Orgo I Advice

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Bacteria Boy

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Hi everyone! I'm in need of some advice.

I took my first Orgo test of the semester and found out that I scored a 54! Never have I received a score so low on an exam. I want to get an A in this class, and so immediately freaked out, and by my calculations, the only way that is possible is if I get a 100 on every single quiz and test remaining in the semester and score an A on the final. I took Gen Chem II last semester and got a 100, but Orgo is giving me a headache (the sight of a chair conformation literally causes me physical pain).

tl;dr: what specific resources (aside from an SI session because I don't absorb information as quickly with that type of thing) did you all use to get an A in this class? KhanAcademy, study guides from Amazon, etc.?

Thanks in advance.
 
Organic Chemistry as Second Language by David Klein is pretty good and popular among members here.

I second this, it was a really good resource for high yield concepts when I took Orgo.
 
Buy a model kit. Seeing it in 3D will help you learn to translate the 2D drawings.
 
Organic Chemistry as Second Language by David Klein is pretty good and popular among members here.
This helped a lot of people in our class. What textbook do you use? I use Klein's textbook and the answer guide and it has been wonderful. The end of chapter questions start easy and work up to harder questions than our exams. Our lectures are pretty useless so I've used that textbook almost exclusively to teach myself (I'm in orgo 2 now)
 
A whiteboard. Seriously. You MUST draw out organic chemistry to understand it. The second part of Organic I at my school was just a TON of reactions. They are not hard, there is just a lot of them. Practice, practice, practice. It takes time to get it all down. Mechanisms will you help you understand why and how reactions work, but they take time. Recognizing what you can do with functional groups is essential. Currently, I'm in organic II, so hopefully what follows helps a bit. I'm not trying to impress you with my knowledge, I'm just trying to get you to understand the thought process.

One exercise that is very useful is to start off by thinking of a molecule, with a whiteboard in front of you. Usually I just start drawing carbon chains or rings and then add a function group, and then pick a product I want to achieve that has an attainable functional group. Take for instance benzoic acid, let's make that our product. How can we make benzoic acid using anything we need? Let's start close to home with benzaldehyde. We need to take this aldehyde to a carboxylic acid. What process does benzaldehyde need to undergo to gain an oxygen/alcohol? What converts an aldehyde to a carboxylic acid? A strong oxidizing agent should do the trick. Potassium permanganate in water will take you to benzoic acid.

Now, exercise a different way you could get to benzoic acid. This time, start with just benzene. Friedel-crafts acylation with formyl chloride in aluminum chloride can take you to benzaldehyde, and now you can just use the oxidizing step you used before. You could have also use Friedel-crafts alkylation with methyl bromide in aluminum chloride to get toluene, and then use a strong oxidizing agent again. Benzoic acid results. These two methods are similar, but you just used your knowledge of A.) nomenclature (structure from name), B.) Aromatic reactions (F-C Alk, acyl), and C.) Oxidation.

If you can, try to always name your reagents and products. My instructor always put stuff in words on the exam so it could get pretty scary if you could only recognize structures but not names. This tripped up quite a few people in my class. Now, back to the reaction.

What's another way I can get benzoic acid? Well, let's say I had only carbon dioxide as my initial source of carbon. I know I'm going to need to add that benzene ring somehow. I recognize that there is two oxygens in CO2, and my product also has 2 oxygens. CO2 also has one carbon, so I need to add 6 carbons to get to my product. How can I do it? Well, with the grignard reaction I can add phenylmagnesium bromide in ether to get me to benzylate ion, which I can then give an acid to bring me to benzoic acid. Try to understand what exactly is happening in the grignard reaction. It's a carbanion attacking a carbonyl. Practice moving the carbanion electrons to the carbonyl, and then pushing the bonding electrons (otherwise our octet would be broken) up to the oxygen to give us the ion. Practice moving the electrons from the benzylate ion's oxygen to go grab the extra proton off the acid.

This is how I think when I practice reactions. Retrosynthetic analysis, as my professor calls it, requires you to know everything about the reaction. There are many pathways in organic that can achieve the same result (on paper). When you repeatedly practice these pathways, synthesis problems on an exam will be easy because you have so many different ways you can utilize functional groups. I did something like 12 steps for a 3 step problem on my second organic exam and got full credit (and a 100 overall). Now obviously if a question says use 3 steps, you use 3 steps. But, you have to build this toolbox that allows you to have as many options as possible so you have access to those exact 3 steps.

Hope this helps, and my apologies if you haven't covered the reactions I mentioned. This was the material that was covered around this time in the semester for my organic I.
 
I used Khan academy, and I focused a large portion of my time on mechanisms. For Ochem I, it's important to know the reagents, and have a solid understanding of what they do. That way if your professor gives you a mechanism problem with 8 reagents, you will have a handle on what your product should be. Also, go to your professor's office hours and see if you can rework those problems. That way you can highlight any areas that might be difficult, and the professor can offer you tips on how to get a better grasp of the material.
 
A whiteboard. Seriously. You MUST draw out organic chemistry to understand it. The second part of Organic I at my school was just a TON of reactions. They are not hard, there is just a lot of them. Practice, practice, practice. It takes time to get it all down. Mechanisms will you help you understand why and how reactions work, but they take time. Recognizing what you can do with functional groups is essential. Currently, I'm in organic II, so hopefully what follows helps a bit. I'm not trying to impress you with my knowledge, I'm just trying to get you to understand the thought process.

One exercise that is very useful is to start off by thinking of a molecule, with a whiteboard in front of you. Usually I just start drawing carbon chains or rings and then add a function group, and then pick a product I want to achieve that has an attainable functional group. Take for instance benzoic acid, let's make that our product. How can we make benzoic acid using anything we need? Let's start close to home with benzaldehyde. We need to take this aldehyde to a carboxylic acid. What process does benzaldehyde need to undergo to gain an oxygen/alcohol? What converts an aldehyde to a carboxylic acid? A strong oxidizing agent should do the trick. Potassium permanganate in water will take you to benzoic acid.

Now, exercise a different way you could get to benzoic acid. This time, start with just benzene. Friedel-crafts acylation with formyl chloride in aluminum chloride can take you to benzaldehyde, and now you can just use the oxidizing step you used before. You could have also use Friedel-crafts alkylation with methyl bromide in aluminum chloride to get toluene, and then use a strong oxidizing agent again. Benzoic acid results. These two methods are similar, but you just used your knowledge of A.) nomenclature (structure from name), B.) Aromatic reactions (F-C Alk, acyl), and C.) Oxidation.

If you can, try to always name your reagents and products. My instructor always put stuff in words on the exam so it could get pretty scary if you could only recognize structures but not names. This tripped up quite a few people in my class. Now, back to the reaction.

What's another way I can get benzoic acid? Well, let's say I had only carbon dioxide as my initial source of carbon. I know I'm going to need to add that benzene ring somehow. I recognize that there is two oxygens in CO2, and my product also has 2 oxygens. CO2 also has one carbon, so I need to add 6 carbons to get to my product. How can I do it? Well, with the grignard reaction I can add phenylmagnesium bromide in ether to get me to benzylate ion, which I can then give an acid to bring me to benzoic acid. Try to understand what exactly is happening in the grignard reaction. It's a carbanion attacking a carbonyl. Practice moving the carbanion electrons to the carbonyl, and then pushing the bonding electrons (otherwise our octet would be broken) up to the oxygen to give us the ion. Practice moving the electrons from the benzylate ion's oxygen to go grab the extra proton off the acid.

This is how I think when I practice reactions. Retrosynthetic analysis, as my professor calls it, requires you to know everything about the reaction. There are many pathways in organic that can achieve the same result (on paper). When you repeatedly practice these pathways, synthesis problems on an exam will be easy because you have so many different ways you can utilize functional groups. I did something like 12 steps for a 3 step problem on my second organic exam and got full credit (and a 100 overall). Now obviously if a question says use 3 steps, you use 3 steps. But, you have to build this toolbox that allows you to have as many options as possible so you have access to those exact 3 steps.

Hope this helps, and my apologies if you haven't covered the reactions I mentioned. This was the material that was covered around this time in the semester for my organic I.
Tl;Dr Synthesis Roadmaps :laugh:
 
Don't study to memorize. If you understand the concepts 95% of orgo can be worked out through Logic and understanding of the concepts and theory behind reactions/mechanisms/etc..
 
^I don't think I have the brain capacity to memorize all of the material covered in Orgo I alone.

Thanks to everyone who responded. I'm on spring break this week and have been using some of my free time to read Organic Chemistry As a Second Language and watch Khan Academy videos. I will also look into getting a model kit, because in addition to helping me understand reactions, they're pretty cool.

Also, thank you Hospitalized for your exceedingly thoughtful and thorough post. You have certainly been helpful.

I am a chemistry major... So hopefully this stuff starts sinking in!
 
I know this isn't directly answering your question, but not getting an A in orgo is not the end of the world. I know some people who didn't even get a B+ and ended up in a top med school(US news ranked top 15).

As far as studying goes, it helps to study with somebody and take turns explaining concepts to each other.
 
^I don't think I have the brain capacity to memorize all of the material covered in Orgo I alone.

Thanks to everyone who responded. I'm on spring break this week and have been using some of my free time to read Organic Chemistry As a Second Language and watch Khan Academy videos. I will also look into getting a model kit, because in addition to helping me understand reactions, they're pretty cool.

Also, thank you Hospitalized for your exceedingly thoughtful and thorough post. You have certainly been helpful.

I am a chemistry major... So hopefully this stuff starts sinking in!

The best advice I can give is to understand how each molecule, functional group, atom reacts, etc. Memorize electronegativity trends, where electrons tend to flow in reactions, look at mechanisms to understand how reactions work, and most of all practice! I understood the basics from each chapter, and then did every single problem in my orgo book to practice so that I could learn trends and specifics of reactions. This made orgo I and orgo II easy! You can just take what you know and logically figure out what step will happen next in the reaction. Also, if you really get interested in the topic, it makes it much more enjoyable 🙂
 
I think that how you study is much much more important than what materials you study. Personally, I just used my class's textbook (Wade). To actually study, I go through the textbook along with my lecture notes as I guide, and I make a list of all of the reactions in a given chapter. Then, on plain white paper, I very neatly draw out the mechanisms with the aid of my textbook, and add any brief relevant notes (i.e. regioselectivity, when/where this reaction can/cannot be used, etc). (These also make great study guides for the final!) After I've done this, I go through the list of reactions and "quiz" myself. If it's a complicated mechanism with arrow pushing, I make sure that I can draw it out completely without looking at my notes, multiple times. While I do this, I don't just memorize where the arrows go, or a list of reagents, I try to understand why each step of the reaction happens. Ex: What makes this a good nucleophile? What makes this hydrogen more acidic than that hydrogen? Etc. At this point, I should have a good understanding of all of the reactions (not just memorization). Personally, I think it's important to have the reactions squared away in your head, so that when you do practice problems, you don't rely on your notes (I find it works best to completely deprive myself of my notes while doing problems, except for when checking my answers). If you are still confused about anything, you should now what specifically what you're confused about, and you can go to office hours, ask a friend, or use online resources to really figure out that concept Finally, practice practice practice. Do every problem in your book. Go to the library and check out an older orgo textbook. Do those problems if you feel like you need more. The more you do, the more you will begin to recognize patterns, figure out things that easily trick you in a problem, etc.

As others have mentioned, having a model kit is super helpful. Some reactions make no sense on paper, but when you look at the molecule in 3D, it can just "click". The kits are great for visualizing dihedral angles. Also, they make it 100% easier to visualize reactions involving cyclohexane and its derivatives.

Also, the importance of thinking about problems retrosynthetically cannot be stressed enough. My professor used to always tell us to "think retrosynthetically" and I never really understood what he meant until late in the semester when we did more synthesis problems. But I think that the earlier you can learn to use retrosynthesis, the better. So, don't just think about the forward reaction. When you are studying, even if the question just asks for something in the forward sense, look at every product and think, how can I make that using the reactions that I've learned? Often there are multiple ways. As you learn more reactions, synthesis problems will become more helpful.

Finally, a good trick for any class is to try to explain things to other people, even if it's just to a stuffed animal. This can really help you figure out what you actually know and what you have trouble on.

Overall, I think the most effective thing I've done to study is to make the lists of reactions for each chapter. Knowing explicitly what reactions I need to know, which ones I am comfortable with, and which ones I am confused about really helped!
 
Buy a model kit. Seeing it in 3D will help you learn to translate the 2D drawings.

This helps especially when you are working with cyclohexanes, bicyclic compounds, and diels-alder stereocenters. AKA, those things which are 3-dimensional and difficult to visualize and understand in 2 dimensional drawings.
 
If it's still within your drop period, I would drop. Maybe sit in on the class this semester and retake it next year.
 
I know this isn't directly answering your question, but not getting an A in orgo is not the end of the world. I know some people who didn't even get a B+ and ended up in a top med school(US news ranked top 15).

As far as studying goes, it helps to study with somebody and take turns explaining concepts to each other.

I know, I just have high expectations for myself in Orgo given that I'm actually a chemistry major, and I truly am passionate about chem. When I registered for the course, I personally sent an email to the instructor asking for a class size override, so there's no way that I'm going to earn a bad grade after having done that.

One of my co-workers (who is also pre-med) offered to help me since she is taking Orgo II and says she could use the review as well. I think I'll take her up on the offer.

The best advice I can give is to understand how each molecule, functional group, atom reacts, etc. Memorize electronegativity trends, where electrons tend to flow in reactions, look at mechanisms to understand how reactions work, and most of all practice! I understood the basics from each chapter, and then did every single problem in my orgo book to practice so that I could learn trends and specifics of reactions. This made orgo I and orgo II easy! You can just take what you know and logically figure out what step will happen next in the reaction. Also, if you really get interested in the topic, it makes it much more enjoyable 🙂

Thanks for the advice. I'm trying to master the basics of all of the chapters thus far and do as many practice problems as possible. I think once I start nailing the practice problems, I'll really start to enjoy the course. 😀

How the hell is that possible??

I second the whiteboard suggestion, starting at pages of mechanisms and synthesis routes <<< drawing them repeatedly

Our teacher curved the ACS final by a crazy amount (like, 15-20 points), so I ended up getting over 100 on it. I had an A before the final, and the final was 20-30% of our grade. The curve was a godsend, I know.

Thanks for the recommendation.

If it's still within your drop period, I would drop. Maybe sit in on the class this semester and retake it next year.

Gah, I don't want to drop it though. I've gone from an F to an A before (Pre-Calc, it was a dark time), so I think I can recover with a bit of applied effort. Thanks for the dose of realism though.
 
I know, I just have high expectations for myself in Orgo given that I'm actually a chemistry major, and I truly am passionate about chem. When I registered for the course, I personally sent an email to the instructor asking for a class size override, so there's no way that I'm going to earn a bad grade after having done that.

One of my co-workers (who is also pre-med) offered to help me since she is taking Orgo II and says she could use the review as well. I think I'll take her up on the offer.



Thanks for the advice. I'm trying to master the basics of all of the chapters thus far and do as many practice problems as possible. I think once I start nailing the practice problems, I'll really start to enjoy the course. 😀



Our teacher curved the ACS final by a crazy amount (like, 15-20 points), so I ended up getting over 100 on it. I had an A before the final, and the final was 20-30% of our grade. The curve was a godsend, I know.

Thanks for the recommendation.



Gah, I don't want to drop it though. I've gone from an F to an A before (Pre-Calc, it was a dark time), so I think I can recover with a bit of applied effort. Thanks for the dose of realism though.

Yah but bruh, orgo isn't precalc. If you're really in a deep hole where you're all but guaranteeing yourself a grade less than an A, I would just swallow my pride because an A in orgo next year beats anything less than an A this year. Just my two cents but I'm sure you'll be fine either way!
 
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