Some people and personalities of organic chemistry: a teaching hook for mid-level university students

The teaching hook

Hooks are a pedagogical approach used as an enticement for learning through the development of interest or engagement. A so-called ‘disruptive pedagogy’, hooks employ emotional triggers, critical questions and connections to everyday life to draw students into learning (McCauley et al., 2015). Given the role of hooks within instructional models from the mid-20th century (Atkin & Karplus, 1962; Heiss et al., 1950), they are colloquially a part of every educator’s toolkit. Today, they can be readily observed in the assigned 5E and 6E teaching models with the first E standing for Engagement (Broggy et al., 2015). However, a singular focus on the hook only came about when Schuck (1969, 1970, 1981) first described ‘set induction’. ‘Sets’ (Perrot, 1982) utilize relevant analogies to catch student attention through real-world application. Hunter (2004) expanded on the original concept with ‘anticipatory sets’, defined as any short activity used at the beginning of a lesson to orientate student attention toward learning goals. The term hook was first set in stone, quite recently, by McCrory (2011) although the term was popularized by the idea of hooking an audience (Riendeau, 2013). Throughout the decade, authors have described the use of superheroes (Zehr, 2011), virtual reality (Zavalani & Spahiu, 2012), mysteries (Jewett, 2013; McHugh & McCauley, 2016) and video (McHugh & McCauley, 2015) as methods to hook student interest.

More formal research into hooks started in 2015 with articles exploring the design of hooks in science classrooms, throughout Ireland for example (McHugh & McCauley, 2020), and their associated impact on student participants linked to teachers’ instructional approach and philosophy (McCauley & McHugh, 2021). The authors describe the impact of hooks with an initial triggered reaction from students with observable increases in attention, situational interest and emotional engagement. This was followed by a maintained student reaction, encapsulating continued attention, interest, student persistence and cognitive engagement. Regarding the timing of a hook, the general consensus is that it resides at the start of a lesson. The former paper originated the term ‘para-hook’ as a hook used at time intervals other than at the start of instruction. Another variant is that is Jewett (2013) who proposes using the first lesson/lecture in a series as a hook for an entire semester. The author demarcates students entering classes with a negative perception of ‘fear’ of science. The aim of the first lesson is to hook students on a new topic and using this to drive interest for the rest of the term. Jewett advocates for the use of relevance-based hooks by linking scientific concepts to pervasive topics such as climate change. Indeed, McHugh and McCauley (2020) note relevance as a fundamental hooking method specifically effective at fashioning affective responses from students (Bennett et al., 2007). Relevance in this instance refers to contextual interest through real world applications, past experiences and prior knowledge. The benefits of employing relevance-based pedagogies have been demonstrated to augment to student motivation (Pikaar, 2013), cognitive engagement (Chamany et al., 2008), attitudes toward science (Wellcome Trust, 2011) and interest (Mitsoni, 2006). Relevance can be built into a hook through the use of pop culture (Zehr, 2011), relevant materials (McHugh & McCauley, 2020; Nuora & Välisaari, 2020) or storytelling (Clandos, 2008).

In light of this, a story-based hook grounded in relevancy could provide fruitful avenues for creating student interest and engagement. By chronologically working though examples of prominent organic chemists, the learner can explore the people behind the evolution of science. Often referenced as the ‘historical approach’, this type of storytelling, with a people first approach, has previously been employed as a way to engage students with the Nature of Science (NOS) (Kortam et al., 2021), but to the best of our knowledge, it has never repurposed formally as a hook. The context provides a gap in current knowledge that has potential in the teaching of organic chemistry and in other subject areas.

At university level, complex organic chemistry synthesis, so-called ‘total synthesis’ and ‘retrosynthesis’ (the theoretical, reverse process) are normally dealt with at mid-to late-degree level. At UCC, in the main, retrosynthesis and total synthesis are topics dealt with in Year 3 and 4 (of a 4 year degree course). For many years, students found the topic of synthesis difficult to grasp. Total synthesis is essentially the complete synthesis of a complex molecule, often a natural product, from simple, commercially available precursors. It is often considered one of the most challenging and exciting areas of chemical research (Nicolaou et al., 1998; Nicolaou, 2014). A complex synthesis in usually meticulously planned out on paper before attempting any processes in the laboratory. The synthetic plan involves bringing together numerous differing methodologies and applying these in careful sequence. It is the breadth of knowledge and application that mostly contributes to the difficulty of the topic (Salame et al., 2020).

For the past 10 years, our efforts have focussed on the introductory or ‘hook’ lecture as a way of outlining the history of organic synthesis and total synthesis, through the people (or more specifically the personalities) involved. The lecture narrative chronologically works through the seminal breakthroughs of the 1950 s through the glory days of the 1970 s and 80 s and up to the current leaders of today. The focus is on the people, the circumstances and stories surrounding them. The goal is to inform students of the potential in organic chemistry, through some of the seminal leaders, and thus inspire interest and engagement. The hook methodology will be fully explored in the following section.

The birth of the subject: who started it?

Here we attribute the birth of organic synthesis to Friedrich Wöhler, who in 1828 synthesised urea from potassium cyanate and ammonium sulfate (For a perspective see: Nicolaou et al., 1998; Nicolaou, 2014). Wöhler’s synthesis of urea was followed by other milestones in organic synthesis right up to the Second World War. The interesting, and at the time controversial, aspect of the synthesis of urea, was that a ‘biological’ compound was formed from ‘dead’ or rock-based starting materials. Students recognise that this had all sorts of theological and philosophical consequences.

The early pioneers

Organic synthesis experienced a significant period of growth after the Second World War and this enable the laboratory preparation of nature’s most challenging and beautiful structures. The implemented teaching hook focused on a number of key figures during this time period. An inspirational figure in the field of total synthesis at this time was Robert Woodward (Figure 1). He is considered by many to be the most preeminent synthetic organic chemist of the 20th century, accomplishing the synthesis of many complex natural products during his lifetime.

Figure 1:

Robert Burns Woodward (adapted with permission from Harvard University Archives, HUGFP 68.38.1, olvwork294150).

Considered to be the finest and most inspirational achievements in organic synthesis was Woodward’s chemical synthesis of Vitamin B12. This was the culmination of a 12 year US-Europe collaboration between Woodward and his group at Harvard, and Albert Eschenmoser, a Swiss chemist, and his group at ETH Zurich (Eschenmoser & Winter, 1977; Woodward, 1968). From this, students are able to recognise that the synthesis of such a complex molecule requires a collaborative effort between Woodward’s and Eschenmoser’s extensive research groups. It was important to highlight to the students that achieving work such as this required teamwork both within the groups and across academic institutions. The synthesis of Vitamin B12 involved almost a hundred steps and was underpinned by rigorous planning and meticulous analyses, which characterised all of Woodward’s work (Todd & Cornforth, 1981). At this point, students at UCC are shown a picture of Woodward– quite a stereotypical looking figure at that time, and the stunning structure of Vitamin B12. Students are surprised by the complexity of the structure and the associated synthesis. Given the lack of modern analytical equipment, the assignment of the structures along the way was an equally remarkable achievement. This has important implications in driving student engagement and connection to the topic of total synthesis. If this could be done then, then what can be done now? Woodward received many awards during his illustrious career, culminating with the Nobel Prize in Chemistry in recognition of his outstanding ‘achievements in the art of organic synthesis’ (Woodward, 1965). An inspiration for many organic chemists, Woodward was an exceptionally talented and intelligent individual, whilst also possessing some unusual idiosyncrasies such as giving lectures for an inordinate length of time and having a fixation with the colour blue. He detested exercise, was a heavy smoker, and enjoyed scotch whiskey and martinis (Todd & Cornforth, 1981) (Halford, 2017). These factoids can be humorous, but also humanise complex discoveries and the people behind them.

Leaders in the glory days of the 1980s and 1990s and the Taxol story

Another outstanding leader in total synthesis presented to students is K. C. Nicolaou. Born in Karavas, Cyprus, K. C Nicolaou has distinguished himself as a world leader in the total synthesis of complex molecules. His creativity and incredible productivity enabled him to develop new strategies to conquer nature’s most challenging, beautiful and seemingly unattainable compounds. One of those compounds was the anti-cancer drug Taxol. Listed on the WHO’s List of Essential Medicines (World Health Organisation, 2019), Taxol was first isolated from the Pacific Yew tree in 1971. When tested, Taxol showed enormous potential as an anti-cancer agent. However, due to the limited supply of suitable Pacific Yew Trees, there was a need to prepare ‘synthetic’ Taxol. More than that however, the enormous academic challenge of synthesising Taxol ‘from scratch’ appealed to the world-leading synthesis groups. Not without its bravado, a hugely competitive race to furnish Taxol began. After years of extensive efforts, the research groups of K. C. Nicolaou and Robert Holton (Figure 2) succeeded in synthesising Taxol in 1993 (Borman, 1994). One of the most complex molecules ever synthesised by ‘human hands’, Robert Holton emerged as the ‘winner’ by a ‘nose’ in a photo finish, as reported in the New York Times (Blakeslee, 1994). This was by a mere fact that Holton’s article was the first to be accepted for publication in the Journal of the American Chemical Society (Holton et al., 1994a). However, Nicolaou’s article appeared first in print in Nature (Nicolaou et al., 1994), one week ahead of Holton’s paper.

Figure 2:

Robert Holton (courtesy of Florida State University).

In parallel, a commercially viable preparation of significant amounts of Taxol was required for testing and ultimately clinical treatment. Again, it was Holton’s talent that surfaced, to achieve the semi-synthesis of Taxol, which made the large-scale production of Taxol possible. Holton’s group developed a four-step procedure for converting 10-deacetylbaccatin (isolated from the needles of the English Yew shrub, which in contrast to the Pacific Yew, was a sustainable source) to Taxol in high yield. Holton and Florida State University sold the patent to Bristol Myers Squibb for a reported $350 million. Holton’s personal share was a significant proportion! (Stephen, 2015). Sales of Taxol reached an astounding $1.6 billion dollars in 2000 Holton epitomise. Stories of Robert Woodward, K. C. Nicolaou and Robert Holton epitomise the excitement and real-life benefits a career in total synthesis can provide. One of the authors of this paper (GMG) was a Molecular Design and Synthesis Postdoctoral Fellow at Florida State University with Prof Holton. Regaling life as a postdoc with Prof Holton served to outline an achievable career pathway for the students, into the best laboratories in the world.

Influential contemporary researchers

Students noticed and were particularly inspired by the change in the nature of the contributors in synthesis from mainly older men in the mid to late 20th century, to a more gender and age balanced set in the last few decades. Phil Baran, Christina White and Melanie Sanford were highlighted during the lecture. This was a personal choice of this Author, but certainly all three chemists display/exhibit creativity, resilience, flamboyance, ambition, passion, integrity, hard work and the ability to use setbacks they experienced as learning experiences. It was hoped/believed that these personal traits would appeal to many students. Thus, the story of one of the most outstanding young synthetic chemists of our generation resonated with the students. Phil Baran’s (Figure 3) passion for chemistry began when he was an undergraduate at NYU. He describes his initial interaction as ‘love at first sight’ (Baran & Zbikowski, 2017; Peplow, 2014). Phil Baran (Figure 3) believes that to be a successful organic chemist, one requires ‘intense dedication, passion, and a positive aptitude; they also need internal optimism, intellectual humility, and a desire to create’ and he sees ‘failure as the currency of experience.’ (Baran & Zbikowski, 2017). By gaining an insight into the character/philosophy of the person, students become invested. In fact, any information surrounding the individual teacher and their broader interests paves the way for student engagement. Baran does an outstanding job at reaching out to his students across a number of platforms, including Youtube. He often post videos of himself carrying out the chemical reactions, and his fun rivalry with Prof Jin-Quan Yu (another trailblazer and leader in the field of organic synthesis) and battles in drag racing (Ikaworldwide, 2017a) and arm wrestling (Ikaworldwide, 2017b) are well known.

Figure 3:

Phil Baran (produced with permission from Prof. Phil Baran, https://syntheticremarks.com/slow-down-phil/).

It also proved critically important to highlight the significant contributions of the many female organic chemists over the last couple of decades. Providing inspiration to young female students is of upmost importance if we want to inspire a new generation of female organic chemists in the future (Sanford et al., 2020). Thus, outlining the career paths and interests of people like Christina White and Melanie Sanford sparked student attention. It is hoped that this may have a lasting impact on their future engagement in lectures, as well as providing inspiration and promise for women entering the field of organic synthesis.

Prof Christina White (Figure 4) was born in Athens, Greece and was the first woman to receive the ACS award for ‘creative work in synthetic organic chemistry’. Christina White takes inspiration from watching professional sport and views the ability to overcome obstacles and achieve goals in real time as fascinating (Kramer, 2019). Prof White visited UCC in 2014 and a number of undergraduate students attended. Again, current students start to see an overlap of their studies, and those in some of the world-leading laboratories. Another world-leader in organic chemistry is Prof Melanie Sanford. Surprisingly, as a young chemist, she was initially rejected by her preferred PhD supervisor, so she joined another group ‘When I started at Caltech, I wanted to get into a particular group. The professor said he didn’t have any space even though he took two other students that year. It was clear that he just didn’t want me, so I joined another group’ (Chapman, 2017). Thus, despite this perceived set-back, Sanford forged her way, ultimately to a MacArthur Fellowship, commonly known as the ‘Genius Grant’.

Figure 4:

Christina White (produced with permission from Prof. Christina White).

Sanford was also an excellent gymnast, she used the setbacks she experienced as motivation to succeed ‘When I was a kid I kept breaking bones: I broke my ankle and I broke my foot. When you break a lower extremity the only thing you can do is bars – as long as you don’t dismount or fall you can still swing on the bars. I spent a year and a half when I couldn’t land on my feet, so I got really good.’ ‘I was not particularly naturally talented, so I had to work 10 times as hard as others’ (Chapman, 2017). Here students gain an insight in the trials and tribulations of even the most talented, and what it takes to succeed.

Data analysis

The analysis of the data drew upon thematic coding methods (Braun & Clarke, 2006). As noted by McCauley and McHugh (2021), thematic methods are valuable when looking to identify patterns within data. A deductive approach to coding was adopted and while data is presented in a linear fashion below, analysis is a fluctuating stage of research. The codes move through varying levels of abstraction with a progression to higher levels of interpretation (Fereday & Muir-Cochrane, 2006). Coding was conducted using NVivo 12.6. The precise coding method can be described as ‘elemental’. Such methods include the use of descriptive, process and in vivo codes (Saldaña, 2012). This approach provides for an open analysis and enables the researcher to lift and place codes into categories and subcategories. This led to the development of patterns and themes which provides the foundation for the results of this study.

Data analysis

From the first two questions, 100% of students stated that they enjoyed the lecture and 100% of students felt that the lecture succeeded in grabbing their attention. The first qualitative question had a binary aspect and asked students if the first lecture was interesting (Yes/No) with a space for them to explain if they responded ‘No’. With a ‘Yes’ response, students were asked to fill out three more exploratory questions. All respondents indicated ‘Yes’ and we explore the pertinent themes below.

Emergent in the data was the theme of possibility in the field of organic synthesis. Students recorded their excitement given that there is ‘so much to discover’ in the space. This was linked to the idea of career progression and opportunity in a domain where findings are ‘relatively recent’. One student noted that they enjoyed the lecture as they had the opportunity to …

“See and hear recent advances while still being room for new developments”.