Challenges faced by students in Retrosynthesis in organic chemistry.

-Introduction: What is organic chemistry? What is Retrosynthesis? The role of Retrosynthesis in organic
chemistry.
- Major Challenges faced by students are , in no particular order , Fundamental understanding of basic
reaction chemistry. Understanding how mechanisms work , ie. group of attack , the roles of arrows ,
feasibility of a reaction.
- Teaching styles by teachers , ie, writing on board and explaining might not be the best teaching
approach for all the students. Also it should be notes that as it is taught , retrosynthesis seems to be taught
in the same way for decades now , that is as stated earlier.
- Students find it difficult to remember the reagents , reactants and respective functions of these chemicals
, they can sometimes be overwhelmed by the number of reagents and reaction conditions to learn.
-Long reaction mechanisms can confuse students , also students can sometimes be intimidated by the
complexity of elaborate compounds.
-Students underestimate the course.
Snowball Nature of Retrosynthesis , ie the teacher keeps building on ideas and if u get left behind early it
becomes difficult to catch up.

18/10/2014
ANDRE RATTANSINGH
812000478
CHEM 2770 : Intro to Research ChemLearning
Expository Essay #1
Challenges Faced by Students in Retrosynthesis for Organic Chemistry.

This essay deals with the question What challenges do students face when doing
retrosynthesis for organic chemistry? This questions peeks my interest as I was a student in an
advanced organic chemistry class in my second year, where the main emphasis of the course was
retrosynthesis , the challenges faced by my peers and I should therefore be explored and placed
into context since these challenges cannot be overcome until they are first identified. It is with
this frame of mind that this piece is done, hence its value can be stated as being important to any
student in the chemical field involved in doing retrosynthesis and can also help them to identify
said challenges and take appropriate steps to overcome them.
Organic chemistry is a fascinating subset of chemical topics , it deals with the chemistry of
natural compounds , that is , carbon compounds , such as methane , the simplest of the organic
molecules. Retrosynthesis is an organic chemistry topic and deals with the breakdown and resynthesis of organic compounds , it has many uses , but perhaps its main use is in creating
reactions pathways to produce a desired compound , for example , benzacaine , paracetamol ,
certain pesticides , and pain killers can all be retrosynthesised and produced via known chemical
pathways. This is the beauty of retrosynthesis , it allows the chemist to create elaborate
compounds using known chemistry. To a student however this particular topic can be daunting
and at times, overwhelming , since, as will be discussed in this essay , there are numerous
challenges that a student may face when doing retrosynthesis , these taken from my own
experience, that of my peers, as well as those stated in literature.
One of the major challenges in retrosynthesis is that students do not possess the proper
understanding of the fundamental or basic concepts in chemistry , such concepts as bonding ,
addition and substitution reactions, electrophillic and nucleophillic reactions still give students
problems. This gap in understanding becomes even larger when the basics are used by the
teacher to create more complex concepts , an example of this can be seen with the topic of
reduction , if a student doesnt already understand this properly , then when the teacher discusses
how it can be used in synthesis , such as converting a nitro group into an amino group by
reducing with hydrogen gas and a platinum electrode, the student is even more perplexed. It can
be said therefore, that for a student to be able to do well in retrosynthesis , they must first have a
good working understand of fundamental chemical concepts , so that when these basics are used
to build more complex models , the student can more easily bridge the learning transition.

Another major challenge faced by students in retrosynthesis ,as stated by (ODwyer and
Childs 2001), together with students from my class, is the difficulty in understanding how
mechanisms work . Mechanisms are chemical representations of how bonds are broken and
reformed in a particular reaction, they emphasize the movement of electrons through the use of
arrows. The term attack is often used when dealing with reaction mechanisms , it refers to how
particular groups take atoms or substituents from other groups. The group being attacked is
usually electron deficient and the group doing the attacking usually gives over an electron. This
concept of attack can sometimes puzzle students as some do not fully understand which group is
attacking or being attacked. Hence, this problem becomes amplified when dealing with large
complicated structures as is the case with retrosynthesis. An example of this type of problem was
evident to me when the class received a tutorial question which involved retrosynthesising the
structure of paracetamol , this was a six step process and hence involved six separate reaction
mechanisms and led to many students becoming bewildered as the steps involved attacking
functional groups , this left the greater part of the class without an answer to the question , most
simply leaving the question blank on their tutorial sheets. In retrospect ,a possible solution to the
problem would have been to read relevant textbooks or online resources and re-learn
electrophillic and nucleophillic attack , however at the time, this was not done since most of the
students simply were not aware this was the problem they were having. This re-emphasizes the
importance of identifying these problems so that they can be overcome in time.
Building on the last point made, with respect to mechanisms , the use or arrows in reactions
are another major source of pain towards retrosynthesis by students. Arrows are used in reaction
mechanisms to show movement of electrons , and as stated before it shows which group is
attacking which, but more importantly it shows how these groups form new bonds or even to
break old bonds. Pushing arrows is extremely important in retrosynthesis as it depicts the
mode of action of reactants , that is , how they break/create bonds to shape the starting reactants
into the all important final product . Hence without this understanding, students will have great
difficulty in more complex reactions where more than one bond formation and bond breaking is
taking place.
(Davis 2006) states that the feasibility of a reaction is also a challenge that students face ,
that is , understanding which reactions will work and which ones will not. This is usually worked

out by energy calculations, for a reaction to be feasible the product must be of lower energy than
the starting reactants , meaning that the product is more stable, this is important as it allows
students to understand what reactants can be used to make the desired product. However in
retrochemistry , the student isnt given values to calculate, it therefore means that they must have
a working knowledge of which reactions are possible and which are not. A very frequent
example of this is seen when a question asks students to synthesise a compound such as
bromobenzene , this was also asked as a tutorial question and a lot of the students unknowingly
stated the answer as add Br2 however , someone with a working knowledge of this would
understand that because of the relative stability of benzene , it will not brominate under standard
conditions , hence a catalyst is needed , the catalyst taught to us was AlBr3 , this forms a
bromonium ion capable of adding to the benzene , creating the desired product. There is not an
easy way of overcoming this challenge it seems, other than simply learning all the reactions
required for the particular course and practicing as many problems as possible so that the
reaction mechanisms , and their feasibilities are second nature.
Another challenge that is faced by students is the teaching styles of the lecturers.
Retrosynthesis has seemingly been taught the same way for decades , whereby the teacher comes
to class, writes out a reaction mechanism on the board and then goes through the mechanism step
by step , for me, this was easy enough to follow , as long I took notes of everything that was
written, I was always able to keep up. However the experiences of my peers were not as
encouraging, they found that this particular teaching style did not suite them. It is known from
cognitive science that people process information differently , so while the teaching style may
have been ideal for me , it could have come off as monotone and difficult to follow for others.
The fact that some students do not take sufficient notes also adds to this problem ,since a vast
number of the students finding difficulty with the lectures were often the ones who did not have
proper notes , meaning that if they could not comprehend a particular lesson during the lecture,
then they would not be able to go over the concept afterwards. Adding to this is the fact that no
online slides are released for this particular topic. While I understand that everyone learns in
different ways, I still believe that with respect to this particular challenge, taking proper notes
will give a student the best chance at understanding the concepts, regardless of the teaching style.

Many students have difficulty in perfoming retrosynthesis questions when exposed to

complicated looking structures and compounds. This particular challenge is solely based on the
perspective of the student , however most students agree that there is feeling of anxiety when
they see a question with an elaborate structure. This can be due to students becoming intimidated
by the question and thinking it is harder than it actually is. I personally had this problem ,
whereby when I would see a large interconnected structure I would become intimidated and not
know where to start , this feeling can sometimes make students flustered and forget their
chemistry knowledge. It is important to practice such problems before hand, this is how I got
over this problem ,by working as many complicated retrosynthesis problems as I could find , this
makes it easier when you see such a structure in an exam , you understand what steps you need
to take to approach the question and overall it makes the entire experience less stressful.
One particular challenge that is not readily evident is that students can sometimes
underestimate the course. This can occur because a lot of times retrosynthesis lectures begin the
first couple of weeks by going over simple concepts and doing very basic examples on the board
, this can put the students in a false sense of security since they do not fully appreciate how
complex and difficult the topics would soon become. The very nature of the course lends itself to
being underestimated, students comes to class and follow along as the teacher writes down the
correct approaches to synthesising a compound and it all looks very organised and simple to
them. The wrong assumption that students make here is that they equate the ability to follow
what the teacher is doing with their own ability to do the very same task , understanding is half
the battle , but being able to reproduce what you have seen is imperative. This was evident to me
by the comments of my peers towards retrochemistry as it progressed through the semester , at
the start , most people found it to be easy , interesting , and overall quite doable , however as the
semester progressed most students had a completely different outlook ,most claiming to be
perplexed and lost. It is therefore a topic that deserves respect and cannot be underestimated.
The most frequently stated challenge students face in retrosynthesis and also the one which
personally gave me the most difficulty was , remembering all of the reagents , their reaction
conditions and what function they actually carried out. Retrosynthesis involves synthesising
compounds using known chemistry , the term known chemistry in this case refers to the
reactants and reagents being used , therefore this can be said to be one of the most important

aspects of retrochemistry since if a student does not know these chemicals then they will not be
able to produce a correct synthesis plan. The reagents and their conditions are used to create the
desired compound , for example , if a student was asked to add a nitro group to phenol , then the
student would need to know that nitro groups are added to a benzene structure by using sulphuric
acid , coupled with nitric acid , however if the student does not know this information then they
cannot perform or indeed proceed to the next logical step in the synthesis. The number of
reagents that a student is required to learn may seem large, however there is a set amount stated
in the course outline and is in actuality not that many. That being said the student still needs to
learn all of them. One way I overcame this problem was to prepare a reagents sheet, that is a list
of all the reagents and functions, this made the task of performing retrosynthesis much easier
since I already had all the knowledge of the reactants and all I needed to do was simply apply
this knowledge to the particular problem.
In conclusion, it is apparent to me that retrosynthesis is a topic that gives students difficulty
because of the very snowball nature of the topic in which concepts are built upon, becoming
more and more difficult as the course goes on , the topic starts out using simple ideas and
concepts and ties in pre-requisite knowledge in the first weeks but then ideas becomes very
complicated , in some cases involving five and six step reaction mechanisms and requiring the
student to have a working knowledge of ten or so detailed types of reactions. Hence any problem
the student is having with understanding becomes magnified as the course progresses. This
means that if at any point the student becomes lost in the course it is very difficult to catch back
up , and the fact that the topic uses a lot of fundamentals in chemistry , if the student doesnt
understand the basics well, they can become lost even earlier. It is imperative that the student
must keep up with the course , reviewing material from lectures , making sure to understand all
examples , reading ahead when possible and most importantly, addressing any difficulties
immediately, before they become a noticeable problem. Retrosynthesis is indeed a very
interesting and rewarding topic to learn but requires a lot of groundwork and should be
approached with an attitude of utmost diligence.

References
(1) Davis, G. Investigation of most difficult Organic Chemistry Topics for Senior Secondary
School students and teachers in the Central Region of Ghana
https://www.academia.edu/8314878/Investigation_of_most_difficult_Organic_Chemistry_
Topics_for_Senior_Secondary_School_students_and_teachers_in_the_Central_Region_of_
Ghana (accessed Oct 21, 2014).
(2) O'Dwyer, A.; Childs, P. Second Level Irish Student's and Teacher's View of Difficulties in
Organic Chemistry http://www.esera.org/media/ebook/strand10/ebook-esera2011_odwyer10.pdf (accessed Oct 21, 2014).
(3) Zoller, U. Students Misunderstandings and Misconceptions in College Freshman Chemistry
(General and Organic) http://onlinelibrary.wiley.com/doi/10.1002/tea.3660271011/pdf
(accessed Oct 21, 2014).
(4) Schaller, C.; Graham, K.; Jones, T. J. Synthesis Road Map Problems in Organic Chemistry
Chem. Educ. 2014, 141016062937009.
(5) Vosburg, D. J. Teaching Organic Synthesis: A Comparative Case Study Approach
Chem. Educ. 2008, 85, 1519.
(6) Kayala, M.; Azencott, C.; Chen, J.; Baldi, P. Learning to Predict Chemical Reactions
Journal of Chemical Information and Modeling 2011, 51, 2209-2222.