Module 9

Main Progression - Nucleophiles & Electrophiles, 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 Forms, 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, and Reactions of Organic Sulfur Compounds

Review & Preview - As part of the review for your first practice test in the next module, make a comprehensive review tour of all four disciplines.

Knowledge Mapping - In addition to working to improve your understanding of the physical science basis of organic reaction chemistry, there is a lot of just plain coaching for the test this week in the discussions.

Essay & Verbal Reasoning - Peform ten passages worth of Verbal Reasoning Practice. Continue to analyze your strengths and weaknesses for the different types of questions. Write another essay.

Main Progression

Videos

Assignments

Although conceptual vocabulary with reaction chemistry isn't as central as with some other topics, such as much of the biology, still do go ahead and read the Alkanes Glossary and take a few minutes to perform the Fundamental Terms Crossword Puzzle for reactions of alkanes. This will help orient you to the topic. When you are ready, click here for the Solution to the crossword. Study the WikiPremed Reaction Mechanisms for Alkane Chemistry. Pay special attention to Free Radical Halogenation, an MCAT favorite. Follow the links from the Learning Center to outside Web Resources for Alkane Chemistry beginning HERE. Read pp. 28-32 in Examkrackers Organic Chemistry. Perform the questions on p. 33.

Activate

Goals

	Be able to characterize the geometry, physical properties, and general reactivity of alkanes.
	Know how to reproduce the stoichiometry of the combustion reaction and understand the enthalpy of combustion in terms of bond energy as well as the oxidation-reduction framework.
	Be capable of writing out the mechanism for Free Radical Halogenation of Alkanes.
	Be able to reproduce the explanation of the greater regioselectivity of free radical bromination compared to chlorination in terms of Hammond's postulate.

Activate

Videos

Assignments

Read the Alkenes Glossary and take a few minutes to perform the Fundamental Terms Crossword Puzzle for reactions of Alkenes. When you are ready, click here for the Solution. Study the WikiPremed Reaction Mechanisms for Alkane Chemistry. Although you should become familiar with all of the mechanisms, pay extra attention to Catalytic Hydrogenation, Electrophilic Addition of HX to Alkenes, Free Radical Addition of HX to Alkenes, Acid Catalyzed Hydration of Alkenes, and Electrophilic Addition of Halogens to Alkenes. Follow the links from the Learning Center to outside resources on the web for Alkene Chemistry. Start HERE. Read pp. 34-41 in Examkrackers Organic Chemistry. Perform the questions on pp. 42-43. (This material also covers electrophilic aromatic substitution.)

Activate

Goals

	Be able to characterize the geometry, physical properties, and general reactivity of alkenes. Understand why alkenes are reactive to electrophiles.
	Understand the stereochemical consequences of syn addition in Catalytic Hydrogenation.
	Be able to reproduce the mechanism of the Electrophilic Addition of HX to Alkenes. Understand why the reaction occurs by Markovnikov addition.
	Be able to reproduce the mechanism of the addition of XX (halogen) to alkenes on paper. Understand the stereochemical consequences of the fact that the cyclic halonium intermediate in this reaction leads to anti addition.
	Understand the differences among the various methods for producing an alcohol from an alkene - Acid Catalyzed Hydration, Hydroboration-Oxidation, and Oxymercuration-Demercuration.
	Be familiar with the products of oxidation of alkenes in Oxidation to Diols, Oxidative Cleavage, and Ozonolysis.

Activate

Videos

Videos

Assignments

Read the Alkyl Halides Glossary and take a few minutes to perform the Fundamental Terms Crossword Puzzle. Click here for the Solution to the crossword. Study the WikiPremed Reaction Mechanisms for Alkyl Halides. You need to know SN1 and SN2 Substitution and E1 and E2 Elimination backwards and forwards. Follow the links from the Learning Center to outside resources on the web for Alkyl Halides. Start HERE. Read pp. 44-45 in Examkrackers Organic Chemistry.

Activate

Goals

	Be able to reproduce the mechanisms on paper for SN2 Substitution, SN1 Substitution, E2 Elimination, and E1 Elimination.
	Understand how the substrate, nucleophile, and solvent determine whether SN2 Substitution, E2 elimination, or E1/SN1 will occur.
	Comprehend why a polar protic solvent inhibits the activity of a nucleophile for SN2 substitution, ie. why an aprotic solvent is necessary.
	Be able to articulate the stereochemical consequences of SN2 substitution upon the chiral center of a pure enantiomer as opposed to SN1 substitution.
	Remember that rearrangement may occur with the carbocation intermediate in the E1 or SN1 mechanisms.
	Understand the relevance of Zaitsev's Rule to predicting the position of the double bond resulting from E2 elimination as well as the relevance of the anti periplanar transition state in determining the stereospecificity of the product.

Activate

Videos

Videos

Assignments

Read the Reactions of Aromatic Compounds Glossary and take a few minutes to perform the Fundamental Terms Crossword Puzzle. Click here for the Solution to the crossword. Study the WikiPremed Mechanisms for Reactions with Aromatic Compounds. Electrophilic Aromatic Substitution is an MCAT favorite. Follow the links from the Learning Center to outside resources on the web for Reactions with Aromatic Compounds. Start HERE. Read pp. 39-41 in Examkrackers Organic Chemistry.

Activate

Goals

	Make sure you can construct the generic mechanism for Electrophilic Aromatic Substitution on a blank sheet of paper.
	For Electrophilic Aromatic Substitution occuring upon a ring already containing a substituent, be able to determine whether the substituent is either an Ortho-Para director or a Meta director.
	Be familiar with the specifics of reactions involving the various electrophiles in Electrophilic Aromatic Substitution in Reaction with Halogen, Nitration, Sulfonation, and Friedel-Crafts Alkylation and Acylation.
	Recall the general principles underlying the mechanism of Nucleophilic Aromatic Substitution.
	Recognize the special reactivity of the benzylic position within an alkyl benzene substrate.

Activate

Videos

Assignments

Read the Alcohols and Ethers Glossary and take a few minutes to perform the Fundamental Terms Crossword Puzzle. Click here for the Solution to the crossword. Study the WikiPremed Reaction Mechanisms for Reactions of Alcohols and Ethers. Follow the links from the Learning Center to outside resources on the web for Reactions of Alcohols and Ethers. Start HERE. Read pp. 48-52 in Examkrackers Organic Chemistry. Perform the questions on pp. 53-54.

Activate

Goals

	Be able to picture the means by which acid catalysis activates the hydroxyl group as a leaving group, enabling alcohols to undergo SN1 Substitution or E1 Elimination.
	Remember that Thionyl Chloride and Phosphorus Tribromide enable the transformation of an alcohol into an alkyl halide.
	Be able to assign oxidation number to the hydroxyl carbon of an alcohol and be able to place alcohols within the redox sequence including aldehydes/ketones and carboxylic acids.
	Understand the acid-base properties of alcohols and the significance within reaction chemistry, i.e. the use of alkoxide anion as a nucleophile.
	Recall how ethers may be formed as well as characterize their reactivity.
	Be capable of elucidating the nature of epoxides, their formation and basic reactivity.

Activate

Videos

Assignments

Read the Aldehydes and Ketones Glossary and take a few minutes to perform the Fundamental Terms Crossword Puzzle. Click here for the Solution to the crossword. Study the WikiPremed Reaction Mechanisms for Aldehydes and Ketones. Because of the importance of aldehydes and ketones in biochemistry, these mechanisms seem to have a special focus on the MCAT, especially Acetal Formation and Aldol Condensation. Follow the links from the Learning Center to outside resources on the web for Alkyl Halides. Start HERE. Read pp. 55-61 in Examkrackers Organic Chemistry. Perform the questions on pp. 62-63.

Activate

Goals

	Be capable of characterizing the two major classes of aldehyde-ketone reactions, those involving nucleophilic attack on the carbonyl carbon and those occuring by means of keto-enol tautomerism.
	Although you don't need to worry about every proton movement, you should be able to reproduce the decisive phases of Acetal Formation, Reductive Amination, and Reaction of Aldehydes and Ketones with Grignard Reagents.
	Be able to recognize and characterize these other reactions involving nucleophilic attack on a carbonyl carbon if they are presented to you: The Wittig Reaction, The Wolff-Kishner Reaction and The Cannizzaro Reaction.
	Recognize an enol. Be comfortable reproducing acid or base catalyzing enolization on paper.
	Understand what it means to say that Aldol Condensation involves both keto-enol tautomerism and nucleophilic attack on the carbonyl carbon. Know this reaction backwards and forwards.
	Be able to predict the product from the reagents for Alpha Halogenation, Haloform Reaction, as well as Conjugate Nucleophilic Addition. Have a good sense of these mechanisms.
	Understand the place of aldehydes and ketones in the redox sequence with alcohols and carboxylic acids.

Activate

Videos

Assignments

Read the Carboxylic Acids and Derivatives Glossary and take a few minutes to perform the Fundamental Terms Crossword Puzzle. Click here for the Solution to the crossword. Study the WikiPremed Reaction Mechanisms for Carboxylic Acids and Derivatives. There are many examples within these reactions of the acyl substitution mechanism, which you must have down pat. Follow the links from the Learning Center to outside resources on the web for Carboxylic Acids and Derivatives. Start HERE. Read pp. 64-67 in Examkrackers Organic Chemistry. Perform the questions on p. 68.

Activate

Goals

	Understand how resonance stabilization of the carboxylate anion promotes the acidity of carboxylic acids.
	Understand the order of stability among carboxylic acid derivatives.
	See nucleophilic acyl substitution mechanisms as recapitulations of a general mechanism involving formation and resolution of a tetrahedral intermediate: Acid Halide Formation, Fischer Esterification, Use of Carboxylate Anion Nucleophile to form Esters, Hydrolysis of Acid Halides, Reaction of Acyl Halide with Ammonia or Amine, Esterification of Acid Halides, Esterification of Acid Anhydrides, Saponification of Esters. Acyl substitution appears on many MCATs.
	Understand the role acid catalysis plays in facilitating some acyl substitution mechanisms.
	Be able to recognize and follow Claisen Condensation, Nitrile Hydrolysis, Nitrile Reduction or Hofmann Rearrangement if you were presented with the mechanism.

Activate

Assignments

Read the Reactions of Amines Glossary and take a few minutes to perform the Fundamental Terms Crossword Puzzle. Click here for the Solution to the crossword. Although amine reactions aren't separated out within the WikiPremed Organic Mechanisms, they may often appear as nucleophiles within other categories. Follow the links from the Learning Center to outside resources on the web for Amines. Start HERE. Read pp. 69-76 in Examkrackers Organic Chemistry. Perform the questions on pp. 77-78

Activate

Goals

	Understand the properties of amines as weak bases.
	Be familiar with Amine mechanisms we have seen in other contexts including SN1 or SN2 Substitution with Alkyl Halides where an Amine is the nucleophile, the reaction of Amines as the nucleophile with Aldehydes and Ketones such as occurs in Reductive Amination, the the reaction of Amines with Carboxylic Acid Derivatives such as with Acyl Halides and in Hofmann Elimination.

Activate

 

Review & Preview

Assignments

Practice recreating the WikiPremed outlines of Physics, Chemistry, Organic Chemistry, and Biology with a blank sheet of paper until you can reproduce all four from memory. Use ManDala to carry out a substantial review cycle. Make sure you know the basic terminology from beginning to end. Play at at Level 2, without rolling movement dice but still rolling difficulty dice, moving one space at a time, and see if you can make it from Physics all the way to Biology. Carefully look over the figures in each chapter and try to imagine the kinds of phenomena you might see in MCAT passages. Go one topic at a time and do not proceed to the next topic until you have answered three questions in a row. Skip Photosynthesis, Animals, and Plants if you like. Use your question book and slider for this exercise instead of the online question server so that you can browse each chapter's figures as you go. You are cramming for the MCAT which is the day after tomorrow! You forgot to study! Read quickly through the conceptual discussions in Examkrackers Physics, General Chemistry, Biology from beginning to end. (You will have read most of the Organic Chemistry this week as part of your review of the Mechanisms in the Main Progression) I know it feels impossible. Try to get through it in five or six hours. Imagine the test is the day after tomorrow! What would you do?

Activate

Goals

Since the beginning of the course in our Main Progression we have been tunneling through the mountain. In Review & Preview we have been surveying the mountain. After this week, you should be able to see the disciplines in great detail from the bird's eye view. Now to the end of the course you will know what you need to know. You need to begin to think of your knowledge base as a performance that you refine in testing. Begin holding yourself responsible for the comprehensive MCAT material at the level of fundamental principles from beginning to end.

Be able to clearly picture the phenomena described within each main topic of of the four scientific disciplines and describe at least one or two main concepts from each topic.

Activate

 

Knowledge Mapping

 

Verbal Reasoning

Assignments

Revisit the WikiPremed treatment of Verbal Reasoning on the MCAT. Perform Passages 11-20 in Examkrackers MCAT101 Passages in MCAT Verbal Reasoning. Go through the test you completed. Label every question by type in the margin: Main Idea, Author's Tone, Thematic Extension, Specific Inference, or Facts & Information. Which types seem to be giving the most problems? In the ones you missed, how do your chosen answers differ from the correct answers?

Activate

Goals

	Remember the five main types of Verbal Reasoning questions. Main Idea Author's Tone Thematic Extension Specific Inference Facts & Information
Verbal Reasoning Tip of the Week If you think an answer must be wrong because it seems too easy, don't argue yourself out of it. Some of the questions are easy. Trust yourself.

Activate

 

Essay

MECHANICS AND WAVES		Course Modules
	Kinematics Newton's Laws Work, Energy, and Power Momentum and Impulse
* * *	Rotation Harmonic Motion Elastic Properties of Solids Fluid Mechanics Waves
FUNDAMENTAL FORCES
	Gravitation Electricity
THE STRUCTURE OF MATTER
	Atomic Theory Periodic Properties The Chemical Bond Intermolecular Forces
	Functional Groups in Organic Chemistry Stereochemistry
THERMODYNAMICS AND KINETICS
	Temperature and Heat Flow The Ideal Gas and Kinetic Theory The First Law of Thermodynamics Stoichiometry Thermochemistry
	The Second Law of Thermodynamics and Heat Engines Chemical Thermodynamics and the Equilibrium State The States of Matter The Physical Properties of Organic Compounds Chemical Kinetics
SOLUTIONS AND AQUEOUS SYSTEMS
	Water Solutions Acids and Bases Organic Acids and Bases
ORGANIC REACTION CHEMISTRY
	Nucleophiles and Electrophiles 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
break
BIOMOLECULES
	Proteins Carbohydrates Nucleic Acids Lipids
THE CELL
	Biological Membranes The Prokaryotic Cell The Eukaryotic Cell
BIOENERGETICS AND BIOSYNTHESIS
	Coordination Chemistry Oxidation/Reduction Oxidation/Reduction in Organic Chemistry Electrochemistry Bioenergetics and Cellular Respiration Photosynthesis  optional for MCAT Integration of Metabolism
GENETICS & REPRODUCTION
	Gene Expression Cellular Reproduction Mendelian Genetics Recombination and Mutation The Molecular Biology Laboratory Human Genetics
DIVERSITY OF LIFE
	Viruses Monera Protista  taxonomy optional for MCAT Fungi Plants  optional for MCAT Animals  taxonomy optional for MCAT Animal Development and Embryology
	Mammalian Tissues and Histology
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
	Evolution Ecology
ELECTROMAGNETISM, LIGHT, AND MODERN PHYSICS
	Electricity DC Current Magnetism Electomagnetic Induction AC Current
	The Properties of Light Geometric Optics Wave Optics
	Modern Physics  relativity optional for MCAT Molecular Spectroscopy
	Molecular Spectroscopy Nuclear Physics
break