Teaching and the Internet: The Application of Web Apps, Networking

This chapter discusses the efficient use of iOS- and. Android-based tablet/mobile device applications to enhance student learning in and out of the ch...
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Ganesh H. Naik* Chemistry Department, College of Saint Mary, 7000 Mercy Road, Omaha, Nebraska 68106, United States *E-mail: [email protected]

Mobile devices such as smartphones and tablets are becoming increasingly common in the lives of students in the 21st century. If web-based technology is astutely integrated into the students’ course curriculum, it will help both students and educators meet course objectives and course learning outcomes more effectively. This chapter discusses the efficient use of iOS- and Android-based tablet/mobile device applications to enhance student learning in and out of the chemistry classroom. Subject areas covered include general and organic chemistry.

Introduction Chemistry education teaches us an understanding of the fundamental building blocks of the universe and everything in it. In my personal experience as an educator, I have observed that many students find it difficult to understand chemistry, as it has a vocabulary quite different from their everyday communication. To understand and apply the fundamental concepts of chemistry, it requires a greater amount of effort from students, both in and out of the classroom. There are 118 elements on the periodic table to study and understand. Chemical bonding is a theoretical concept and very abstract. Furthermore, students find it difficult to visualize the physiochemical properties of the molecules and the dynamics of chemical bonding and intermolecular forces. This requires not only scientific literacy, but also an imagination.

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As chemistry educators, it is important to recognize these difficulties and to utilize different teaching strategies to enhance the students’ learning experience in the classroom, as well as provide viable and relevant resources for self-study. One such strategy includes integrating mobile apps into the course curriculum and classroom instruction (1, 2). With the advent of the internet and the evolution of smartphones and tablets, students have instant access to a wealth of information (1). Of course, adopting and integrating technology-based instructional strategies has had a long history of challenges. Hew and Brush identified the general barriers typically faced when integrating technology into the curriculum for instructional purposes (3). A lack of resources and the knowledge and skills of how to best utilize these technologies are some of the primary barriers discussed. However, educators such as Pacansky-Brock have developed a great understanding of how to achieve success with these emerging technologies (2). Mobile devices such as iPads and iOS/Android-based smartphones are now an integral part of students’ lives. They are very portable and offer instant access to a library of information via the internet, the world’s greatest database (2, 4). This chapter discusses the strategies for adopting mobile app technology in Fundamentals, General and Organic chemistry course curricula, and the educational benefits of using iOS- and Android-based tablet/mobile device applications. Additionally, the term “apps” will encompass the statement “iOSand Android-based tablet/mobile device applications”. In the following chapter, if the operating system is specified in parenthesis after the mobile app name, this means the app is available only on that platform. For example, ESmol & NDKmol app (Android) means these apps are only available for Android users. If the operating system is not specified, it means the app is available for both iOS and Android device users. The mobile app pricing is not mentioned in the chapter, as it varies based on the promotional offers.

Mobile Apps in Classroom Instruction Historically, traditional classroom lecture presentations were typically done using ‘chalk talk’ or using projector slides. In the first decade of the 21st century, Microsoft Office became a ubiquitous technology, and most educators switched from projector slides to Microsoft PowerPoint. However, these methods of instruction continue to have limited interaction with the students, especially with large class sizes. There are many research studies, from many disciplines, that suggest that oral presentations to large groups of passive students contribute very little to real understanding; and student grades, by and large, do not correlate with the lecturing skills and/or experience of the instructor (5, 6). Despite the limitations of traditional lectures, many institutions are obliged to offer high-enrollment General Chemistry and Organic Chemistry courses. Many professors who teach these courses find lecturing to be the most viable option for covering all of the necessary subjects presented in the syllabus (7). However, traditional lecturing often increases boredom among students, causing a deficit to learning. A research study by Mann and Robinson found a positive relationship 20 Christiansen and Weber; Teaching and the Internet: The Application of Web Apps, Networking, and Online Tech for ... ACS Symposium Series; American Chemical Society: Washington, DC, 2017.

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between boredom and attentional problems, while a negative relationship existed between boredom and academic performance studies (8). There are several ways to help students make the transition from passive listeners to active participants in their own learning. One such strategy includes integrating mobile apps into the course curriculum and classroom instruction (9, 10). In a study by Rogers and Mize on first-year college students’ perceptions of integrating technology into the curriculum, student feedback confirmed the usefulness of technology in course design and how it contributes to student success (11). Given modern students’ familiarity and comfort with them, apps have become easy-to-use educational tools. Instructors can make lectures more interactive by projecting apps from their smartphone or tablet onto a projector screen, provided the classroom is equipped with it. The instructor may need a HDMI/VGA adapter and extension cable to connect to the projector, as shown in Figure 1.

Figure 1. HDMI adapters and cables to display the mobile apps on the classroom projector screen.

Mobile app technology is an alternative method of course instruction that can be used in conjunction with traditional classroom PowerPoint and whiteboard presentations. By using apps, the instructor can demonstrate how to build an atom, display interactive periodic tables of elements, molecular bonding and 3-D images, and much more. Apps provide an inexpensive and mobile alternative to traditionally high-priced chemistry software that is restricted to the classroom (9, 10, 12, 13). Another benefit of apps is using polls in the classroom to engage all students concurrently. For example, an instructor may use a polling app after a new subject is covered to determine how many students are understanding the concept. This allows students to respond without the fear of being singled out or feeling embarrassed/uncomfortable raising their hands.

Mobile Apps for Learning General Chemistry Concepts Technology such as iOS and Android based mobile apps can be used as an interactive educational tool, which allows for a dynamic learning experience that directly benefits students (10, 12, 13). Figure 2 shows some of the mobile apps that can be used in a General Chemistry course to teach the subjects of atoms, elements, and the periodic table. Because these apps are interactive, they enhance student engagement and spark interest in learning these fundamental concepts. 21 Christiansen and Weber; Teaching and the Internet: The Application of Web Apps, Networking, and Online Tech for ... ACS Symposium Series; American Chemical Society: Washington, DC, 2017.

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Figure 2. Mobile apps for Atoms, Elements, and Periodic table.

iOS and Android apps offer educators an interactive teaching platform to engage students both inside and outside the classroom. For example, Figure 3 represents the periodic table, expressed through a mobile app developed by Theodore Gray, which goes far beyond what is possible on paper or in a simple digital image. Students can click on and experience beautiful images of each element (often in a variety of forms or states), as well as read engaging stories about the elements and detailed lists of their properties. Every image is a freely rotatable, live object that students can examine from all angles. In my personal experience as an educator, I have found that students often have difficulty making the transition between 2D molecular drawings and visualizing 3D molecular structures. This mobile app also allows for students to recognize these elements as real and individual objects, as opposed to just chemical symbols. Moreover, having all of this information on a single platform enables students to see relationships between properties (such as commonalities between freezing/boiling points of certain elemental groups) and thereby gain a deeper understanding of the elements and chemistry as a whole. In addition, Theodore Gray also developed the Elements in Actions app, which is a collection of 77 video demonstrations of wonderful chemical reactions of the elements. He also developed the Molecules app, with brilliant visuals, and The Elements Flash card app, which helps in learning element names, symbols, and atomic numbers quickly. Figure 4 lists the four mobile apps developed by Theodore Gray.

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Figure 3. Screenshot of Theodore Gray’s Periodic Table Application. Image courtesy of Theodore Gray/Touch Press.

Figure 4. Mobile apps suite developed by Theodore Gray. Icon images courtesy of Theodore Gray/Touch Press.

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There are many mobile apps available for studying the periodic table concept. However, the Quick Response-coded Audio Periodic Table of the Elements (QRAPTE) is a unique web-based tool. QR-APTE is particularly useful for blind and visually impaired students, as well as seeing students (14). It uses the QR code technology (a two-dimensional barcode that was originally developed in 1994 by Denso Wave, a Japanese automatic data-capture equipment company) to present the information about the elements in the periodic table. The QR-APTE poster was built up using the audio PTE “Chemistry in its Element” from the Royal Chemistry Society (RSC) website. The URLs of the RSC podcast audio files contain general information (history and applications) about the chemical elements. The poster of QR-APTE material is available online (15). After introducing the atoms, elements, molecules and periodic table apps, students can learn basic electronic configuration, shapes of atomic orbitals and coulumbic interactions between ions using the apps shown in Figure 5.

Figure 5. Mobile apps for electronic configuration and chemical bonding. In an introductory chemistry class, many students find learning about chemical bonding to be challenging, as the level of abstraction is high. Furthermore, students need to understand the different chemical bonding theories (Lewis dot structures, VSEPR, Hybridization, molecular orbital theories.) Each theory uses different postulates to explain the bonding in molecules. Mobile apps aid the learning process by making it more interactive and fun. Figure 6 represents the different apps that can be used for learning chemical bonding in molecules. The Chem101 app (by 101 Edu Inc) features a custom-built tool that allows users to draw and understand Lewis structures. Additionally, it has over 200 questions related to Lewis structures, resonance, molecular geometries, VSEPR, hybridization, sigma and pi bonding, and molecular polarity. The ChemEd: Bonding & Structures app (Android, by Advanced Mobile Apps for Science & Education) allows users to visualize bonding in a molecule using Molecular Orbital theory. The students can also explore concepts such as electrostatic potential surface and polarity, orbital hybridization, etc. The 3D Molecules Edit 24 Christiansen and Weber; Teaching and the Internet: The Application of Web Apps, Networking, and Online Tech for ... ACS Symposium Series; American Chemical Society: Washington, DC, 2017.

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& Test app (iOS, by Virtual Space OOO) has a tool to build molecules with single, double and triple bonds, as well as cyclic compounds. The molecules can be visualized in 3-D using a stick, ball and stick, and space-filling (CPK) models.

Figure 6. Mobile apps for chemical bonding theories.

In addition to bonding in molecules, the molecular viewing apps shown in Figure 7 and 8 such as Atomdroid (Android, by CCB Goettingen), Molecules (iOS, by Sunset Lake Software), ESmol & NDKmol (Android, both by Biochem_fan), Molecules (Android, by ZKM Karlsruhe), Mo-cubed (Android, by Advanced Mobile Apps for Science & Education), iSpartan (by Wave function) and Quiztallography (Android, by Lluís Casas Educational), allow students to create and interact with 3-D molecular structures (4, 10, 16, 17). For simple molecules, students can create the 3-D structure on their devices using the available tools in the program and compare their virtual images with molecular model sets available in the classroom. For complex biomolecules, ESmol & NDKmol apps offer a greater advantage, as these apps are compatible with the downloadable protein files from the Protein Data Bank (18). The information from the downloaded files can be used to display the three-dimensional structures of proteins. In addition, it offers several interactive tools which can be used to change the representation of protein or ligand (nonprotein) molecules. The ESmol app is more compatible with older devices, but NDKmol, the newer version of the app, offers more features. Mo-cubed is an advanced molecular modeling app. In addition to the 3D viewing of molecules, it can search for chemical and spectral information (IR, proton and carbon-13 NMR, mass spectrum) available on public databases. Mo-cubed uses a semi-empirical molecular orbital method from the MOPAC2012 program to enable users to both assess chemical information in 3-D and perform quantum chemistry calculations. MOPAC (Molecular Orbital PACkage) is a semi-empirical quantum chemistry program based on Dewar and Thiel’s NDDO approximation. 25 Christiansen and Weber; Teaching and the Internet: The Application of Web Apps, Networking, and Online Tech for ... ACS Symposium Series; American Chemical Society: Washington, DC, 2017.

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Figure 7. Molecular viewing mobile apps.

Figure 8. Advanced molecular viewing apps.

The iSpartan app is also an advanced molecular modeling app, which has a database of over 5000 molecules. It allows 3-D visualization of molecules, IR, proton, and carbon-13 NMR spectral information, molecular orbitals, electrostatic potential maps, and molecular properties. In the IR spectrum of a given molecule, if a student selects a particular peak, the appropriate bonds in the displayed three-dimensional model vibrate to show the stretching or bending vibration responsible for the chosen peak. This interactive experience gives students a better understanding of bond vibration and the IR spectrum. Wavefunction, Inc. has developed several iOS-based apps for the 3-D visualization of molecules and ionic solids as a part of the ODYSSEY suite. Quiztallography, a quiz game app, contains over 1000 questions on crystallography and symmetry concepts. Using this app, students can improve their skills on different symmetry operations in a molecule (17). 26 Christiansen and Weber; Teaching and the Internet: The Application of Web Apps, Networking, and Online Tech for ... ACS Symposium Series; American Chemical Society: Washington, DC, 2017.

Mobile Apps for Learning Organic Chemistry Concepts

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Students in sophomore organic chemistry classes use flashcards to memorize the functional groups and chemical reactions. The apps shown in Figure 9 can essentially replace the traditional flashcards and make the learning process more interesting and interactive (4, 19, 20). These include Chemistry By Design (by The University of Arizona), Awesome Organic Chemistry Flashcards (iOS, by Jacob Kearns), Organic Reactions (by Turvy education), Reagents (iOS, by Metamolecular), Organic Chemistry Practice (not pictured, by Varsity Tutors) and ReactionFlash (by RELX Intellectual Properties SA).

Figure 9. Mobile apps for learning organic chemistry reactions.

Chemistry by Design is an app that summarizes the total synthesis routes of 337 compounds and enables students to test their skills using known synthetic sequences. The quiz tool assesses the students’ knowledge of reactants, reagents, or products in each step of the synthesis reaction involving natural products or pharmaceutical drugs. The synthetic routes are also categorized by name, author, year, and drugs, which can be searched within the app. The Awesome Organic Chemistry Flashcards app presents a quiz interface to review introductory organic chemistry concepts. Topics covered include organic chemistry nomenclature, functional groups, and addition/substitution/elimination/ coupling reactions. Organic Reactions is an app that provides information on different functional group reactions and their mechanisms. It is organized to provide information on synthesis and protection reactions of each functional group. The Reagents app covers the structures and functions of over 90 reagents encountered in a typical introductory organic chemistry course. Reactions can be explored from three perspectives: reagents, reactants, and products. It also helps build an understanding of how different reactions can be carried out by the same reagent and highlights the influence of reagents on the products’ stereochemistry. 27 Christiansen and Weber; Teaching and the Internet: The Application of Web Apps, Networking, and Online Tech for ... ACS Symposium Series; American Chemical Society: Washington, DC, 2017.

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The Organic Chemistry Practice app covers many topics in organic chemistry. It has diagnostics tests, practice tests, and interactive flashcards. Students taking a diagnostic test receive a detailed report of their score, broken down by concept area. It also features a question of the day that students can subscribe to and receive a daily practice question in organic chemistry. The ReactionFlash app covers over 600 named chemistry reactions. The app can be used as flash cards, as each ‘card’ shows the reaction, its mechanism, and relevant references. It also has a quiz mode that students could use to practice the reaction. Aaron M. Hartel has developed many apps for the iOS platform, as shown in Figure 10. These apps allow students to practice organic chemistry nomenclature and reactions.

Figure 10. Organic Chemistry apps by Aaron M. Hartel. The Nomenclature apps cover step-by-step approaches to naming organic compounds, identifying the parent chain, substituents, and functional group priorities. They also include quizzes for each lesson with a fill-in-the-blank answer style. The Reaction Cards apps cover most of the functional groups and over 170 reactions encountered in a sophomore year, two-semester organic chemistry course. The format is similar to index cards. The home screen shows a menu of four options to be tested: named reactions, reactants, missing reagents, and missing products. Students can set up a virtual deck of flash cards to study for each of the above options. The app also provides information on stereoselectivity, regioselectivity and the limitations of the reactions.

Mobile Apps for Chemistry Labs iOS and Android based apps also extend the benefits of mobile devices to chemistry laboratory learning (21–23). Figure 11 shows some of the apps that can 28 Christiansen and Weber; Teaching and the Internet: The Application of Web Apps, Networking, and Online Tech for ... ACS Symposium Series; American Chemical Society: Washington, DC, 2017.

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be used in chemistry lab experiments. The following section discusses the many uses of these apps for enhancing laboratory learning.

Figure 11. Mobile apps for chemistry lab experiments.

Titration ColorCam (TCC) is an Android-based application which is used in volumetric titration to determine the end point of the titration. This app is very useful for color blind and visually impaired students (22). The app uses the camera function of a smartphone to capture and quantify the information involved in a color change during a titration experiment. The quantified data is converted into both audio (beep sounds) and tactile (device vibration) feedback for the determination of the end point. The TLC timer app (Android, by Chemovix) and TLC Chemistry tools app (iOS, by PoChu Hsu) are useful in Organic Chemistry Lab to run Thin-Layer Chromatography (TLC) experiments. They can be used for calculating the retention time in TLC as students can take a picture of the TLC plate using the apps. The programs in apps help to map the spots made by the analytes and calculate their Rf values. After the experiment, digital images can be copied, printed or stored for future reference. Agilent Technologies, Inc. developed several apps such as LC Calc., GC Calc., XF Dilution Calculator and ICP-MS Mobile for iOS devices (10). The LC and GC Calculator apps quickly calculate flowrate and back pressure under a variety of conditions and column dimensions, which allows students to explore “what if” scenarios during the experiment. These apps are a beneficial tool for students as they are learning chromatographic separation techniques in any upperlevel chemistry courses. Shimadzu UV is a UV spectrophotometry app that provides basic information on solvent characteristics, which include the lower limit of usable wavelength, melting and boiling point values, etc. for each solvent. It also has a unit conversion tool (ex. wavelength to wavenumber). 29 Christiansen and Weber; Teaching and the Internet: The Application of Web Apps, Networking, and Online Tech for ... ACS Symposium Series; American Chemical Society: Washington, DC, 2017.

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The Insensitive app (iOS, by Klaus Boldt) simulates the quantum mechanical models that are used to describe nuclear magnetic resonance (NMR) experiments. The app provides information on the vector model, density matrix and product operator concepts used in NMR. ChemCrafter (iOS, by Chemical Heritage Foundation) allows students to experiment with water, acids, and salts in a virtual lab environment. The app is designed for younger kids; however, students in an introductory chemistry class may find the app useful. For example, students can learn about the reactions of alkali and alkaline earth metals with water, and the exothermic and endothermic nature of reactions. This app uses a gamified approach to working through experiments. Students must complete each experiment successfully before moving on to the next one. This ensures proper sequencing to build on students’ understanding of the topics. ChemCrafter then provides a brief explanation of the reactions in each completed experiment.

Chemistry Dictionary and Reference Mobile Apps Traditionally used reference dictionaries, such as CRC handbooks or the Merck Index, are bulky and students find it impractical to carry these dictionaries everywhere. The use of mobile apps, shown in Figure 12, has made some of the information found in these reference sources accessible from anywhere. Although they are not comprehensive, they do provide enough information for students in undergraduate chemistry courses. In addition to web-based search engines, students can utilize the following apps to search for chemical information. Most of these apps provide tools to search for chemical information using IUPAC names, common names or chemical structures. W Chemistry Handbook (Android, by Dilithiumlabs) is a comprehensive reference app for the reviewing of basic concepts and techniques. The app organizes the information into six major categories with many subcategories. There are subsections for organic compounds, salts, inorganic acids, gases, and biomolecules. Chemical, physical, and other properties are also listed, as well as a solution calculator tool to practice quantitative skills. It also provides a handy reference for the commonly used constants in general and physical chemistry courses. ChemSpider (by Molecular Materials Informatics) is an app that allows students to search the ChemSpider chemical database provided by the Royal Society of Chemistry. Compounds can be searched by structure or by name. It also has Mobile Molecular Data Sheet information and tools to draw molecular structures. The CRC Physical Constants of Organic Compounds (iOS by Taylor & Francis Group) is an app that allows students to search the physical constants of organic compounds by compound name, CAS number, molecular weight or molecular formula.

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Figure 12. Comprehensive chemistry reference apps.

Chemistry Toolbox (Android by Turvy education) is a good app for quick access to the periodic table, tools for solution preparation (dilution, molar mass, molar concentration and density), organic functional groups, pKa values for organic compounds, information about common organic solvents, buffers, standard reduction potentials and NMR data. The CAMEO Chemicals app (by NOAA ORR Tools) was developed by the National Oceanic and Atmospheric Administration (NOAA) Office of Response and Restoration in partnership with the Environmental Protection Agency (EPA) Office of Emergency Management. It provides hazardous chemical data sheets. Students can search the chemicals by name, CAS number, or UN/NA number to find information from a database of thousands of hazardous substances. The data sheets have information on health hazards, air and water hazards, recommendations for firefighting, first aid, and spill response, and regulatory information. This app could be usefully implemented into the chemistry lab course as a pre-lab assignment. Students must read and document the chemical safety data sheet information corresponding to the chemicals that will be used in the lab.

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A few recently developed apps provide reference information with expanded capabilities. They include IR and NMR tables for organic functional groups, calculation and conversion tools for analytical and physical chemistry, solubility rules and reduction potentials for inorganic compounds. Some include periodic table and information about elements and their properties. Examples of these apps include ChemMobile (Android, by Qan) and Chemistry Helper (Android, by Adam Hogan). Students with an American Chemical Society (ACS) membership can use some of the apps developed by the ACS. The C&EN app provides information on recent advancement in chemistry, the latest chemistry job postings, and other professional development information. The InChemistry app covers special topics of concern to undergraduate students in the chemical sciences, including graduate school, careers, professional development, ACS student chapter activities, and ACS resources for undergraduates.

Assessing Student Learning Using Mobile Apps The intended outcome of integrating mobile apps into teaching and learning is to reinforce the discussion of difficult course concepts and to improve the students’ performance in course examinations. Developing an assessment plan of student learning using mobile app technology is very important, as it helps to determine if the learning goals of the course are being met. Assessment and feedback are crucial for advancing instructional strategies. Apps such as GoSoapBox, Poll Everywhere, and Socrative can be used in the classroom during lecturing for assessment as they allow both polling and open-ended question options. In addition, instructors can develop multiple-choice survey quizzes on a given topic and assess student learning outcomes in real time using these programs. Course management systems, such as Canvas or Blackboard, can also be used to assess student learning outcomes. During the semester, pre- and post-activity surveys and online quizzes can be posted in the course management systems. At the end of the semester, assessment data can be collected in the form of student reflections, course evaluations, and grades. The data collected and collated over the period of a few semesters can be analyzed to assess if student confidence regarding the chemistry concepts has increased significantly. For example, the data collected in my first- and second-year chemistry classes reflected a significant improvement in student performance and attitude towards learning chemistry (24). Figures 13-14 are excerpted from “Integrating Audio-Visual Materials and Mobile App Technologies into Chemistry Course Curriculum”, which demonstrates improvement in student performance following the curriculum update and integration of audio-visual and mobile app technology in the Fundamentals of Chemistry course (24). 32 Christiansen and Weber; Teaching and the Internet: The Application of Web Apps, Networking, and Online Tech for ... ACS Symposium Series; American Chemical Society: Washington, DC, 2017.

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Figure 13. Average student success rate before curriculum update (Letter Grade, %) in a Fundamentals of Chemistry class (n= 30) (24).

Figure 14. Average student success rate after curriculum update (Letter Grade, %) in a Fundamentals of Chemistry class (n=30) (24).

Conclusion iOS and Android based mobile apps are wonderful instructional tools for enhancing student engagement in chemistry courses. In the coming years, the increasing number of high-quality chemistry-related apps will continue to aid in the instruction process and transform the landscape of chemistry teaching and learning. The learning modules based on mobile apps help create opportunities for collaborative activities among students, leading to the development of teamwork and social skills. Another important benefit of mobile apps is that they require minimal expertise and technological proficiency. These tools can be gradually integrated into the coursework, beginning with a few apps in conjunction with the traditional lecturing method. These strategies will help educators develop a better understanding of how to achieve success with mobile app technologies to enhance their instructional methods. Changing existing instructional approaches is a decision that should be considered with deliberate thought, particularly when technology is involved. However, it is important to recognize these challenges 33 Christiansen and Weber; Teaching and the Internet: The Application of Web Apps, Networking, and Online Tech for ... ACS Symposium Series; American Chemical Society: Washington, DC, 2017.

and develop appropriate strategies for continuously reaching and engaging our students.

Acknowledgments The author would like to thank Mary Ramirez, Ashley Reinert and Santosh Shetty for their invaluable assistance in writing this chapter.

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Christiansen and Weber; Teaching and the Internet: The Application of Web Apps, Networking, and Online Tech for ... ACS Symposium Series; American Chemical Society: Washington, DC, 2017.

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35 Christiansen and Weber; Teaching and the Internet: The Application of Web Apps, Networking, and Online Tech for ... ACS Symposium Series; American Chemical Society: Washington, DC, 2017.