Innovative ESP Teaching Practices and Materials Development

Abstract

As tertiary-level students progress in their studies, they reach a point where they need to read and write the genres valued in their chosen disciplines. The transition from general academic English to English for specific purposes (ESP) begins at this juncture. ESP instruction facilitates this transition by equipping students with the language and genre-analysis skills needed to access their respective disciplinary genres. In this chapter, we introduce two approaches to ESP instruction that can be sequenced to ease students’ progression toward disciplinary literacy. With the read–and–notice approach, ESP students are guided in noticing, comparing, and contrasting written disciplinary conventions. This pre-production stage serves as preparation for the later read–analyze and write approach. To illustrate what can be accomplished with both approaches, we highlight innovative teaching practices and materials developed specifically for students in an organic chemistry lab and in a subsequent reading-and-writing intensive course for chemistry majors. Particular attention is paid to an online read-and-notice module integrated into an organic chemistry lab. Examples from ten online assignments are provided, and implications for other disciplines are discussed.

Appendix

Example A1: Experimental Section (Capitalization)

Which of the following sentences use capitalization correctly? Use your lab manual and the JOC article as guides.

• High-purity CH₄ was used as the carrier gas. (correct)

• The more polar solvent was ethanol. (correct)

• Thin-layer chromatography (TLC) was used to separate a mixture of ferrocene and acetylferrocene. (correct)

• The eluent was collected in an erlenmeyer flask. (incorrect – Erlenmeyer is capitalized because it is named after a person)

• The gases used were Oxygen, Nitrogen, and Helium. (incorrect, written-out names of elements or compounds are in lowercase)

Example A2: Experimental Section (Abbreviations)

Chemists are expected to use standard abbreviations in their writing. To practice this skill, fill in the following blanks with the correct abbreviation using the attached list of abbreviations from JOC. Be sure to capitalize and punctuate correctly.

• aqueous ________ (aq)

• concentrated ________ (concd)

• compound ________ (compd)

• gas chromatography _________ (GC)

• hour(s) ________ (h)

• literature value ________ (lit.)

• room temperature _____ (rt)

• temperature ________ (temp)

• thin-layer chromatography ________ (TLC)

• volume ________ (vol)

• weight ________ (wt)

Example A3: Experimental Section (Describing Materials)

In this exercise, we compare how materials are described in lab manuals and journal articles.

• (1) Consider the Materials section of the Diels-Alder reaction in your lab manual. Which statements are TRUE about the ways in which materials are described? Select all that are correct. (Correct answers are A, B, C, and F)

  • A. Physical properties of the reagents used, such as MW and mp, are listed in a table.

  • B. The amounts of reagents used are listed in a table.

  • C. Hazards associated with each reagent are listed in a table.

  • D. Physical properties and hazards of potential products are listed in a table.

  • E. The expected amount of each potential product is listed in a table.

  • F. The equipment you will use is reported in a bulleted list, for example:

    • 25 mL roundbottom flask

    • 250 mL beaker

    • Büchner funnel

• (2) Now let’s examine how materials are described in an organic journal article. Browse through the following excerpt from JOC (adapted from Colomer et al. 2016).

Materials and Methods. Reagents and solvents were handled using standard syringe techniques. All reactions were carried out under an argon atmosphere. Diisopropylamine (i-Pr₂NH) was purified by distillation from CaH₂. Aldehydes were purified by distillation and stored over Na₂SO₄. Anhydrous solvents were purified by filtration on a solvent purification system (SPS). Crude products were purified by flash chromatography on 230–400 mesh silica gel with distilled solvents. Analytical TLC was carried out on silica gel plates with detection by UV light or 10% phosphomolybdic acid solution in ethanol. All reagents were commercial products. Through this section, the volume of solvents is reported in mL/mmol of starting material.

Which of the following sentences are TRUE in the JOC excerpt above? Select all that apply. (Correct answers are A, D, F, and G.)

• A. Unlike the lab manual, chemical information about compounds is not listed in Tables.

• B. A list of chemicals is included but in sentence format, for example: The following chemicals were used: (1) anhydrous ethanol, (2) THF, (3) Na₂SO₄, and (4) diisopropylamine (i-Pr₂NH).

• C. Instead of tables, physical properties (e.g., mp, MW) are reported in the text.

• D. Purification procedures are briefly described.

• E. Vendor information is included (e.g., Sigma Aldrich).

• F. The entire section is written in full sentences (no bulleted lists or fragments).

• G. The section is largely written in past tense.

Example A4: Experimental Section (Describing Procedures)

This activity has four questions.

• (1) Refer to the Grignard reaction in your lab manual. Go to Procedure, Preparing the Grignard Reagent. The procedure is described in 15 numbered steps. What verbs are used at the start of the first five steps? (The answers are Pack, Obtain, Assemble, Remove, and Weigh.)

• (2) Journal articles describe procedures quite differently than lab manuals. Here are three key differences:

  • Steps are not numbered or listed. Everything is written in prose (full sentences).

  • Imperatives (verbs such as Weigh, Add, Stir, Combine) are not used.

  • Sentences are written primarily in the past tense.

With that in mind, compare these two sentences:

• Lab manual: 1. Stir the mixture at 0 °C for 20 min.

• Journal article: The mixture was stirred at 0 °C for 20 min.

Using the example above, rewrite the following sentence for a journal article. Type your answer in the box provided. Be sure capitalization, units, punctuation, and spelling are correct. (You can copy and paste as needed.) (Answer: The mixture was refluxed at 140 °C for 10 min.)

• Lab manual: 4. Reflux the mixture at 140 °C for 10 min.

• Journal article: ___________________________________

• (3) Consider the following six-step procedure from a lab manual:

  • 1. Obtain 15 mL of ethanol and place it in a 125 mL Erlenmeyer flask.

  • 2. Obtain 20 mL of 2.5 M sodium hydroxide and add it to the Erlenmeyer flask.

  • 3. Obtain approximately 2.0 mL of benzaldehyde and place it in a small vial or test tube.

  • 4. Obtain approximately 1.0 mL of acetone and add it to the benzaldehyde in a vial or a test tube.

  • 5. Using a Pasteur pipet, add the benzaldehyde/acetone mixture slowly (a drop or two at a time, over a period of 5 min) to the ethanol/sodium hydroxide mixture.

  • 6. Allow the reaction to stir at room temperature for 30 min.

In a journal article, these steps would be condensed to no more than two sentences! We have provided an example below; however, some information is missing. Using the lab manual excerpt, fill in the blanks in the journal article excerpt. Your answer must be an exact match and use capitalization, abbreviations, spelling, and punctuation correctly. Note how the authors use parentheses to achieve conciseness.

Benzaldehyde (____) in ____ (1.0 mL) was added dropwise over 5 min to a mixture of ____ (15 mL) and ___ (20 mL, 2.5 M). The reaction was ____ at room temperature for 30 min.

Answer: Benzaldehyde ( 2.0 mL ) in acetone (1.0 mL) was added dropwise over 5 min to a mixture of ethanol (15 mL) and sodium hydroxide (20 mL, 2.5 M). The reaction was stirred at room temperature for 30 min.

• (4) Your thoughts? What key differences did you notice between how procedures are described in a lab manual versus a journal article? Why do you think these differences exist?

Example A5: Results and Discussion Section (Present and Interpret Data)

In exercise A4, you learned that in the Results section, results are shared, and in the Discussion section, results are interpreted. However, because these two sections are combined, results and interpretative remarks are often intertwined. Nonetheless, it is usually possible to distinguish the two. Here are some guidelines:

In the Results, authors highlight the results presented in tables (without repeating them) by

• Calling out the table in the text (e.g., “As shown in Table 1”)

• Describing the results in the table (without repeating the values)

• Summarizing important findings

In the Discussion section, authors

• Interpret their results (often using phrases such as “The results indicated” or “The results suggested”)

• Compare their findings to others’ works

• Propose mechanisms to explain their results

Below we present excerpts from a JOC Results and Discussion section (adapted from Wang et al. 2016). Determine which excerpt is a Result (R) and which is a Discussion (D).

• 1. As shown in Table 1, the desired product could be obtained in moderate yield (68–78%) with varying levels of enantioselective excesses. (R)

• 2. The results indicate that the rate-determining step of the dinuclear zinc catalytic asymmetric reaction may change when the substrate bears a strong electron-withdrawing group. (D)

• 3. To our surprise, when Trost’s ProPenol dinuclear zinc catalyst 7a was examined under the same condition, the enantiomeric excess of the product was up to 97% (Table 1, entry 2). (R)

• 4. Among the ligands screened for the Friedel-Crafts reaction, L ₁ afforded the best results in terms of yield and enantioselectivity (Table 1, entry 2). (R)

• 5. These results suggest that THF not only serves as the reaction media but also acts as a weak catalytic auxiliary in the reaction. (D)

• 6. In further investigation, we used 7a as the catalyst for the Friedel-Crafts alkylation process and various reaction conditions were examined (Table 2). (R)

• 7. When the temperature was raised to 40 °C, ee dropped to 86% (Table 2, entry 7). (R)

• 8. Therefore, the optimal conditions for the enantioselective Friedel−Crafts reaction were as follows: 10 mol% ligand L ₁, 20 mol% ZnEt₂, 2 equiv. of indole 8a to imine 9 in THF at room temperature for 12 h. (R)

• 9. In accordance with the report by Wang,¹¹ when N-methylindole 8w was examined in the catalytic system, no reaction was observed. (D)

• 10. A plausible mechanism for the Friedel−Crafts alkylation process is proposed on the basis of Ding’s X-ray analysis of the zinc complex and our observed results (Scheme 4).^8,9,11 (D)

Example A6: Introduction (Opening Sentence)

Consider the following three sentences from an Introduction in JOC (adapted from Lakshmi and Ravikanth 2013). Which sentence do you think is the first sentence of the Introduction (the opening sentence of the paper)? Your answer will not be graded, but please let us know what you think! We will ask you this question again at the end of the activity. Note: citation numbers have been replaced with “#” to make this more challenging.

• A. Recently, we reported on 3,5-diformyl BODIPYs and demonstrated their use as a pH sensor,^# cyanide sensor,^# and in other applications.^#

• B. In this paper, we report the synthesis of conjugated BODIPYs by carrying out a reaction between formyl BODIPYs and alkyl or aryl ylides under the Wittig reaction conditions.

• C. Among the numerous classes of highly fluorescent dyes, conjugated BODIPY is known to be a versatile and robust fluorophore due to its novel characteristic features and numerous useful applications. (Correct answer)

Example A7: Introduction (Purposes)

The following excerpts are from a JOC Introduction (adapted from Wang et al. 2016). They are in the correct order (that is, the order in which they appeared in the actual article); however, some sentences have been omitted. Your task is to determine the purpose of each excerpt. The purposes are listed below in scrambled order. Match each excerpt with its correct purpose. Each purpose is used only once.

(Answers: 1 = E, 2 = B, 3 = D, 4 = G, 5 = A, 6 = C, 7 = F)

• 1. _____ Optically active nonproteinogenic amino acids have captivated chemists for their biological activities and chemical transformations.¹ (paragraph 1, sentence 1)

• 2. _____ 3-Indolylglycine derivatives can be used as important synthetic intermediates and building blocks in natural and man-made products.² (paragraph 1, sentence 2)

• 3. _____ Several strategies have been reported for their stereoselective synthesis, including asymmetric catalysis,³ use of chiral auxiliaries,⁴ enzymatic resolution,⁵ and dynamic kinetic resolution.⁶ Among these methods, asymmetric catalysis is the most significant and effective approach to prepare these compounds because only a limited quantity of the chirality controlling element is used. (paragraph 1, sentences 3 and 4)

• 4. _____ Wanner et al. developed chiral phosphoric acids 1 and 2 catalytic process for the synthesis of 2-nitrophenylsulfenyl-protected (S)-indolylglycine and triphenylmethylsulfenyl-protected (R)-indolylglycine (Fig. 1).^3a The enantioselective Friedel−Crafts reaction of indoles with ethyl glyoxylate imines utilizing chiral phosphoric acid 3 was described by Kang and co-workers.^3b (paragraph 1, sentences 5 and 6)

• 5. _____ Dinuclear zinc catalysts have also shown excellent performance on asymmetric Friedel−Crafts alkylation reactions … (For example,) Wang et al. reported the Friedel−Crafts amidoalkylation of indoles with aryl aldimines catalyzed by 7a, affording 3-indolyl methanamine derivatives.¹¹ However, only aryl aldimines were tested in their work. (last paragraph, first sentence)

• 6. _____ Herein, we report the dinuclear zinc catalyst system for asymmetric Friedel−Crafts alkylation reaction between indoles and ethyl glyoxylate imine. (last paragraph, next to last sentence)

• 7. _____ What’s more, the products are 3-indolyl α-amino esters. In the presence of 10 mol% catalyst, a series of 3-indolylglycine derivatives were synthesized in moderate to good yields and excellent ee (up to >99%) under mild conditions. (last paragraph, last sentence)

Purposes (in scrambled order)

• A. Identify a gap (or gaps) (i.e., shortcomings) in previous works, suggesting the need for further research.

• B. Highlight the importance of the research area.

• C. Introduce the current work (i.e., the work presented in the article) as a way to fill gaps left in others’ works.

• D. Provide essential background information (previous accomplishments in this area).

• E. Introduce the general research area.

• F. Preview key findings of the current work.

• G. Highlight and cite previous works in the research area.

Example A8: Introduction (Scrambled Purposes)

Consider the purposes of the Introduction again, this time reduced from seven to four. Based on your answers to the previous question, arrange these purposes in their correct order. (Answer: 3, 1, 4, 2)

• 1. Provide background information and cite others’ works.

• 2. Introduce the current work (that will fill the gap).

• 3. Identify the general research area and its importance.

• 4. Identify a gap in the research area (work that still needs to be done).

Example A9: References

JOC, Org. Lett., and Tetrahedron all recommend similar guidelines. Here are three examples of a reference format used in JOC (from Kumar et al. 2017):

• (1) Koelle, P.; Noeth, H. Chem. Rev. 1985 , 85, 399–418.

• (2) Piers, W. E.; Bourke, S. C.; Conroy, K. D. Angew. Chem., Int. Ed. 2005 , 44, 5016–5036.

• (3) Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996 , 118, 5502–5503.

Examine the three JOC references above, paying careful attention to detail (e.g., spacing and punctuation). Below we have listed eight references (adapted from Georgiou et al. 2017), but only one matches the JOC format above. Which one is it? Note the differences are quite subtle! Assume that all articles are at least three pages in length. (Answer: reference 5)

• (1) Pelly SCA; Govender S; Fernandes MA; Schmalz H-G; de Koning C. J. Org. Chem. 2007, 72, 2857–2861.

• (2) Habib A. M., Masuda S., McCloud T. J. Org. Chem. 1987, 52, 412–415.

• (3) La Forge F. B.; Haller H. L.; Smith L. E. Chem. Rev. 1933, 181.

• (4) Pastine S. J.; Sames D. Concise Synthesis of the Chemopreventitive Agent (±)-Deguelin. Org Lett. 2003, 5, 4053–4055.

• (5) Akselsen O. W.; Skattebol L.; Hansen T. V. Tetrahedron Lett. 2009 , 50, 6339–6342.

• (6) Büchi G.; Crombie L.; Godin P. J.; Kaltenbronn J. S.; Whiting D. A. J. Am. Chem. Soc. 1961, 2843–2848.

• (7) Undeani G. O. et al. Cancer Res. 1997, 57, 3424–3428.

• (8) Alonso, Rafael; Campos, Pedro. J.; Garcia, Barabara; Rodriguez, Miguel A. Org. Lett. 2006, 8, 3521–3526.

Example A10: Citations

Immediately below the following JOC excerpt (adapted from Lakshmi and Ravikanth 2013), we list 10 rules regarding in-text citations. Some are correct and some are incorrect. Using the JOC excerpt for guidance, which rules are correct for JOC? There is more than one correct answer. (Answer: 2, 3, 5, 6, 10)

JOC excerpt (from the Introduction)

Among the numerous classes of highly fluorescent dyes, 4,4-difluoro-4-bora-3a,4a–diaza-s-indacene (BODIPY) is known to be a versatile and robust fluorophore due to its novel characteristic features and numerous useful applications. The novel features of BODIPY include robustness against light and chemicals, relatively high molar absorption coefficients and fluorescence quantum yields, negligible triplet formation, narrow emission bandwidths with high peak intensities, good solubility, resistance toward self-aggregation in solution,¹ excitation/emission wavelengths in the visible spectral region (>500 nm), and fluorescence lifetimes in the nanosecond range.² BODIPY dyes have been shown to be promising for a variety of applications including use as biological labels,^1,3 electroluminescent devices, tunable laser dyes,⁴ potential candidates for solid-state solar concentrators,⁵ fluorescent switches⁶ and fluorophores in sensors, and potential photosensitizers in photodynamic therapy of cancer.^1,7 Moreover, the spectroscopic and photophysical properties of BODIPYs can be fine-tuned by attachment of ancillary residues at the appropriate positions of the BODIPY core⁸ by carrying out various synthetic reactions on BODIPYs. The various synthetic strategies available for the modification of the BODIPY core are electrophilic substitution,⁹ condensation reactions,¹⁰ substitution of the fluorine atoms,¹¹ direct substitution of the hydrogen atoms,¹² and transition-metal catalyzed reactions through the use of halogenated systems.^13–17

Which of the following rules are correct? There is more than one correct answer.

• ____1. Citations are placed only at the end of a sentence.

• ____2. Citations can be placed in a sentence.

• ____3. Citations are placed after commas, not before.

• ____4. At the end of the sentence, citations are placed before the period.

• ____5. A work should be cited each time it is referenced, not just the first time.

• ____6. Two citations that are not sequential are separated by a comma.

• ____7. The authors’ names must be included in the sentence that cites their work.

• ____8. Only one work should be cited in a sentence.

• ____9. Direct quotes (where an author is cited word-for-word rather than paraphrased) are common in chemistry writing.

• ____10. Citations are numbered in numerical order (1, 2, 3, …).

Example A11: Use of et al.

Although most citations omit the names of the authors (for conciseness), authors’ names are occasionally included. In such instances, et al. (meaning “and others”) is used if the cited work has at least three authors. For one or two authors, the last names of the authors are written out. Consider the following examples (adapted from Wong and Wong 2007):

Inoue et al.³ achieved anti- and syn-aldol products of carboxylic esters using combinations of a boron triflate and an amine.

Ohkouchi et al.¹⁷ have shown that the silver(I) carboxylate-BINAP catalyst coordinated to the nucleophile in Mukaiyama aldol reactions; the activated complex then attacked the aldehyde to afford the aldol adduct.

Solid-state characterization of a trichlorotitanium aldolate has been reported by Cozzi and Floriani.¹³

Using the sentences above for guidance, correct the following citations if necessary. Copy and paste the underlined passage into the box (correct or incorrect), then edit the citation if necessary. (Correct answers are shown in italics.)

• (1) Rurack, Kollmannsberger, and Daub ²⁰ extended pyrroles from 2-formyl pyrroles using Wittig conditions.

Rurack et al. ²⁰ synthesized

• (2) Wong and Thurman ⁴ ab initio calculations to investigate the mechanism of the metal chloride-promoted Mukaiyama aldol reaction between trihydrosilyl enol ether and formaldehyde.

Wong and Thurman ⁴ employed (correct as is)

• (3) When Yanai, Yoshino, Takahashi et al. ¹⁵ used Tf₂CHCH₂CHTf₂, the Mukaiyama aldol reaction of R-substituted cyclohexanones with 2-silyloxyfurans gave the aldol products in excellent yield without loss of diastereoselectivity.

When Yanai et al. ¹⁵ used

• (4) In particular, Mühlthau et al. ¹¹ have reported a highly diastereoselective Friedel−Crafts alkylation of 1-arylalkanoles via the formation of chiral benzylic carbocations.

Mühlthau et al. ¹¹ have reported