Integrated SequencePhysics Chemistry Organic Biology

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Wikipedia - Electrophile
Nice summary of the role of electrophiles in organic chemistry. (At this time, it has been pointed out that there are a few problems with the article, but, overall it is very good).



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Special points of emphasis

Nucleophiles and Electrophiles

Bioenergetics and Cellular Respiration

Integration of Metabolism

The reactions of electrophiles with alkenes constitute one of the four or five most crucial subsets of organic chemistry reactions, both in the course and for the MCAT. You need to go into the MCAT with a comprehensive understanding of these mechanisms. Many MCATs require you to demonstrate you understand the array of considerations governing regio- and stereo- selectivity and specificity in the reactions. The key is to have the mechanisms down cold.

The π bonds between carbon are both weak and electron rich, making them subject to attack by electrophiles. Reactions of electrophiles with alkenes include Catalytic Hydrogenation of Alkenes, Electrophilic Addition of HX to Alkenes, Addition of Sulfuric Acid or Acetic Acid to Alkenes, Acid Catalyzed Hydration of Alkenes, Oxymercuration-demurcuration, Hydroboration of Alkenes, Electrophilic Addition of Halogens to Alkenes, Halohydrin Formation, Allylic Halogenation, Polymerization, Oxidation of Alkenes to Diols, Ozonolysis of Alkenes, and Oxidative Cleavage of Alkenes.




Nucleophiles and Electrophiles

Reactions of Alkynes

Alkynes undergo many of the same reactions with electrophiles as alkenes do such as Catalytic Hydrogenation of Alkynes, Electrophilic Addition of HX to Alkynes, Hydration of Alkynes (followed by rearrangement), Halogenation of Alkynes, Hydroboration of Alkynes



Nucleophiles and Electrophiles

Reactions of Conjugated Species

The reactions of electrophiles with conjugated species have the kinds of twists that MCAT passage writers love. These reactions include 1,2 and 1,4 Addition to Conjugated Diene and Allylic Halogenation.

Always ask yourself if a subject area would lead to an interesting MCAT passage. Although the most important question regarding inclusion on an MCAT is the subject area's importance to the education of future doctors, some topics are better suited for MCAT passages than others, and this naturally leads MCAT writers to them. 1,2 and 1,4 Addition to Conjugated Diene is a case in point. Because of the richness of the issues of thermodynamic versus kinetic control, in addition to standard mechanistic considerations, this reaction finds itself in more than its share of MCATs. As much to do with the test as the importance of the reaction is the fact that the reaction generates wide ranging questions with nice sets of multiple choice answers.




Nucleophiles and Electrophiles

Reactions of Aromatic Compounds

Electrophilic aromatic substitution has been on many an MCAT. You should be able to reproduce the mechanism as well as understand which substituents are ortho-para directing and which are meta directing. The varieties of electrophilic aromatic substitution include Halogenation, Nitration, Sulfonation, Friedel-Crafts Alkylation, and Friedel-Crafts Acylation.



Nucleophiles and Electrophiles

Bioenergetics and Cellular Respiration

Integration of Metabolism

As we have mentioned before, there is a selective pressure for the MCAT writers of the organic chemistry concepts that play the most prominent roles in biochemistry. Biochemical importance is not absolutely determinative. Plenty of MCATs have had core organic chemistry without direct biochemical relevance. Nevertheless, it is an influence. Along this theme, regarding electrophiles, let us mention that biochemically important electrophiles include the hydrogen ion, metal ions, carbonyl carbons, and cationic imines.







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