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The MCAT Course Syllabus

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This syllabus will soon be populated with links to a large quantity of free learning materials, a matter of a few days. The present learning tasks do not reflect all the free stuff I have decided to make available, but changing anything to do with this course is a like turning a big ship. It is coming in. I promise you will not be waiting on the dock very long. Stay and read the syllabus, especially the learning goals and try to understand how the Main Cycle, Overview, and Interdisciplinary goals will be working together. I have live students hearing a session on the first module next Monday in Atlanta. Although we will be meeting every other week for ten months, there are students in my live course preparing for the August exam, so you can rest assured things will be ready for anybody starting their MCAT preparation here today.

For the learning tasks, you can see how my works listed on the home page are going to fit in here. I have not made everything you need. You still need a big MCAT book because I decided ten years ago not to create works someone else had already done well enough, so although I have a complete set of physical sciences problem sets, which I composed in 1993 and 1994, I released myself from the burden of writing 500 organic problems. I had other things to do. The Kaplan Book is good, but the ExamKrackers set is better, although it is three times more expensive. You are fine with pretty much any combination of MCAT books that is at least five inches tall on the desk. We will use them for topical problem drill and conceptual cycling and that is about it. The first four modules will soon have links within all the learning tasks to WikiPremed creative commons materials you will be able to download, actually Wednesday barring unforeseen developments.
Main Sequence     Interdisciplinary Discussions     Verbal Reasoning     Essay

Module 5 - Organic Functional Groups, Conformations, and Stereochemistry

We are moving directly to Organic Chemistry from our study last module of Atomic Theory, Periodic Properties, Chemical Bonding, and Intermolecular Forces. In fact, this module will mainly be an Overview Cycle nested within the Main Sequence, a tour of the Organic Chemistry reactions from beginning to end. We will go more slowly through these reactions again later in the course. Many students find reviewing Organic Chemistry for the MCAT to be one of the biggest challenges of preparing for the exam. A consciously structured review process will help your comprehension and retention. With the Organic Chemistry, it is definitely helpful to augment your Main Sequence study with carefully structured Overview Cycles. Triangulation and repetition instead of one slow slog. Look for the patterns underpinning the variety of chemical behaviors across the expanse of material. Instead of twenty five reactions of aldehydes and ketones, for example, look for two big groups with a few sundry tag-alongs.

Module 5 - Overview

Main Sequence - Functional Groups in Organic Chemistry, Conformations of Organic Molecules, and Stereochemistry.

Overview Cycle - There are no specific Epicycle goals or tasks this module. The Main Sequence survey of the Functional Groups is a comprehensive tour of the organic reactions. In other words, the distinction between the two modes of study is not as important this module.

Interdisciplinary Discussions - A great deal of coaching advice on mastering the organic reaction mechanisms and some key discussions in the organic context to prepare us for Chemical Thermodynamics.

Verbal Reasoning and Essay - Review the types of Verbal Reasoning questions and take a Verbal Reasoning practice exam. Analyze your performance. Write an essay.

Module 5 - Main Sequence        { 10 - 12 hours }

This module our Main Sequence topics are Functional Groups in Organic Chemistry, Conformations of Organic Molecules, and Stereochemistry. We will be taking our coverage of the organic functional groups as an opportunity to review the organic mechanisms from beginning to end, the first of many cycles through the reactions in this learning program. The first step in reviewing this large body of material is to re-establish the broad familiarity you possessed at the end of your organic chemistry course. Each subsequent cycle will make your knowledge of the mechanisms richer, more articulated, and more manageable.

Here are our Main Sequence topics for Module 5:















































Functional groups are combinations of atoms within organic molecules that are responsible for the reactivity of the molecules. The functional groups a molecule contains also play a role in determining its physical properties. Although the chemical behavior of a functional group may be modified by overall molecular structure, it is a powerful analytical method to approach the reactivity of an organic molecule in terms of the functional groups it contains.



Functional Groups on the MCAT

Understanding the behaviors of the main organic functional groups in organic chemistry is another way to describe, really, understanding the basics of organic reaction chemistry. Because organic chemistry comprises approximately one third of the Biological Sciences section of the MCAT typically, there will be many instances on the test where you will be called upon to demonstrate familiarity with the properties and behaviors of various organic functional groups.


Learning Goals for Organic Functional Groups


Be prepared to identify all the major functional groups.
Understand the affect of a particular functional group on physical properties and solubility.
Become familiar with the acid-base properties of various functional groups.
Begin consolidating mastery of the organic mechanisms, familiar with the major types of reaction each functional group can undergo, able to easily answer the simpler genre of questions at this stage.

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Suggested Assignments


The main set of tasks this module comprise the several tours you should make of the organic functional groups from beginning to end focusing on their various properties and behaviors in organic reaction chemistry. This is your main focus this module, and you should not hesitate to spend approximately half of your study time with these Main Sequence tasks. The reaction mechanisms are one of your biggest challenges for the exam. Repetition is the key to making the knowledge manageable.

There are several comprehensive treatments of Organic Chemistry on the web, perfectly calibrated for students preparing for the MCAT. Tour the external resources in the Exploration Environment within the chapter on Functional Groups. In the Exploration Environment, start Here. Study the resources within a particular topic. After you have finished within a particular functional group, move on by clicking 'Next Topic'.
Read the Organic Mechanisms Pocketbook from cover to cover.
Continue to another repetition. Saturate your time this module with organic. Get from the beginning to the end of organic at MCAT Pearls. Scope out material. Don't forget that we will be returning again later. Get a few repetitions under your belt.

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The structure of an organic molecule can undergo conformational changes due to free rotation around single bonds. Because of steric hindrance, different forms may possess different internal energy. For example, in the staggered form in ethane, the C-H bonds are rotated far apart, so there is less steric hindrance than occurs in the eclipsed form in which the C-H bonds are parallel to each other. For this reason the staggered from will predominate at equilibrium.


Conformations of Organic Molecules on the MCAT

Questions involving conformational change often appear on the MCAT. Typically, the context will not directly involve ethane or cyclohexane, but more complex situations. Catalysis facilitated by conformational change occuring upon an enzyme substrate undergoing induced fit is a typical example. Also, be aware that students often miss conformation questions by forgetting the partial double bond character which may be imparted to single bonds through resonance, which will prevent free rotation.



Learning Goals for Conformations of Organic Molecules


Understand the factors making the staggered conformation of ethane more stable than the eclipsed conformation.
Be able to recreate the potential energy diagram for internal rotation around the central carbon-carbon bond in butane.
Be capable of differentiating the two staggered conformations of butane, gauche and anti.
Understand the potential energy diagram for the various conformations of cyclohexane: chair, half-chair, skew boat, and boat.
Grasp the conformational analysis of mono- and di-substitution of cyclohexane.

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Suggested Assignments


Read the bold headings, formulas, and captions of the Conformations chapter of a good organic chemistry textbook. This is a topic where the scale of the typical textbook treatment is a good match for the MCAT.
The typical Main Sequence Book tends to short-change this topic, but you definitely want to investigate the treatment within yours to ensure you have a sense of the absolute distillation of this topic.
Review the Conformations of Organic Molecules external resources in the Exploration Environment.
If the conformations problems from your Main Sequence Book seem inadequate, you might supplement your drill with selections from the review questions in your organic textbook.

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Stereochemistry is the branch of chemistry concerned with the spatial arrangements of atoms in molecules. Stereoisomers are molecules which do not differ in the sequential arrangement of atoms, but the spatial arrangment. In our earlier chapter, the Conformations of Organic Molecules, we were concerned with one sub-class of stereoisomerism, conformational isomerism, in which interconversion between the differing forms may occur without breaking bonds. In contrast, however, configurational isomers may not be interconverted without breaking bonds. If two configurational isomers are mirror images, they are enantiomers. Configurational isomers which are not mirror images are enantiomers. There is not uniformity of agreement on the definition of enantiomers, however. Some authors include cis - trans isomers as enantiomers, while other others only include forms differing at chiral centers that are not mirror images (having multiple chiral centers).


Stereochemistry on the MCAT

Stereochemistry is a crucial topic for the MCAT. Nearly every exam will contain at least one question dealing directly with stereochemistry and several questions dealing indirectly. An MCAT passage presenting a reaction mechanism will often be followed by at least one question dealing with issues such as inversion of configuration or racemization. Students are often asked to recognize meso- forms on the MCAT or predict the number of stereoisomers a structure may have. Watch for stereochemistry to be presented on the MCAT in an unusual context such as coordination chemistry.



Learning Goals for Stereochemistry


Check off your learning goals when completed.
I understand the distinctions between the various kinds of molecular isomerism. I can reproduce an organizational map beginning with geometric isomerism vs. stereoisomerism (involving chirality) and proceed to the distinctions within these categories. (Be prepared for subtle disagreements in the literature on some of these definitions.)
Be able to correctly predict whether two stereoisomers are enantiomers or diastereomers.
Be aware of what it means for a molecule to be a meso form.
Understand the different systems of stereochemical nomenclature. You only need to be familiar with carbohydrate nomenclature, where the MCAT won't expect a great deal.
Learn how to solve problems with molecules having multiple chiral centers such as predicting the number of stereoisomers and recognizing which are enantiomers.
Grasp the role of stereoisomerism in the chemistry lab. Be able to predict which reactions produce racemic mixtures, for example, and be able to discuss laboratory techniques involving resolution of enantiomers.

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Suggested Assignments


Read the bold headings, formulas, and captions of the Stereochemistry chapter of a good organic chemistry textbook. As with Conformations, this is a topic where the scale of the typical textbook treatment is a good match for the MCAT.
Be sure that you know the Stereochemistry section of your Main Sequence Book backwards and forwards. The material that makes it into an MCAT review distillation will be absolutely essential.
Review the Stereochemistry external resources in the Exploration Environment.
You need to perform a few problems. Your Main Sequence Book should have a problem set on Stereochemistry. You might supplement your drill on this important topic with selections from the review questions in your organic textbook.

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Module 5 - Interdisciplinary Discussions        { 3 hours }

Although there are a few crucial Interdisciplinary Discussions this module under the topic, Conformations of Organic Molecules, staying on the main interdisciplinary road, advancing our understanding of the relationship between the electrostatic basis of chemistry and Chemical Thermodynamics, many of the discussions you will cover before reaching that point, within the topic Organic Functional Groups, are more of the coaching variety.

You will especially notice these two subgenres within the Interdisciplinary Discussions this module, those which are moving the spiraling curriculum forward, and those which are more along the lines coaching, i.e. Tips & Hints, MCAT Advice, and Special Emphasis.

Interdisciplinary Discussion - Learning Goals


Develop a good feel for the personalities of the organic functional groups.
Develop the intuitive, conceptual ability to model conformational analysis for a sample of a pure organic substance, treating the sample as a thermodynamic system.

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Suggested Assignments


Read the Interdisciplinary Discussions for Organic Functional Groups, Conformations of Organic Molecules, and Stereochemistry slowly and carefully. Start HERE to begin the Interdisciplinary Discussions of the Organic Functional Groups, clicking 'Next Discussion' until you reach Conformations. There are about twenty discussions for the Organic Functional Groups and fewer for the other topics.
For this module's concept mapping create one sheet relating Electricity, Conformations of Organic Molecules, Thermochemistry, and Chemical Thermodynamics.

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Module 5 - Verbal Reasoning        { 2 - 3 hours }

It is extremely helpful to approach the Verbal Reasoning exam systematically in terms of the different types of Verbal Reasoning questions. Here is a reprise of the descriptions of the five main types of Verbal Reasoning questions which we introduced in Module 1.

Main Idea
These are general questions dealing with the cardinal issues of the passage. Main idea questions are designed to see if you grasped the central theme of the passage as a whole.

Author's Tone
This type of general question asks whether you understood the author's point of view on the subject of the passage. These questions are often the most subtle. Is the author being critical or supportive. Is their tone objectively neutral or biased and partisan? The differences among the answer choices in tone questions can sometimes be hard to tease out.

Thematic Extension
These questions are in the same family with the Main Idea or Tone questions, which deal with the passage as a whole, but Thematic Extension questions ask you to take the author's argument or point of view and draw a conclusion about another subject or derive a broader proposition.

Specific Inference
These questions will identify a specific section of the passage and ask for an interpretation that goes a little deeper than the explicit reference, asking you to read 'between the lines'. These questions are often about judging the shade of meaning the author puts on a word within a specific context.

Facts & Information
On one level these questions are a test for your retention of specific facts or concepts stated in the passage. However, on another level, they are a test of how well you synthesized and retained the organization and flow of the passage. This is because often the process of answering this kind of question involves returning to the passage to find the information.

Verbal Reasoning Tip of the Week

Both Thematic Extension and Specific Inference questions require you to look beyond the text. With these types of questions, an answer chioce containing wording that is a direct repetition from the passage is usually wrong.

Verbal Reasoning Assignments


Find an undisturbed hour and take a practice Verbal Reasoning test from your Main Sequence Book or your Overview Cycle Book.
Methodically go through the Verbal Reasoning test you completed this week. Label every question by type in the margin: Main Idea, Author's Tone, Thematic Extension, Specific Inference, or Facts & Information. Analyze your performance. Which types of questions seem to be giving you the most problems? Can you spot any trends? In the questions you missed, how do the answers you chose differ from the correct answers?

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Module 5 - Essay        { 1 hour }

This is the fifth essay. The keys to preparing for the essay are to learn a good technique and practice. In module two, we discussed some techniques for structuring a unified critical MCAT essay in some depth. Here is a LINK to that discussion for a refresher.

Essay Assignments


Arrange an undisturbed half hour for yourself to write an essay. You need some plain ruled paper and an erasable pen. Skip lines to give yourself some flexibility for editing as you write. Click Here and the computer will present a PDF file containing your essay topic for module five. Don't advance to page 2 until you are ready to begin writing. If you would like to print out the PDF in order to write your essay away from the computer, be sure not to look at page 2 until you are ready to begin.
After you have written your essay, type it out and post your essay at the FORUM for feedback from your fellow students. If you post an essay for feedback, be sure to give your opinion and advice on at least two essays posted by others.

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MECHANICS AND WAVES
link to syllabus
Kinematics1
Newton's Laws
Work, Energy, and Power
Momentum and Impulse
Rotation2
Harmonic Motion
Elastic Properties of Solids
Fluid Mechanics
Waves
FUNDAMENTAL FORCES
Gravitation3
Electricity
THE STRUCTURE OF MATTER
Atomic Theory4
Periodic Properties
The Chemical Bond
Intermolecular Forces
Functional Groups in Organic Chemistry5
Conformations of Organic Molecules
* * *Stereochemistry
THERMODYNAMICS AND KINETICS IN PHYSICAL AND CHEMICAL SYSTEMS
Temperature and Heat Flow6
The Ideal Gas and Kinetic Theory
The First Law of Thermodynamics
Stoichiometry
Thermochemistry
The Second Law of Thermodynamics and Heat Engines7
Chemical Thermodynamics and the Equilibrium State
The States of Matter
The Physical Properties of Organic Compounds
Chemical Kinetics
SOLUTIONS AND AQUEOUS SYSTEMS
Water8
Solutions
Acids and Bases
Organic Acids and Bases
ORGANIC REACTION CHEMISTRY
Nucleophiles and Electrophiles9
Intramolecular Cationic Rearrangements
Reactions with Radical Intermediates
Conjugated π Systems and Aromaticity
Reactions of Alkanes
Reactions of Alkenes
Reactions of Alkynes
Reactions of Alkyl Halides
Reactions of Allylic and Benzylic Conjugation
Reactions of Aromatic Compounds
Reactions of Alcohols and Ethers
Reactions of Aldehydes and Ketones
Reactions of Carboxylic Acids and Derivatives
Reactions of Amines
Reactions of Organic Phosphorus Compounds
Reactions of Organic Sulfur Compounds
BIOMOLECULES10 break
Proteins11
Carbohydrates
Nucleic Acids
Lipids
THE CELL
Biological Membranes
The Prokaryotic Cell
The Eukaryotic Cell
BIOENERGETICS AND BIOSYNTHESIS
Coordination Chemistry12
Oxidation/Reduction
Oxidation/Reduction in Organic Chemistry
Electrochemistry
Bioenergetics and Cellular Respiration
Photosynthesis  
Biosynthesis of Macromolecules
Integration of Metabolism
GENETICS & REPRODUCTION
Gene Expression13
Cellular Reproduction
Mendelian Genetics
Recombination and Mutation
The Molecular Biology Laboratory
Human Genetics
DIVERSITY OF LIFE
Viruses14
Monera
Protista
Fungi
Plants  
Animals
Animal Development and Embryology
Mammalian Tissues and Histology15
HUMAN PHYSIOLOGY
The Nervous System
Sensory Systems
The Endocrine System
The Musculoskeletal System
The Cardiovascular System
Blood
The Respiratory System
The Lymphatic System and Immunity
The Urinary System
The Digestive System and Nutrition
The Reproductive System
POPULATION BIOLOGY
Populations16
Evolution
Ecology
ELECTROMAGNETISM, LIGHT, AND MODERN PHYSICS
Electricity17
DC Current
Magnetism
Electomagnetic Induction
AC Current
The Properties of Light
Geometric Optics
Wave Optics
Modern Physics18
Molecular Spectroscopy
Nuclear Physics
19 break
20 break

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