Integrated SequencePhysics Chemistry Organic Biology

WikiPremed Resources

Module 9 in the Syllabus

Electrophilic Addition of HX to Alkenes
Mechanisms and explanations from the Organic Mechanisms Pocketbook

SN1 Mechanism with Alkyl Halides
Mechanisms and explanations from the Organic Mechanisms Pocketbook

E1 Mechanism with Alkyl Halides
Mechanisms and explanations from the Organic Mechanisms Pocketbook

Intramolecular Cationic Rearrangements Images
Image gallery for study with links to larger teaching JPEGs for classroom presentation

Question Drill for Intramolecular Cationic Rearrangements
Conceptual Vocabulary Self-Test

Basic Terms Crossword Puzzle

Basic Puzzle Solution

Conceptual Vocabulary
CarbocationA carbocation is an ion with a positively-charged carbon atom.
Rearrangement reactionA rearrangement reaction is a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule.
Reaction intermediateA reaction intermediate is a molecular entity with a lifetime appreciably longer than a molecular vibration that is formed from the reactants and reacts further to give the products of a chemical reaction.
Markovnikov's ruleMarkovnikov's rule states that with the addition of hydrogen halide to an alkene, the acid hydrogen becomes attached to the carbon with the greatest number of hydrogens, and the halide group becomes attached to the carbon with the fewest number
IntramolecularIntramolecular in chemistry describes a process or characteristic limited within the structure of a single molecule; a property or phenomenon limited to the extent of a single molecule.
Elimination reactionAn elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one or two-step mechanism
SN1 reactionCommonly seen in reactions of secondary or tertiary alkyl halides, the SN1 reaction is a substitution reaction in organic chemistry that involves a carbocation intermediate.
Structural isomerismStructural or constitutional isomerism is a form of isomerism in which molecules with the same molecular formula have atoms bonded together in different orders
Trigonal planarTrigonal planar is a molecular geometry with one atom at the center and three atoms at the corners of a triangle all in one plane.
Friedel-Crafts alkylationFriedel-Crafts alkylation involves the alkylation of an aromatic ring and an alkyl halide using a strong Lewis acid catalyst.
1,2-rearrangementA 1,2-rearrangement or shift is an organic reaction where a substituent moves from one atom to another atom in a chemical compound.
HyperconjugationHyperconjugation is the stabilizing interaction that results from the interaction of the electrons in a sigma bond with an adjacent empty (or partially filled) non-bonding p-orbital or antibonding pi orbital to give an extended molecular orbital that increases the stability of the system.
Neighbouring group participationNeighbouring group participation is the interaction of a reaction center with a lone pair of electrons in an atom or the electrons present in a sigma bond or pi bond.
Non-classical ionNon-classical ions in organic chemistry are a special type of carbonium ions displaying delocalization of sigma bonds in 3-center-2-electron bonds of bridged systems.
Advanced terms that may appear in context in MCAT passages
Carbenium ionA carbenium ion is a carbocation of the trivalent and classical type.
Carbonium ionA carbonium ion is a carbocation of the penta- or tetracoordinated nonclassical type.
Pinacol rearrangementThe pinacol rearrangement is a method for converting a 1,2-diol to a ketone in organic chemistry. In the course of this organic reaction, a carbocation is formed, and an alkyl group migrates to the carbocation center.
Wagner-Meerwein rearrangementA Wagner-Meerwein rearrangement is a class of carbocation 1,2-rearrangement reactions in which a hydrogen, alkyl or aryl group migrates from one carbon to a neighboring carbon.

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".