Ever since Dr. Bill Bailey was a young child, he knew he wanted to teach. Now, looking back on a 45-year career of teaching and service, Bill embarks on a new chapter: retirement.
A Journey: From Plumbing to Teaching
Growing up, Bill was destined to become a plumber. Bill’s father and grandfather were plumbers, and his father owned a plumbing shop in their hometown of Jersey City, New Jersey. Although Bill had also earned his plumbing license, his true passion always lied in teaching.
Bill pursued a Bachelor’s Degree in Chemistry at St. Peter’s College in Jersey City. There, in a class of Chemistry majors, new Assistant Professor James Pegolotti explained that it was possible to go to graduate school for free and to be paid a stipend. Bill credits Dr. Pegolotti for instilling the confidence in him to apply to graduate school: “It’s a remarkable thing. … Jim Pegolotti is the one that explained that such a thing was possible. Otherwise, I wouldn’t be here [at UConn teaching].”
Bill then went on to attain a Ph.D. in Chemistry at the University of Notre Dame with Professor Ernest Eliel. Bill’s Ph.D. work involved investigations of the generalized anomeric effect and the stereochemical dependence of 13C shifts. After receiving his Ph.D. from Notre Dame in 1973, he accompanied Ernest to the University of North Carolina where he helped with the set-up of the newly built labs. Bill then departed for a postdoctoral fellowship with Professor Kenneth Wiberg at Yale University.
In 1975, Bill joined the faculty at the University of Connecticut. Bill reflects, “[Professor Emeritus] Jim Bobbitt … was the one that was head of the search committee and he was the one that convinced me that this would be a wonderful place.” Dr. Jim Bobbitt describes the moment he extended the offer: “I placed a telephone call to Bill Bailey at Yale to offer him a position on our faculty. He accepted, and that was a very good day for the University of Connecticut.”
45 Years of Teaching
Over a 45-year teaching career at UConn, Dr. Bill Bailey has instructed over 8,000 undergraduate students and approximately 600 graduate students. Since 1975, Bill has primarily specialized in teaching organic chemistry courses. When teaching traditionally challenging material, Bill advises: “The secret is somehow you have to convince the students that they can really master this, and that’s it’s not as bad as they think. You have to be more like a coach than a teacher; you have to encourage them, but challenge them.”
“I try to make the course challenging, and most students rise to the occasion. You have to cut them a break, and tell jokes, and stories,” Bill explains. “I never decided, ‘This is how I’m going to do it,’ but I did rewrite my lecture notes every single year … and if you rewrite them every year, you never really need notes: you can come in the next morning and teach the course. It’s always been fun. I never thought of it as a job. At all.”
Current and former students have responded positively to Bill’s teaching approach. Physiology and Neurobiology undergraduate student Hanna Englander ’21 (CLAS) took Dr. Bailey’s Organic Chemistry 1 and 2 courses during her sophomore year. Now a senior, Hanna reflects, “I never anticipated that chemistry would come to be one of my favorite courses, but it truly was and I have Dr. Bailey’s amazing teaching to thank for that. Dr. Bailey taught this course in such a way that he really sought out to make student’s believe in their capabilities. … He was able to instill such an enormous amount of confidence in his students which is so immensely valuable when trying to navigate your way through a difficult major. … After an entire year with Dr. Bailey, I was able to grow confidence in my abilities and also uncover a passion for the study of chemistry.”
Chemistry Alumnus Sherif Eldirany (CLAS ’16) echoes, “In my 21 years of school, Dr. Bailey is the single greatest educator I have had the privilege of knowing. Dr. Bailey's passion for organic chemistry and genuine interest in his students made my experiences in his classroom and research lab the highlights of my undergraduate career.”
Honors Organic Chemistry
Since 2000, Bill has taught over 1,200 Honors students within Organic Chemistry 1, Organic Chemistry 2, and Honors thesis courses.
In recognition of his teaching, Dr. Bailey was selected as the Honors Faculty Member of the Year in 2011. When asked to describe Dr. Bailey, one nominator shared, “He turned a subject that is both very challenging and … very dry and tedious, into one which pushed me academically, but also made me excited to come to class.” Another nominator said, “He teaches us the material, but also gives us the context for discovery.” Dr. Jennifer Lease Butts, Associate Vice Provost for Enrichment Programs and Director of the Honors Program, notes, “There is no greater legacy for an educator than to spur discovery, creativity, and innovation in students, and Dr. Bailey did this repeatedly throughout his illustrious career at UConn.”
Bill also worked to include upper division Honors students as undergraduate teaching assistants in Honors Organic. “In doing this, he created a supportive environment bolstered by peer interactions,” notes Dr. Lease Butts. “The students in the class gained immensely from having older chemistry students to turn to … [and] the Honors teaching assistants developed skills in teaching, mentoring, and service. I know students who served in this role have continued on to Ph.D. programs with hopes for a career in academia, and the positive experience in this role — where they also were mentored by Dr. Bailey — is one of the things they cited as inspiring their future plans.”
Research Impact
Although Bill jokes that grant-writing is a task that he would prefer to do without, his passion for research is clear: “I always thought that research was like a hobby. It was a lot of fun. … When you’re there when someone figures something out of importance that nobody else in the world knows at that moment, that really feels good.”
Bill’s research interests lie in the development of new synthetic methodology using main group organometallic chemistry, the investigation of reaction mechanisms, and molecular structure and energetics. Bill is perhaps best known for the development of intramolecular carbolithiation as a route to functionalized ring systems. His 1985 report, detailing the kinetics of the cyclization of 5-hexenyllithium to (cyclopentyl)methyllithium, was the first unequivocal demonstration of the intramolecular addition of a C–Li bond to an unactivated carbon-carbon π-bond. Prior to Bill’s work in this area, the extensive literature dealing with the mechanism of the exchange was difficult to interpret and the preparation of simple organolithiums by the exchange method was more of an art than a science (Juaristi, ARKIVOC).
Creating Connections
However, despite his research achievements, Bill is quick to redirect the credit and focus to his students. “I’ve been very lucky,” Bill says. “I’ve had incredibly good, incredibly talented students over the years. … It all comes down to how talented and how hard-working your graduate students are, and how well you interact with them. I’ve had really talented graduate students who are really nice people. … It’s been lovely.”
In speaking with Bill, he then goes on to tell stories about his former students who now have successful careers in academia, industry, medicine, and business. He also tells stories about former students who have experienced recent milestones like a new baby or their own retirement. Bill also tells the story of how a father and son worked in his lab, 30 years apart. His pride and care for his alumni punctuate each element of the conversation.
“I put in a lot of time to try to make a connection with students. I think that’s really important. If you look back … the people that had the most influence on you were professors you got to know a little better … of whom you would ask for advice and guidance. I’ve always cherished that when students would come into my office and chat and talk and complain,” Bill says.
As Bill retires, he reflects that the proudest moments in his career have been when he’s received emails or letters from former students: “I love to hear from former students. That’s what makes me really happy. … I know that once they’ve left, there’s no reason for them to butter me up to get a good grade. … That’s the best part.”
Student Guidance
Much of the Bailey Group’s success can be attributed to allowing each other to learn from mistakes: “They’re making their own mistakes and learning from them, just like in real life. You do something, you do it wrong, and you go, ‘I won’t do that again!’.”
Bill also believes in not making demands of his students. “There’s no point in trying to force people to do something they don’t want to do, because they don’t do it well. … Everybody goes through this valley where they think … ‘Nothing’s going to work out. This is awful. There is no end in sight. Nothing’s working. I’m tired.’ The only time I’ve guided students is when they’ve been in this deep valley and they don’t think that there’s any way out, but there’s always a way out. … I don’t force them to do things they don’t want to do. And most of them … know more about their project when they finish than I do, and that’s what you want: you want them to be the expert.”
Retirement
Although Bill says that he will miss the students, colleagues, and staff, he looks forward to enjoying his retirement. Despite the pandemic temporarily changing his plans, Bill has been working on projects around the house and taking walks with his recently-adopted dog, Ollie.
When COVID-19 restrictions lift, Bill plans to volunteer at a local library and spend time traveling. Specifically, he hopes to return to Australia, where he spent 6 months on sabbatical at Flinders University of South Australia in 1991.