COVERAGE OF INTERMOLECULAR FORCES IN ORGANIC CHEMISTRY TEXTBOOKS

Silva Júnior, José Nunes da; Oliveira, José Mariano de Sousa; Alexandre, Francisco Serra Oliveira; Leite Junior, Antonio José Mello

doi:10.21577/0100-4042.20170766

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Educação • Quim. Nova 44 (08) • 2021 • https://doi.org/10.21577/0100-4042.20170766 copy

COVERAGE OF INTERMOLECULAR FORCES IN ORGANIC CHEMISTRY TEXTBOOKS

Authorship SCIMAGO INSTITUTIONS RANKINGS

The paper analyzes fifteen organic chemistry textbooks commonly used in Brazilian universities to examine intermolecular forces’ coverage in them. The findings revealed that the intermolecular forces are spread over a few pages (less than 1%) in a fragmented way, and over several chapters that do not provide enough information to help create a clear image in the student’s mind. Thirteen textbooks contained end-of-chapter problems related to intermolecular forces. However, less than 1.3% of the total (212) are associated with intermolecular forces. This deficient approach to intermolecular forces in Organic textbooks can lead to teachers’ lack of interest in teaching the subject, leading to students failing to learn this important organic chemistry topic.

Keywords:
intermolecular forces; organic chemistry; textbooks

Rating	Brazilian (%) (N =111)	French (%) (N =20)
Excellent	1.80	0.00
Good	31.53	20.00
Average	51.35	50.00
Bad	13.51	25.00
Awful	1.81	5.00

Author	Publisher	Edition	Total Pages	Total Problems	IMFs Pages^a a Number of pages related to IMFs b Number of topics related to IMFs cNumber of chapters covering any topic related to the IMFs dNumber of problems related to the IMFs.	IMFs Topics^b a Number of pages related to IMFs b Number of topics related to IMFs cNumber of chapters covering any topic related to the IMFs dNumber of problems related to the IMFs.	IMFs Chapters^c a Number of pages related to IMFs b Number of topics related to IMFs cNumber of chapters covering any topic related to the IMFs dNumber of problems related to the IMFs.	IMFs Problems^d a Number of pages related to IMFs b Number of topics related to IMFs cNumber of chapters covering any topic related to the IMFs dNumber of problems related to the IMFs.
Brown, W. H.²¹21 Brown, W. H.; Iverson, B. L.; Anslyn, E.; Foote, C. S.; Organic Chemistry, 6th ed.; Cengage Learning: Boston, 2012.	Cengage	6^th	1194	1463	14	9	12	44
Bruice, P. Y.²²22 Bruice, P. Y.; Organic Chemistry, 7th ed.; Pearson: New York, 2014.	Pearson	7^th	1293	1918	14	11	6	21
Carey, F. A.²³23 Carey, F.; Giuliano, R.; Allison, N. T.; Bane, S. L.; Organic Chemistry, 7th ed.; McGraw-Hill: New York, 2008.	McGraw-Hill	7^th	1229	1435	17	7	12	09
Clayden, J.²⁴24 Clayden, J.; Warren, S.; Greeves, N; Wothers, P.; Organic Chemistry, 1st ed.; Oxford University Press Inc.: New York, 2001.	Oxford	1^st	1512	585	7	5	5	00
Hoffmann, R. V.²⁵25 Hoffmann, R. V.; Organic Chemistry. An Intermediate, 2nd ed.; Wiley: Hoboken, 2004.	Wiley	2^nd	476	94	1	1	1	00
Jones Jr., M.²⁶26 Jones, M.; Fleming, S. A.; Organic Chemistry, 4th ed.; W. W. Norton & Company: New York, 2010.	W. W. Norton	4^nd	1220	1467	3	3	1	04
Klein, D.²⁷27 Klein, D.; Organic Chemistry, 3rd ed.; Wiley: Hoboken, 2016.	Wiley	1^st	1295	1895	11	6	2	11
Loundon, G. M.²⁸28 London, M.; Parise, J. Organic Chemistry, 6th ed.; W. H. Freeman and Company: New York, 2016.	W. H. Freeman	6^th	1485	1837	28	5	2	32
McMurry, J.²⁹29 McMurry, J. E.; Organic Chemistry, 8th ed.; Cengage Learning: Boston, 2012.	Cengage	8^th	1262	1842	5	4	3	03
McMurry, J.³⁰30 McMurry, J. E.; Organic Chemistry Biological Applications, 2nd ed.; Cengage Learning: Boston, 2011.	Cengage	2^nd	1044	1384	5	6	3	03
Smith, J. G.³¹31 Smith, J. G.; Organic Chemistry, 3rd ed.; McGraw-Hill: New York, 2008.	McGraw-Hill	3^rd	1178	2149	25	14	8	51
Solomons, T. W. G.³²32 Solomons, T. W. G.; Fryhle, C. B.; Snyder, S. A.; Organic Chemistry, 10th ed.; Wiley: Hoboken, 2011.	Wiley	10^th	1164	1266	9	9	1	12
Stowell, J. C.³³33 Fabirkiewicz, A. M.; Stowell, J. C.; Intermediate Organic Chemistry, 3rd ed.; Wiley: Hoboken, 2016.	Wiley	3^rd	335	230	1	1	1	01
Vollhardt, P.³⁴34 Vollhardt, K. Peter C.; Organic Chemistry: Structure and Function, 6th ed.; W. H. Freeman and Company: New York, 2011.	W. H. Freeman	6^th	1270	1702	14	8	9	06
Wade Jr., L. G.³⁵35 Wade, L. G.; Simek, J. W.; Organic Chemistry, 6th ed.; Pearson: New York, 2006.	Pearson	6^th	1262	1417	14	4	6	15

Category	Topics	Textbooks
Category	Topics	Brown²¹21 Brown, W. H.; Iverson, B. L.; Anslyn, E.; Foote, C. S.; Organic Chemistry, 6th ed.; Cengage Learning: Boston, 2012.	Bruice²²22 Bruice, P. Y.; Organic Chemistry, 7th ed.; Pearson: New York, 2014.	Carey²³23 Carey, F.; Giuliano, R.; Allison, N. T.; Bane, S. L.; Organic Chemistry, 7th ed.; McGraw-Hill: New York, 2008.	Clayden²⁴24 Clayden, J.; Warren, S.; Greeves, N; Wothers, P.; Organic Chemistry, 1st ed.; Oxford University Press Inc.: New York, 2001.	Hoffmann²⁵25 Hoffmann, R. V.; Organic Chemistry. An Intermediate, 2nd ed.; Wiley: Hoboken, 2004.	Jones Jr.²⁶26 Jones, M.; Fleming, S. A.; Organic Chemistry, 4th ed.; W. W. Norton & Company: New York, 2010.	Klein²⁷27 Klein, D.; Organic Chemistry, 3rd ed.; Wiley: Hoboken, 2016.	Loundon²⁸28 London, M.; Parise, J. Organic Chemistry, 6th ed.; W. H. Freeman and Company: New York, 2016.	McMurry²⁹29 McMurry, J. E.; Organic Chemistry, 8th ed.; Cengage Learning: Boston, 2012.	McMurry³⁰30 McMurry, J. E.; Organic Chemistry Biological Applications, 2nd ed.; Cengage Learning: Boston, 2011.	Smith³¹31 Smith, J. G.; Organic Chemistry, 3rd ed.; McGraw-Hill: New York, 2008.	Solomons³²32 Solomons, T. W. G.; Fryhle, C. B.; Snyder, S. A.; Organic Chemistry, 10th ed.; Wiley: Hoboken, 2011.	Stowell³³33 Fabirkiewicz, A. M.; Stowell, J. C.; Intermediate Organic Chemistry, 3rd ed.; Wiley: Hoboken, 2016.	Vollhard³⁴34 Vollhardt, K. Peter C.; Organic Chemistry: Structure and Function, 6th ed.; W. H. Freeman and Company: New York, 2011.	Wade Jr.³⁵35 Wade, L. G.; Simek, J. W.; Organic Chemistry, 6th ed.; Pearson: New York, 2006.
Types	London forces	A	A	A	0	0	A	A	A	A	A	A	A	0	A	A
	Dipole-dipole	A	A	A	0	0	B	A	A	A	A	A	A	0	A	A
	Hydrogen bonding	A	A	A	A	B	A	A	A	A	A	A	A	B	A	A
	Dipole-induced dipole	0	0	A	0	0	0	0	B	0	0	0	0	0	0	0
	Ion–dipole	B	A	A	B	B	B	B	A	B	0	A	A	B	A	B
	Ion-induced dipole	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0
Physical proprieties	Boiling point	A	A	A	B	B	A	A	A	A	A	A	A	0	A	A
	Melting point	A	A	A	B	B	A	A	A	A	A	A	A	0	A	A
	Solubility	A	A	A	B	B	A	A	A	A	B	A	A	B	A	A
	Density	A	0	B	0	0	B	0	A	B	0	A	A	0	A	A
	Meniscus and drop format	0	0	0	0	0	0	0	0	0	0	0	0	0	0	A
	Vapour pressure	B	0	0	0	B	0	0	0	0	0	0	0	0	B	0
	Dyes and dyeing	B	0	0	B	0	0	0	B	0	0	A	A	0	B	B
	Salting-out effect	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0
	Surface tension	0	0	0	0	0	0	0	B	0	0	0	0	0	B	0
	Adhesion-cohesion	0	0	0	0	0	0	0	0	0	0	0	0	0	0	0
	Capilarity	0	B	0	0	0	0	0	0	0	0	0	0	0	0	0
	Viscosity	B	0	0	0	0	0	0	0	0	0	0	0	0	0	B
Biomolecules	Cellulose and Starch	A	A	A	A	0	B	A	A	0	A	A	A	0	A	A
	Carbohydrates	A	A	A	A	0	B	A	A	A	A	A	A	0	A	A
	Fatty acids-Soap-Micelles	A	A	A	A	0	A	A	A	A	A	A	A	0	A	A
	Cell membranes	A	A	A	A	0	B	A	A	A	A	A	A	0	A	A
	DNA	A	A	A	A	0	A	A	A	A	A	A	A	0	A	A
	Enzymes	A	A	A	A	B	A	A	A	A	A	A	A	0	A	A
	Proteins	A	A	A	B	0	A	A	A	A	A	A	A	0	A	A
	Polymers	A	A	A	A	0	A	A	B	B	B	A	B	0	A	A
	Drugs-receptors	A	A	A	A	0	A	A	B	B	B	A	A	0	A	A
An. Tech.	Infrared	A	A	A	A	B	0	A	A	A	A	A	A	0	A	A
	NMR	A	A	A	0	0	A	0	A	0	0	A	A	0	A	A
	Paper chromatography	0	A	0	0	0	0	0	B	0	0	0	0	0	0	0
	Chromatography - TLC	0	A	0	0	0	0	0	0	0	0	0	0	0	0	0
	Chromatography - Column	A	A	A	A	B	A	C	A	A	A	0	A	B	B	A
	Electrophoresis	A	A	A	0	0	A	A	0	A	A	0	A	0	A	A
Other	Graphite	B	B	B	B	0	B	A	B	0	0	A	A	0	B	A
Other	Crown ether	A	A	A	A	0	A	A	A	A	0	A	A	0	A	A

Type of Interactions	Types of Coverage^a aNotation: A: Topic is explained, and example(s) are provided; B: Topic is not explained, but provide examples; C: Topic is explained, but examples are not provided; 0: Topic is not covered.
Type of Interactions	%A	%B	%C	%0
Ion-induced dipole	0.0	0.0	0.0	100.0
Hydrogen bonding	86.7	13.3	0.0	0.0
London forces	80.0	0.0	0.0	20.0
Dipole-dipole	73.3	6.7	0.0	20.0
Ion–dipole	40.0	53.3	0.0	6.7
Dipole-induced dipole	6.7	6.7	0.0	86.6

Physical Properties	Types of Coverage^a aNotation: A: Topic is explained, and example(s) are provided; B: Topic is not explained but provides examples; C: Topic is defined, but examples are not provided; 0: Topic is not covered. bForm of the meniscus and the drop.
Physical Properties	%A	%B	%C	%0
Boiling point	80.0	13.3	0.0	6.7
Melting point	80.0	13.3	0.0	6.7
Solubility	73.3	26.7	0.0	0.0
Density	40.0	20.0	0.0	40.0
Vapor pressure	0.0	20.0	0.0	80.0
Surface tension	0.0	13.3	0.0	86.7
Adhesion-cohesion	0.0	0.0	0.0	100.0
Capilarity	0.0	6.7	0.0	99.3
Viscosity	0.0	13.3	0.0	86.7

Biomolecules	Types of Coverage^a aNotation: A: Topic is explained, and example(s) are provided; B: Topic is not explained but provides examples; C: Topic is defined, but examples are not provided; 0: Topic is not covered.
Biomolecules	%A	%B	%C	%0
DNA	86.7	0.0	0.0	13.3
Soap-Micelles	86.7	0.0	0.0	13.3
Proteins/Enzymes	86.7	6.7	0.0	6.6
Carbohydrates	80.0	6.7	0.0	13.3
Cell membranes	80.0	6.7	0.0	13.3
Cellulose and Starch	73.3	6.7	0.0	20.0
Drugs-receptors	66.7	20.0	0.0	13.3

Analytical Techniques	Types of Coverage^a aNotation: A: Topic is explained, and example(s) are provided; B: Topic is not explained but provides examples; C: Topic is explained, but examples are not provided; 0: Topic is not covered.
Analytical Techniques	%A	%B	%C	%0
Infrared	80.0	6.7	0.0	13.3
NMR	60.0	0.0	0.0	40.0
Paper Chromatography	6.7	6.7	0.0	86.6
Chromatography - TLC	6.7	6.7	0.0	86.6
Column Chromatography	66.7	20.0	6.7	6.7
Electrophoresis	66.7	0.0	0.0	33.3

Topics	Types of Coverage^a aNotation: A: Topic is explained, and example(s) are provided; B: Topic is not explained but provides examples; C: Topic is explained, but examples are not provided; 0: Topic is not covered. b Meniscus and drop shapes.
Topics	%A	%B	%C	%0
Dyes and dyeing	13.3	33.3	0.0	53.3
Meniscus and drop^b aNotation: A: Topic is explained, and example(s) are provided; B: Topic is not explained but provides examples; C: Topic is explained, but examples are not provided; 0: Topic is not covered. b Meniscus and drop shapes.	6.7	0.0	0.0	93.3
Salting-out effect	0.0	0.0	0.0	100.0
Polymers	60.0	26.7	0.0	13.3

Category	Topics	Textbooks
Category	Topics	Brown²¹21 Brown, W. H.; Iverson, B. L.; Anslyn, E.; Foote, C. S.; Organic Chemistry, 6th ed.; Cengage Learning: Boston, 2012.	Bruice²²22 Bruice, P. Y.; Organic Chemistry, 7th ed.; Pearson: New York, 2014.	Carey²³23 Carey, F.; Giuliano, R.; Allison, N. T.; Bane, S. L.; Organic Chemistry, 7th ed.; McGraw-Hill: New York, 2008.	Jones Jr.²⁶26 Jones, M.; Fleming, S. A.; Organic Chemistry, 4th ed.; W. W. Norton & Company: New York, 2010.	Klein²⁷27 Klein, D.; Organic Chemistry, 3rd ed.; Wiley: Hoboken, 2016.	Loundon²⁸28 London, M.; Parise, J. Organic Chemistry, 6th ed.; W. H. Freeman and Company: New York, 2016.	McMurry²⁹29 McMurry, J. E.; Organic Chemistry, 8th ed.; Cengage Learning: Boston, 2012.	McMurry³⁰30 McMurry, J. E.; Organic Chemistry Biological Applications, 2nd ed.; Cengage Learning: Boston, 2011.	Smith³¹31 Smith, J. G.; Organic Chemistry, 3rd ed.; McGraw-Hill: New York, 2008.	Solomons³²32 Solomons, T. W. G.; Fryhle, C. B.; Snyder, S. A.; Organic Chemistry, 10th ed.; Wiley: Hoboken, 2011.	Stowell³³33 Fabirkiewicz, A. M.; Stowell, J. C.; Intermediate Organic Chemistry, 3rd ed.; Wiley: Hoboken, 2016.	Vollhard³⁴34 Vollhardt, K. Peter C.; Organic Chemistry: Structure and Function, 6th ed.; W. H. Freeman and Company: New York, 2011.	Wade Jr.³⁵35 Wade, L. G.; Simek, J. W.; Organic Chemistry, 6th ed.; Pearson: New York, 2006.	Total
Type	Identification of interaction	02	01	03	02	01	01			08				02	20
Physical proprieties	Boiling point	15	08	06	01	04	09			25	06	01	03	08	86
	Melting point	03	05	01	01	04	03	01	01	08					27
	Solubility	13	09	02	01	02	19	01	01	20	06	01	03	07	85
	Density	03	01				01								05
	Vapor pressure
	Surface tension
	Adhesion-cohesion
	Capilarity
	Viscosity
	Physical state									01					01
Biomolecules	Cellulose and Starch
	Carbohydrates
	Fatty acids-Soap-Micelles	04								03			01		08
	Lipids	01													01
	Cell membranes	01													01
	DNA	04						01	01						06
	Proteins-Enzymes	03	01												04
	Drugs-receptors
An. Tech.	Infrared
	NMR
	Paper chromatography
	Chromatography - TLC
	Chromatography - Column
	Electrophoresis
Other	Graphite
	Crown ether
	Meniscus and drop format
	Dyes and dyeing
	Salting-out effect
	Polymers
Total of the problems on IMFs		44	21	09	04	11	32	03	03	51	12	01	06	15	212*
% of the problems on IMFs		3.0	1.1	0.6	0.3	0.6	1.7	0.2	0.2	2.4	0.9	0.0	0.4	1.1

Category	Number of Problems
Category	Total^b aOther: Graphite, crown ether, meniscus and drop shape, dyes and dyeing, salting-out effect, and polymers. bThere were problems related to more than one topic.	%
Type	20	8.2
Physical properties	204	83.6
Biomolecules	20	8.2
Anal. Techniques	00	0.0
Other^a aOther: Graphite, crown ether, meniscus and drop shape, dyes and dyeing, salting-out effect, and polymers. bThere were problems related to more than one topic.	00	0.0
Total	244	100.0

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