by the crystal field are frequently inadequately emphasized. Electronelectron repulsions in the d-~rhitalsare usually ignored. See J. J.,42,688 ~ISONOKBURY, A. H.,42,688 (1965); ZUCKERMAN, (1965). . .
69. Kinetic Theory, Temperature, and Equilibrium, D. K., 43, 332 (1966). CARPENTER, Several texts maintain that an essential postulate of the kinetic theory of gases is that the mean molecular kinetic energy is proportiand to the absolute temperature. This statement is valid as a wnclusion of the molecular kinetics but is not necessary as a postulate
59. The Original Observations of Brownian Motion, L ~ Y ~DATID, N , 42, 367 (1965). Brown did not observe the motion of pollen grains in suspension. The particles for which the motion was observed were from within the pollen grains, probably cytoplasmic granules.
70. Light Absorption in Photochemistry, SHAW,HENRY,AND TOBY,SIDNEY,43,408 (1966). Many photochemistry texts ignore some of the basic physics of light absorption. A development of the Beer-Lambert relation from Maxwell's equations is given and photoinitisted processes are discussed.
60. QUALIT.~T~VE TEBTSfor Kt, McCoy, R. E., 42, 444 (1965). When the flame test is used as a confirmstory test for potassium in wbaltinitrite precipitate, the cobalt is found to interfere. The cohaltinitrite precipitate test also is of questionable value. 61. Reversible Work, 8. D., 42, 547 (1965). CHRI~TIAN, Ouly for isothermal processes is reversible work always greater than irreversible work. The restriction of constant temperature is often ignored. 6'2. The Difference Between C , and C, for Liquids and Solids, SXTH, N. O., 42, 654 (1965). The difference between C, and C , for condensed phases is osuslly dismissed as negligible. In some cases this isnot true, fur example in CS2, . C ., is 35% .. lamer - than C..
(i3. Kinetic Energies of Gas Molecules, ~ E R N E J. , C., 42, 655 (1965). Some texts show kinetic energy d i s t r i b u t i o ~of gas molecules with points of idection on both sides of the maximum in the curve. There should be no infleotion on the low energy side of the maximum. 64. Permanganate Hydroxylation of Alkenes, SNYDER, C. H.,43, 141 (1966). Texh often cite neutral potassium permanganate as a reagent for conversion of alkenes to cis-glycols. Usually, alkaline permanganate is a, distinctly superior reagent for this oxidation aud neutral permanganate produces oxidation to ketols or cleavage to aldehydes. 65. The Coupling of Diasoniom Salts, FNGERIO,N. A,, 43, 142 (1966). Several diazo conpling generalirstions are not valid, among them the impracticability of all diazo cauulina in acid medh. intermedia& the concept of the diazo-hydroxide a8 a r&&e and the assertion that the syn-diazotate couples whereas the antidiazotate doe3 not.
71. Cosmic Rays, ALLEN,WILLIAMF., 43, 592 (1966). A very common misapprehension among chemists is that cosmic rays are high frequency electromagnetic radiations from interstellar space. Although yrays are produced in cosmic ray showers, most cosmic rays are fasbmoving charged particles. 72. Substitution Reactions in Octahedral Complexes, JONES,G. R. H., 43, 657 (1966). It is repeatedly stated in texts that all ndeophilic substitution reactions of octahedral complexes go - via an aauo w m ~ l e xin aqueous solution. A number of reactions, however, have been found to go by direct substitution.
Textbook Errors Discussed Elsewhere A number of textbook errors have been discuased elsewhere in sufficientdetail to make s. full resenta at ion in the Textbook Error
1SDE. Le Be1 and Tetrzhedral Carbon, SEMENTSOV, A., Am. Scientist, 43, 97 (1955). Many textbooks oredit Le Bel (along with van't Hoff) with originating the tetrahedral theory while in fact both introduced the concept of the unsymmetrical carbon atom, but Le Be1 for a long time opposed the tetrahedral model and even tried to disprove it experimentally. 15DE. The Production of Aluminum, HENDRICKS, B. C., J. CHEM.EDUC.,32, 97 (1955). Cryolite is consumed significantly in the Hall process with important economic and air pollution consequences. 15DE. F ~ ~ m a rAcid. ie PATTON,A. R., Chem. Eng. News, 33, 3147 (1955). Many hiochemicd texts erroneously give a cis formula for fumaric acid which in reality is the t r a m isomer of maleic acid. Volume 44, Number 6, June 1967
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20DE . The Action of Phosphorus Pentachloride on Ether. J., AND BARNETP.E DE BARRY.S c h l ZUSSMAN. Sci . Reu., 37. 271 (1957) Evidence for the formation of alkyl chloride and phosphoryl chloride by this reaction indicates that no such reaction ooeu~-8 but that an error probably dipped into a translation about a hundred years ago See also B a n ~ ~ rEr .. DE BARRY.35. 636 (1958)
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Teleology. BERNATOWICZ. A J., Science. 128. 1402 (1958).
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