How to Predict the Product(s) when the Carbocation Stability Is Not Apparent - Part 1

The carbocation stability is critical to the success of many reactions involving organic compounds.


The stability of a carbocation depends on multiple factors, say, its participation in resonance, presence on a substituted carbon (α─H) or existence in an aromatic ring.

However, there may exist a carbocation promoter and/or some other driving force!

Question:

Predict the major product(s) of the following reaction:



Click/tap to enlarge the image

Solution infographic:



Click/tap to enlarge the image

SN1 = Substitution nucleophilic unimolecular, rt = Room temperature

Are you fond of carbocation stability❓ Let Chemaficionado know in the comments below or at mychemistryhomework@gmail.com❗

References:

(1)    Carbocation. Wikipedia. https://en.wikipedia.org/wiki/Carbocation.
(2)    Wikipedia Contributors. Le Chatelier’s principle. Wikipedia. https://en.wikipedia.org/wiki/Le_Chatelier%27s_principle.

‌(3)    Wikipedia Contributors. Silver nitrate. Wikipedia. https://en.wikipedia.org/wiki/Silver_nitrate.‌

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