CHOOSING THE MOST PROBABLE PATH

Don t Skip Steps—Look for Any Hidden Decision Points Make a Scratch Sheet into an Idea Map Beware of Memorization Watch for Bad Habits Stay on the Pathways Don t Force the Answer If Stuck, Don t Just Stare at the Page, Draw Something on It Recognize the Limits Placed by the Reaction Conditions Beware of Limits That You Place on the Problem If Stuck, Examine The Other Possibilities at Each Decision Point When Done, Always Go Back and Check the Answer Practice, Practice, Practice What Can Be Learned From the Problem and the Methods You Used to Solve It That Would Be Applicable to Other Problems  

Electron Flow Pathway Check, Completeness Check, Media Check, Energetics and Stability Check, Charge and Typo Check 

Understand the System—Look Around and Gather Helpful Information Find Possible Routes—F md the Paths, Explore Short Distances Evaluate and Cross-Check—P ck the Lowest-Energy Route, Cross-Check Repeat the Process 

Helpful Information Can be Derived from the Product Make Sure the Chemical Equation Balances Identify the Carbons That Belong to the Starting Materials within the Product Decide What the Original Nucleophile-Electrophile Pairs Might Have Been Consider Any Reasonable Proton Transfer Generate All the Possible Paths, Then Select the Best If It Does Not Make Sense, It s Wrong 

Electron Flow In Organic Chemistry A Decision-Based Guide To Organic Mechanisms, Second Edition. 

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