Integrated SequencePhysics Chemistry Organic Biology

Web Resources

Virtual Textbook of Organic Chemistry - Main Group Organometallic Compounds
Comprehensive discussion of this very important provider of nucleophilic carbons for organic synthesis (enabling C-C bonding).

Virtual Textbook of Organic Chemistry - Acidity of Terminal Alkynes
The acidity of terminal alkynes provides another source of nucleophilic carbon.

  click if a link is broken

Special points of emphasis

Nucleophiles and Electrophiles

Reactions of Alkynes

Reactions of Aldehydes and Ketones

Reactions of Carboxylic Acids and Derivatives

Reactions of Amines

Reactions that form new carbon-carbon bonds are especially important in organic synthesis. Reagents that can create the possibility for carbon to act as a nucleophile are especially useful in this regard. Sources of nucleophilic carbon include Grignard Reagents, Gilman Reagents (lithium dialkyl cuprates), Acetylide Anions, Enolate Anions, Cyanide Anions and the Phosphorus Ylides of the Wittig Reaction. Nucleophilic carbon enables the formation of new carbon-carbon bonds.

Nucleophiles and Electrophiles


Bioenergetics and Cellular Respiration

Integration of Metabolism

The Digestive System and Nutrition

Here is a little discussion about nucleophilic carbon in a more advanced context, the biochemical context. Read for comprehension. Thiamine pyrophosphate (TPP) is a prosthetic group for three crucial enzymes: pyruvate dehydrogenase (glycolysis), α-ketoglutarate dehydrogenase (citric acid cycle), and transketolase (sugar interconversion mechanisms). TPP serves as a source of nucleophilic carbon for these enzymes. TPP can be easily ionized to present a carbanion for addition to carbonyl groups. This serves to activate the group for further transformations, such as oxidative decarboxylization.

The paragraph above goes a step or two beyond the MCAT level factual basis. It is not meant to say 'Here's what you have to know'. Don't worry that the occasionally dense level of biochemistry in these Interdisciplinary Discussions. It doesn't mean that you must remember a host of biochemical pathways for the MCAT. MCAT passages are fond of biochemistry, but the test-writers want to see if you have the basis in the fundamentals to hang on to the discussion. For MCAT review, treat this species of Interdisciplinary Discussion as a variety of a reading comprehension exercise. These types of discussions (and there are more coming) are designed to deepen your interest and understanding of fundamental concepts by showing them within the kinds of contexts that MCAT passages may present. On the MCAT, almost every question, even after the most dense passages, will depend on fundamental principles, not advanced knowledge.

The WikiPremed MCAT Course is a free comprehensive course in the undergraduate level general sciences. Undergraduate level physics, chemistry, organic chemistry and biology are presented by this course as a unified whole within a spiraling curriculum.

Please read our policies on privacy and shipping & returns.  Contact Us.
MCAT is a registered trademark of the Association of American Medical Colleges, which does not endorse the WikiPremed Course.

Creative Commons License
The work of WikiPremed is published under a Creative Commons Attribution Share Alike 3.0 License. There are elements of work here, such as a subset of the images in the archive from WikiPedia, that originated as GNU General Public License works, so take care to follow the unique stipulations of that license in printed reproductions. You can use the resources here for commercial or non-commercial purposes, but please give attribution and a link to the production credits and edit history of the resource. For the works here which began as my individual work, please attribute "John Wetzel, an author at".