How To Do Well In Organic Chemistry: Advice From A Tutor

This is a guest post from Anna Tsimelzon, Ph.D., a university organic chemistry instructor and private organic chemistry tutor. You can learn more about Anna’s tutoring services on her website, Tear Free Chemistry. 

My name is Anna Tsimelzon and I have been a private chemistry tutor for the past 5 years. I hold a Ph.D. in organic chemistry and I also taught Organic Chemistry at university level. I have tutored over 100 students in organic chemistry 1 and organic chemistry 2 from universities and community colleges all over the country.

Here are my tips on how to do well in organic chemistry.

1. Focus On Problem-Solving

I am not going to state the obvious, such as go to lecture, take notes, do homework and so on. These are just plain good study habits. Unfortunately, even students with good study habits quite often struggle with organic chemistry.

I can’t tell you how many times I heard from my students: “I study every day for 2 hrs, I read the textbook twice, and I am barely pulling a C!”

My heart goes out to these hard working students, but it is not enough to study hard. The key is to study smart. Organic chemistry is about problem solving. Two thirds of your study time should be spent doing problems, not reading the textbook.

Imagine that you are learning how to drive a car. If you read the car manual cover to cover it does not mean you know how to drive! In order to learn how to drive you need to get behind the wheel.

The same approach should be used to study organic chemistry. Problems, problems, problems!

2. Understand what your professor expects from you

Many students complain to me that the exams are much harder than homework. This is especially true for those students who have online homework, which is way easier than a typical exam. It is very important to understand the requirements of your specific course at your school. The best way is to get ahold of the old exams from your professor or from another professor at your university teaching the same course.

If the old exams are not available, then search for old exams online. 

Many universities in the US have open online courses that are free of charge. The two links below contain exams from MIT and Harvard. These are more on the challenging side.

• https://ocw.mit.edu/courses/chemistry/5-12-organic-chemistry-i-spring-2005/exams/
• https://canvas.harvard.edu/courses/571/pages/practice-examinations

The next link provides collection of old exams for both orgo 1 and orgo 2 from universities all over the country. The exams are ranked as easy, medium and hard.

• http://www.aceorganicchem.com/organic-chemistry-practice-exams.html

3. Prepare For Three Common Types Of Exam Problems

The typical organic chemistry exam will consist of problems of three types:

1. fill in the blanks (i.e. fill in the reagents or the products in the reaction scheme);
2. mechanism;
3. synthesis

Here are my study strategies for each type of problems that you will encounter in the typical exam.

Filling In The Blanks:

Here is an example of exercise that I do with many of my students:

Fill in the missing reagents in the following reaction:

I ask students to compare the starting material and the product.

• What bonds were destroyed? C-H.
• What bonds were formed? C-Br and H-Br.

Once you list the bonds that were broken and the bonds that were formed it becomes easier to figure out the reagent.

• What was the source of bromine, that was added to the aromatic ring? Br₂
• Br₂ will not react with benzene without a catalyst, as benzene is very unreactive. What was the catalyst? FeBr₃

How does the catalyst work? It acts as Lewis acid.

By asking these questions I am directing student towards understanding of the process rather than just regurgitate the information.

At the end of each chapter, there is a summary of all the reactions covered. I would do the above exercise for each reaction studied.

Mechanisms

After each chapter in any organic chemistry textbook there is a summary of all the reactions. The student needs to be able to draw the arrow pushing mechanisms for all of the reactions.

When studying mechanisms, identify the newly formed bonds, just like you did when preparing for fill in the blanks questions. New bonds are formed between atoms that are electron rich and atoms that are electron poor. For each mechanism the student has to be able to identify these atoms. Once the student has this figured out drawing the correct arrows becomes piece of cake.

Synthesis

Doing synthesis problems is the best way to review all the reactions studied previously.

One of the things that many students do not realize is that in organic chemistry everything is connected. If you studied epoxides last semester, it does not mean you can forget about it after the exam. It will come back to haunt you in the next semester.

Synthesis problems are like comprehensive reviews. While doing synthesis problems you are preparing for fill in the blank questions, where you need to provide the missing reagent or the product.

For each functional group I would make an index card on how to synthesize it.

On the front it will say “ways of making alcohols”, for example.

On the back, I would list all reactions that allow you to make alcohols.

Have the stack of these index card on hand while doing synthesis problems. If you do enough synthesis problems, eventually you will stop relying on index cards and will naturally remember all the reactions.

Conclusion

I wish I could say that if you will be following all of these instructions you are guaranteed an “A”. Unfortunately, that is not true, as organic chemistry is a challenging subject.

But I can promise you one thing: you will get better at organic chemistry!

There will come a day when all of a sudden you will hear a penny drop: it finally makes sense!

Anna Tsimelzon, Ph.D. is a private organic chemistry tutor and has taught Organic Chemistry at American colleges and universities. You can learn more about Anna’s tutoring at her website,  Tear Free Chemistry