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Wrapup: The Quick N’ Dirty Guide To SN1/SN2/E1/E2

The previous several posts dealt with an approach to solving substitution and elimination problems that can only be described as a Quick N’ Dirty Guide to SN1/SN2/E1/E2. The basic premise is this: given 15-20 minutes to describe the basic principles by which one could figure out if a given reaction goes down one of these pathways, these are, in my opinion, the key factors to consider.

Quick N’ Dirty rules, by their nature,  do not cover exceptions. To learn about some of the exceptions, I advise you to go back and read the individual posts [One Two Three Four]. Even further back, I urge you to understand the key concepts behind each reaction, such as nucleophilicity, leaving group ability, carbocation stability, and the mechanism of each of these reactions.

Finally, I will preface this by saying that the best way to learn and understand how these reactions work is to do a lot of practice problems and pay particular attention to situations where you get the wrong answer – they are instructive.

Here goes:

Question 1: Is the carbon containing the leaving group methyl (only one carbon), primary, secondary, or tertiary?

Question 2: Does the nucleophile/base bear a negative charge?

Question 3: Is the solvent polar protic or polar aprotic?

Question 4: Is heat being applied to the reaction?

Writing this post makes me feel like a nun giving out condoms.  I realize there will be many who are reading this an hour before their exam and are completely clueless on this subject. All I have to say is, God help you. And do more fricking practice problems so you don’t put yourself in this situation next time.

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