CHEM 233: A Student’s Guide to Studying Organic Chemistry by Amber Richardson is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International LicenseTo view a copy of this license, visit http://creativecommons.org/licenses/by-nc-sa/4.0/.

Welcome to CHEM 233’s Study Strategies Workshop! Feeling overwhelmed by the electrons, carbons, alkenes, alkynes, isomers and more? Have no fear, study strategies for you are here! We hope that this guide will help you learn some new and very effective ways of studying organic chemistry. These strategies require self-reflection, dedication, effort, patience and practice. We hope that if you use them for this course, you will increase your understanding of the concepts in CHEM 233 and be able to achieve more and appreciate the wonders of organic chemistry!

Contents of Study Strategies Guide: Page 3: Flashcards Page 5: Summary Notes Page 7: Elaboration Page 9: Concept Maps Page 11: Practice Problems Page 12: Study Groups Page 13: Preparing for Lectures Page 14: Resources and Workshop #2 Assignment

Why flashcards? Flashcards are proven to be very effective for memorization (Din & Wienke, 2001). In organic chemistry, flashcards are useful for:

x Vocabulary x Basic reaction schemes x pKa’s x Generic chemical formula

Flashcards can also be useful to study in combination with elaboration technique (see pages 8-9). How to use flashcards Use flashcards to quiz yourself! It is a good idea to make both sides form a question in your mind with the corresponding answer on the back. In other words, don’t make a “front and back”;; there should be two questions with two answers. For example, a definition vocabulary card should have the term on one side and the definition on the back (the definition should not contain the term) so you can either look at the term and give the definition, or look at the definition and give the term. Flashcards are most effective if used consistently and as one large stack (Kornell, 2009). Separating the flashcards into smaller piles won’t be as helpful. It is also very important to shuffle your flashcards so you actually learn them individually rather than memorize them based on the order. Make flash cards after class and study them daily for short periods of time rather than waiting until the last minute and cramming all of them at once. (need to add to study guide). Studies have shown that you should not “drop” flashcards you have learned. If you keep testing yourself, you will remember the content for longer. Note of caution about flashcards!! Memorization is the most basic level of studying and should only be used for ideas that need to be memorized (things you will be tested on at a basic level, or fundamental concepts that you will need to know to understand more challenging ideas later). DO NOT TRY TO MEMORIZE EVERY REACTION THAT YOU SEE IN THE COURSE. Use flashcards to write out general reaction schemes and why they happen, but do not use them to write out specific reactions. There are too many reactions in the course to try to memorize them all. It’s better (and much easier) to understand why types of reactions occur and learn how to decide which reaction type occurs when given specific chemical species.

Kornell, N. Optimising Learning Using Flashcards: Spacing Is More Effective Than Cramming. Appl. Cognit. Psychol. 2009, 23, 1297-1317. Din, F., Wienke, E. The Effects of Flash Card Us on Students’ Comprehension of Chemistry Vocabu-­lary. ED 458 115;; US. Dept. of Educ: Illionois, 2001.

Flashcards

Examples of Flashcards:

Things to note about flashcards: x No “front” and “back” - could make a question from both sides

x For reaction, only the general form, not an exact example of a reaction (too many reactions to memorize!!)

x For the definition, only one side contains the vocabulary term, not both sides

Why make summary notes? Summary notes are a good way to see how much you understood from readings and lectures. The more you can write in a summary, the more you likely understand and can better retain a concept from your memory (King, 1992;; Dyer, Riley & Yekovich, 1979). If you do summary notes but find you are struggling with summarizing, it means you need to spend more time on that topic. When to write summary notes? Studies show that comprehension increases when summary notes are written after a delay from reading texts or from lectures (Thiede & Anderson, 2003). When doing summary notes from a textbook, summarize at the end of your readings rather than after each small section (e.g. summary notes for all of Chapter 18 rather than for section 18.1, 18.2, etc.). For lectures, it’s best to do summary notes at the end of each topic. Doing them after each lecture may be good, but you may revisit topics from previous lectures that would be good to add to the summary. When writing summary notes, try to write them from your own memory. How detailed should summary notes be? Summary notes should be detailed enough for you to be able to study directly from them. Highlight key terms, definitions, reactions, mechanisms, etc. but do not make them so de-­tailed that you have extra content that isn’t necessary! Writing summary notes in point form is often a good way to write concepts in your own words and keep out excess terms. A summary of summary notes!

x Struggle with summarizing concepts = spend more time studying that topic x Make summaries at end of textbook chapters/lessons in lectures, not end

of small sections x Include key terms, reactions, definitions, and mechanisms. They should be useful to

study from!

Summary Notes

King, A. Comparison of Self-Questions, Summarizing, and Notetaking-Review as Strategies for Learning From Lec-­tures. Am. Educ. Res. J. 1992, 29, 303-323. Dyer, J., Riley, J., Yekovich, F. An Analysis of Three Study Skills: Notetaking, Summarizing, and Rereading. J. Educ. Res. 1979, 73, 3-7. Thiede, K., Anderson, M. Summarizing can improve metacomprehension accuracy. Contemp. Educ. Psychol. 2003, 28, 129-160.

Example Of Summary Notes: In text, highlight:

x Key terms

x Definitions

x Reaction schemes

x Mechanisms

x Properties of compounds and types of reactions

In summary notes:

x Use point form

x Make key terms stand out with colours

x Include diagrams and arrow pushing mechanisms

x Put examples

x Leave room to add more notes as you study

What is elaboration? Elaboration is essentially the opposite of summarizing. Instead of summarizing con-­cepts from readings or lectures, you write down as much as you possibly can about a reaction, term, or concept. When to do elaboration? Elaboration is most useful to see how much you know. Elaboration that involves re-­trieving the reactions, terms, or concepts from your own memory will also help with long-term memory (cite). Beginning your studying by writing down all that you know helps you see what topics you are confident in and those that you struggle with. This can help you focus your studying on topics that need more attention. How do to elaboration? You can either begin elaboration by looking at the learning objectives or at your reaction summaries/terminology from the course. The following points will apply to both. WITHOUT LOOKING AT YOUR NOTES OR TALKING TO PEERS, write down everything you can think of that relates to the concept you are elaborating. And by everything, I mean everything. Reaction schemes, examples, mechanisms, properties of the compounds involved, when the reactions occur, when they don’t occur, pKa values, vocabulary, etc. Once you have put down everything you know about the concept, then you can return to your notes to see what you are missing. If you are missing many of the key points, then you know that is a topic that you should study more rather than topics about which you are more knowledgeable. You can also employ the elaboration technique through flashcards and summary notes! Once you have filled in all the gaps about a particular concept (such as a reaction), put the reaction on one side of a flashcard and put the key points in a summarized and organized way on the back. This way you can do verbal elaboration alongside doing practice problems while studying for your next midterm.

Elaboration

Levin, J. Elaboration-Based Learning Strategies: Powerful Theory = Powerful Application. Contempt. Educ. Psy-­chol. 1988, 13, 191-205.

Example of Elaboration:

What is it missing?

x Aromatic ions

x Example of MO diagram showing decreased energy levels

Concept Maps

Here’s a quick summary of how concept maps work: x They contain connecting words between ideas that together represent concepts. x They start with one main idea and break it down into smaller elements, which are

often more interconnected. While the diagram says that the most specific concepts are the least important, in organic chemistry even the specific concepts are important to learn!

How to make concept maps Concept maps are used to summarize larger topics such as a class of reactions, aromaticity, isomerism, etc. Begin with the broad topic and then break it down into smaller pieces. You can use questions such as “why, where, when and how” to help guide you through connecting ideas. Bubbles should contain no more than a few words as the connecting words paired with the bubbles should form the “sentences”. When to make concept maps Concept maps can be used to track your knowledge of a topic. Start by making a concept map before you begin studying, to see how much you know. Once you have finished studying, you can make another concept map, to see how much more you have learned about that concept. Concept maps do take a lot of time to make, but they are beneficial. Studies have shown that consistently making concept maps allows students to make more effective concept maps and helps with their retention of concepts (Novak, 1990).

What is a concept map?

Novak, J. Concept maps and Vee diagrams: two metacognitive tools to facilitate meaningful learning. Instr. Sci. 1990, 19, 29-52.

Example of a Concept Map:

What is it missing?

x More examples—heterocycles, aromatic ions

x Resonance structures

x Can hybrid orbitals be in an aromatic compound?

How to do practice problems the right way: 1.Study before doing practice problems. Whether the practice problems are homework, online questions, extra practice from the textbook or for studying for a midterm, always review your notes and organize the course material in your head before you do the questions. However, you may want to start doing practice problems without reviewing your notes a few days before a test to ensure you have a more complete grasp on the subject. Pretend that every assignment you do is a test as midterms and fi-­nals aren’t open book! 2. Attempt all of the problems: 1. On your own, 2. Without the help of your notes (hence why you studied them first!), and 3. Without the answers. 3. Figure out what the question is asking before you do it. Is it asking for a mechanism? For the missing reagents? Find the relevant concepts in the question and use them to help you answer. 4. Employ self-explanation. That is, be able to explain why you did each step in a problem. If you are doing a mechanism, be able to explain why a pair of electrons moved from A to B and not C. For an SN2 reaction, be able to explain why there is no reaction in-­termediate like in SN1 reactions. If you can explain why every step happens, you under-­stand the material. 5.Once you have answered all of the questions and cannot add anything else to them, check your answers with a peer. Be able to defend your answers, ask questions about those that you understood less and work together to find solutions. 6. After you have added to your answers, compare your answers to the solutions. If your answer is wrong:

x Figure out WHY it is wrong. Do not just accept that it is wrong, learn from your mis-­takes by thinking about the question deeply

x Add to your notes/concept maps/reactions summary notes. Make note of what you missed so you can better understand why the answer is wrong and not make the same mistake in the future.

Keep track of the scores you get on problems to see if you are improving or not. If you are consistently making the same mistakes on the same problems, you will know what you should focus on. It is better to know what you don’t know and to improve on them instead of accepting defeat on a topic! When doing practice midterms or finals, treat them like they were the real exam. Do them on your own in a quiet area, without any notes, and timed to be the length of the ac-­tual exam. When done, mark them to give yourself a score, but also make note of areas that you struggled with that you could study more before the actual exam.

Practice Problems

Studying in groups can be very helpful for your understanding of the material, as long as you do it properly. Here are some tips to help you study effectively with your friends and peers! x Ask each other questions and debate answers. If you are working on practice

problems, do them individually then debate the answers BEFORE looking at the solutions. This way, you will have to rationalize why your answer is right, or why their answer is wrong;; if you can do this, you have a good understanding of that particular topic

x TEACH, don’t repeat. When someone asks you for help, do not just restate what the

questions/notes/textbook says, put your answer into your own words to help them. Break down concepts into smaller pieces so you can better explain why things occur. If you can teach a concept, you know that concept extremely well!

x Stay focused on the material! This may be the hardest part of studying with friends,

because we all know that episode of Game of Thrones was phenomenal and shocking, but during study time (sadly) isn’t the time to talk about it. A way around this is to have set study breaks every half hour for 5 minutes to give yourself a break. If you reach the half hour mark but are really focused on the work, keep going! Once you feel like you need and deserve a break, take it and enjoy it. But make sure you don’t take too long of a break!

x Be prepared. Go over the material and make sure you have done some practice

problems before you meet up. This way you can formulate questions that you want to ask your friends about. Another way is to decide what you want to cover before you meet, and each go over that topic individually before meeting so one of you isn’t further behind than the other.

Studying in Groups

Lazar, A. Who Is Studying in Groups and Why? Peer Collaboration Outside the Classroom. College Teaching. 1995, 2, 61-65.

Preparing for Lectures CHEM 233 is taught using an active learning approach which may be new to many of you. While it is new, it is meant to help you learn and understand the material better. Here are some tips on how to best prepare for lectures so you can make the most of your class time: Step 1: Video & Textbook

1. Watch the entire video without stopping it to get a grasp of the overall topic

2. Watch the video again, but this time PAUSE the video to take notes. Don’t try to take notes while they video is playing as you will miss important points that the instructor is mentioning

3. If you still struggle with the material after watching the video and taking notes, USE THE TEXTBOOK as well. Some students prefer reading to watching the videos, and some prefer the videos. Figure out what is most useful and motivating for you.

Step 2: Pre-class Preparation

1. Self-test - try to do the self-test on your own after going over the concepts in the videos/textbook.

2. With the instant feedback that you get back, you can then learn what concepts you understand and those that still need more explanation

3. Bridge Activity - try to do these questions on your own first, once again, to see what you know and don’t know. If you need to, use your notes to answer them

4. Don’t forget, you get participation marks for these because they will help you get ready for class!

Step 3: Summarize

x Before you go to lecture, make sure you can distinguish the three main points from the video and text (try for three main points for each topic)

x Formulate any questions that you have about the material that weren’t answered by the video or text

x Your questions may be discussed in lecture, but if not, ask on Piazza! By doing these simple steps before class, you will be able to understand the material covered in class much better and will have to spend less time after class trying to catch up!

Know that it is okay to ask questions when you don’t understand. There is no such thing as a stupid question. Acknowledging that you don’t understand is the first step you need to take in order for you to be able to understand. You can seek help from:

x Peers - form study groups or use the online discussion boards to ask questions x TA’s - CHEM 233 has a TA in the Chemistry Resource Centre (B357) every day

from 11:30am-2:30pm. They are there to help you understand the materials and concepts

x Instructors - they want you to succeed in their course and would be glad to help you. Go to office hours or schedule appointments to meet with them to go over questions you have.

When you ask for help, make sure you have clear and concise questions, not “I just don’t understand SN2 reactions.” People will be more willing to help if you have thought about the topic and express what you don’t understand rather than asking for a personal lecture. On how to improve your studying: The Carl Wieman Science Education Initiative has a portion of their website devoted to providing resources for science students to improve their studying and learning. Go to the following link and check out the resources: http://www.cwsei.ubc.ca/resources/student_guidance.htm

Pay particular attention to the article and presentation by Robert Bjork, the CWSEI “Succeeding at Learning 101” document (practical advice).

Resources

Assignment For next week’s workshop: Make an example of the following on the topic of an SN1 reaction:

x a good flashcard x concept map x practice problem

We will go over these in groups next week. Please come prepared for the workshop!