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Writing Reaction Mechanisms

Topic Review on "Title":

Mechanisms Basics
Each step should involve no more than two molecules, ions, or radicals.  Arrows flow one way and follow each other consecutively.  Each species is a reactant or a product from an earlier step.  Each step must be balanced in terms of atoms, electrons, and charges.  A mechanism is a description of starting materials to products.

Arrow Drawing Skills
A double headed arrow shows movement of a pair of electrons.  Arrows are drawn from an unshared or shared electron pair (tail of arrow) to new location of electron pair (head of arrow).  Draw arrow from electron-rich species (nucleophile) to electron-poor species (electrophile).  Nucleophiles have negative charges or have an unshared electron pair.  A single headed arrow shows movement of a single electron and is used for radicals.  The arrow is drawn from a single radical to form a new bond.

Movement of Arrows with Electrons
An unshared electron pair becomes a shared electron pair.  A shared electron pair becomes an unshared electron pair.  A shared electron pair becomes another shared electron pair.

Intermediates can only come from starting reagents.  Do not generate a species because you think it belongs there!  Good intermediates include stable intermediates, conjugate acids or bases of reactants or products, neutral intermediate compounds, neutral organic molecules, carbocations, carbanions, free radicals, or carbenes.  Characteristics of unlikely intermediates include two negative charges on the same molecule; two positive charges on the same molecule; opposite charges on the same molecule, except for recognized species; more than eight electrons on a first row element; or first row element with less than six electrons.

Rapid Study Kit for "Title":
Flash Movie Flash Game Flash Card
Core Concept Tutorial Problem Solving Drill Review Cheat Sheet

"Title" Tutorial Summary :

Understanding mechanisms is the key to understanding reactions.  Arrow drawing skills include the arrows for heterolytic and homolytic bonds.  Examples of nucleophiles are given.  An unshared electron pair becomes a shared electron pair.  A shared electron pair becomes an unshared electron pair.  A shared electron pair becomes another shared electron pair.  Intermediates can be described in terms of formation of intermediates, characteristics of good intermediates, and characteristics of unlikely intermediates.

Tutorial Features:

This tutorial provides the comprehensive coverage of the chapter with easy introduction and simple illustration. It features:

  • Concept map showing interconnections of new concepts in this tutorial and those previously introduced.
  • Definition slides introduce terms as they are needed.
  • Visual representation of concepts.
  • Use of colors to emphasis points.
  • Explanations of arrows and how they move.
  • Examples worked out step-by-step throughout the tutorial.
  • A concise summary is given at the conclusion of the tutorial.

"Title" Topic List:

Mechanisms Basics

  • Understanding Mechanisms

Arrow Drawing Skills

  • Basic Arrow Drawing Skills for Heterolytic Bonds
  • Examples of Nucleophiles
  • Basic Arrow Drawing Skills for Homolytic Bonds

Movement of Electrons with Arrows

  • An Unshared Electron Pair Becomes a Shared Electron Pair. 
  • A Shared Electron Pair Becomes an Unshared Electron Pair. 
  • A Shared Electron Pair Becomes another Shared Electron Pair.


  • Formation of Intermediates
  • Characteristics of Good Intermediates
  • Characteristics of Unlikely Intermediates

See all 24 lessons in college chemistry, including concept tutorials, problem drills and cheat sheets:
Teach Yourself Organic Chemistry Visually in 24 Hours

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