Organic Chemistry content on the MCAT

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Novis619

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I'm a transfer student at UCSD and I'm currently in my second quarter. Ochem is split into three lectures: 140A, 140B, 140C, and lab 143A. I'm currently enrolled in 140A and I'll be taking 140B in the spring. I am debating whether or not to take 140C in the summer before my August MCAT. I am taking TPRH course from June 18 to August 13 and Summer Session I is from July 4 to August 3. Would it be wise to take the summer course along with my prep course? Or should I just take the class in the fall? Lastly, is Ochem lab critical for the MCAT?

This is the course description of 140C: Organic chemistry of biologically important molecules: carboxylic acids, carbohydrates, proteins, fatty acids, biopolymers, natural products.

140A: Introduction to organic chemistry, with applications to biochemistry. Bonding theory, isomerism, stereochemistry, chemical and physical properties. Introduction to substitution, addition, and elimination reaction, respectively.

140B: Methods of analysis, chemistry of hydrocarbons, chemistry of the carbonyl group. Introduction to the reactions of biologically important molecules.

Thanks in advance.

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What a strange way for your school to do things. It sounds like you're not on a trimester system, so I wonder why they split it up like that.

I think you need to go ask the premed advising office of your school whether or not just taking the two is adequate to prepare you for the MCAT. The reason I say that is that several of the subjects in the C course appear to be commonly tested on the mcat (especially carbohydrates).

The other question is also how much you think you'll be able to get out of the orgo part of the TPR course, and if that would be enough to make up for your classroom deficiency in that area. TPR does a solid job teaching that stuff; you would need to be very diligent about understanding it and going to office hours when you don't, though.
 
I'm a transfer student at UCSD and I'm currently in my second quarter. Ochem is split into three lectures: 140A, 140B, 140C, and lab 143A. I'm currently enrolled in 140A and I'll be taking 140B in the spring. I am debating whether or not to take 140C in the summer before my August MCAT. I am taking TPRH course from June 18 to August 13 and Summer Session I is from July 4 to August 3. Would it be wise to take the summer course along with my prep course? Or should I just take the class in the fall? Lastly, is Ochem lab critical for the MCAT?

This is the course description of 140C: Organic chemistry of biologically important molecules: carboxylic acids, carbohydrates, proteins, fatty acids, biopolymers, natural products.

140A: Introduction to organic chemistry, with applications to biochemistry. Bonding theory, isomerism, stereochemistry, chemical and physical properties. Introduction to substitution, addition, and elimination reaction, respectively.

140B: Methods of analysis, chemistry of hydrocarbons, chemistry of the carbonyl group. Introduction to the reactions of biologically important molecules.

Thanks in advance.

Ah a fellow Triton 🙂

I took all 3. 140A and 140C together pretty much as you covered.
Everything in 140A is on the MCAT Ochem topic list and is indeed on the AAMC practice tests and in review books, and 140C is also very helpful because it's the course that links Ochem with biochemistry. 140B isn't quite as relevant because it's a lot of emphasis on IR and NMR, which the MCAT tests on only marginally. You only need to know a few basic methods of discerning structures (mostly NMR) and you'll be good for the MCAT.

I felt that of all 3 courses, Ochem 140C was THE most helpful one for me in terms of the MCAT. This is because the MCAT likes to test biologically relevant ochem...amino acids, carboxylic acids, esters, amines and amides, fatty acids, etc. 140C is very relevant to the MCAT. Also, it's quite straightforward (unlike 140B which I didn't find very good).

If you can handle the work, I recommend taking it alongside prep if that's the ONLY other summer couse you have since summer classes are 3 hours long. Only do this if you think you can handle an extra 2 lectures a week, 3 hours each (I think that's how long they are). Also, how good is your basic bio, physiology, and genetics? The bio section is mostly non-ochem, so if you are lacking in the biological sciences, then it might be more worth your time to stick with your course's ochem so that you have more time to review the actual bio. It comes down to 1. how well you know actual bio, and 2. how much you can handle in terms of course load, since you'll be taking TPR and a full ochem course.

Do you know who is teaching 140C yet? I had Kim Albizati, and he was possibly the best professor I ever had during my 4 years at UCSD. If you have a good professor and you keep up in your ochem class, you can probably afford to just skim the Ochem content in your prep course because you'll be very well prepared. I took 140C almost 2 years ago now and it has stuck with me...I rarely miss more than 1 or 2 Ochem questions on the AAMC thanks to Albizati..

Finally, for Ochem Lab...Yes, it does help, and UCSD's ochem lab is actually pretty good in covering pretty much all the things you'll need to know about lab techniques on the MCAT, but that's because it's mostly basic lab techniques. Since you go to UCSD, ask around for a UCSD Ochem lab manual (its cheap used) - it's pretty good and it covers pretty much everything on the MCAT topic list for lab techniques. You don't need to read the whole thing or take the course, but it might be worth picking up just to have as a more in depth reference for when you're studying with your MCAT course. Should run for under $20.
 
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I didn't read the above post as I'm quite busy, but in reading your question, I can try give some pointers regarding the o-chem section. I apologize in advance for the length, but I'd like to address all your points as best I can. Firstly, on my exam, the o-chem was quite basic and comprised very little of the section. There was some basic nomenclature, but not a ridiculous amount. There was one question that I'm sure tricked a lot of people. It was a bromination question and at first glance, I almost missed that two of the alkenes in question were different pre-reaction but actually yielded one product in common after bromination. I'd take a look at those kinds of situations (there's also a very simple variation on the SN2 reaction called SN2' that may be worth a quick glance). Simply put, it occurs when you have an allylic halide that gets attacked at the carbon farthest from the halide such that the double bond moves and displaces the halogen. As a simple example:

CH2=CH-CH2-Br + Nu- ---> Nu-CH2-CH=CH2 + Br-

If you can't make sense of that, review your substitution reactions. And as always, recognize that elimination is almost always in competition with substitution and is favored by heating the mixture.

For your other questions, knowing stereochemistry is absolutely a must. I had a question that just gave the name of the reactant and its configuration, told you what it was treated with, and had you pick the name of the product. It was kind of tricky because it was clear it was an SN2 reaction, so instinctively I almost chose the answer that simply had inverted stereochemistry, but remember, inversion of stereochemistry doesn't necessarily mean inversion of absolute configuration (R-> S or S-> R). It depends on the nucleophile and the nature of the other substituents! Take the extra time to draw the reactant and product and actually assign configurations based on the CIP rules. In my case, it was S and stayed S, despite being SN2.

I don't recall too much about fatty acids, but it's good to understand their amphiphilicity and how it can be exploited in various ways (all that comes to mind is acid/base extraction, but the solvents would have to be chosen carefully). DEFINITELY know carbonyl chemistry. There will almost certainly be a question whose sole purpose is to test your understanding of leaving groups and know when carboxylic acid derivatives can be converted (i.e. acyl halide to ester). Also remember that when you throw a carbonyl compound into acid, the carbonyl oxygen generally gets protonated before anything else, and it's this formal positive charge that makes the carbonyl carbon more electrophilic to the conjugate base of whatever acid was used.

Carbohydrate chemistry was basic. Know how to assign configuration based on Fisher projections and whether a ring carbohydrate is alpha or beta. Proteins you don't need to know too much except their general structure. Don't worry about the structures of each amino acid (but it might be wise to recognize that glycine is the only achiral AA). They may give you a peptide chain and ask how many distinct AA's are present, which just requires that you know the general NH2-CHR-COOH structure and be able to see the subunits. This is analogous to being given a polymer and determining the subunit that made it or, alternatively, being given a subunit and being asked what polymer it would create (review radical polymerization).

Know general bonding theory (hybridization) and what geometries different molecules adopt (remember, electronic and molecular geometries are not always the same!). Isomerism is pretty straightforward. I don't think they'd throw a carbocation rearrangement question at you, but you'd do well to be able to spot them. Reactions of hydrocarbons is important but may or may not be tested. Just be familiar with alkene, alkyne, and alkane reactions, including combustion reactions (contrary to popular belief, CO2 and H2O are not the only products of combustion and water sometimes isn't a product at all. Remember all you're introducing is O2, so the products can only contain elements present in the combusted material. I had a question about this in which hydrogen was absent, hence H2O not being a product).

Finally, I think o-chem lab could be beneficial, but understanding the techniques is far more beneficial. For example, if you're given a mixture of 3 components (structures given) and are told the protocol used to separate them, would you be able to logically deduce which compound is removed at which step and why? It generally amounts to hydrophobicity/hydrophilicity or acid/base extraction. Recrystallization may also appear, but generally just looking at a PC table is sufficient. The key idea is that you want a solvent that solvates the solute to significantly different extents with changing temperatures. Something soluble in both cold and hot water, for example, will not recrystallize. Another lab concept that may be tested is boiling points, but again, these will likely be given in a PC table. Questions to ask yourself, should/can I use simple distillation to separate these? Do the substances decompose at a certain temperature? etc.

I think I covered most of your points the best I could, but feel free to ask any further questions. If you're taking an actual prep course, I wouldn't burden yourself with o-chem as well unless you really don't feel comfortable with it. I took 21 credits the semester I took the MCAT and only had spring break to study. I pulled it off, but it was stressful. If you can avoid unnecessary pressure, do it. Hope this helps some, and good luck!
 
Oh, I didn't address spec id. I don't know about other exams, but mine did have a couple questions that required basic knowledge of instrumental analysis. You won't need anything beyond IR and NMR, though they may throw in some MS data to overwhelm you. Just remember, if it's not an exact-mass MS, it's not all that useful. Sure, you can find some fragments that may complement your findings from the other spec data, but if you study mass spec, you'll see that sooo many fragmentation patterns are possible and it can get tedious. Might be worthwhile to understand the M and M+1 peak (M is generally most prominent unless the compound is an alcohol, in which case M-18 is the most prominent; M+1 just represents those compounds containing carbon-13 and is a tiny peak. Bromine and chlorine also give distinctive fragments based on their natural abundance. Two peaks of equal intensities and two units apart indicates presence of bromine; two peaks with intensities of 1:3 and two units apart are indicative of chlorine). A systematic approach would be to look for -OH stretches, SP or SP2 C-H stretches, and C=O or C=C stretches in the IR. Then look for aldehyde or carboxylic acid peaks in the NMR (downfield of 10 ppm) aromatic hydrogens (7-8 ppm), and finally, in the alkyl region, look at multiplicities to determine the correct structure. I also have a feeling they might give you a compound and ask how many peaks you'd expect to see in a 1H-NMR or 13C-NMR spectrum, which tests your understanding of chirality/chemical equivalency. Remember, diastereotopic hydrogens will show up as separate peaks but enantiotopic hydrogens will not. I know my school now covers DEPT-90 and DEPT-135 experiments even in undergraduate o-chem, but this may be beyond the scope of the MCAT. A friend of mine recently took the exam and I think he had a passage on LC or GC, I can't remember. The needed information was given in the passage, but it wouldn't hurt to review it and would save you time if you encounter such a question.
 
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