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Grade: 11
what is the answer for the given question uploaded?(the marked option isn’t correct) if the reaction has to proceed according to hoffman’s rule(anti-satyzeff’s rule),then shouldn’t the base be as bulky as possible?
8 months ago

Answers : (2)

Vikas TU
8478 Points
Since we must try to get an Hoffman product we must look for the bulkiest nucleophile in the options  which is the teritary carbon with attached ethyl group.
7 months ago
231 Points
To get the least substituted alkene as the major product, following Hofmann elimination, the base must be as bulky as possible, and the base in Option (d) is the bulkiest, having a tertiary carbon surrounded with three ethyl groups.
Now, the only confusion was that, in option (c ), the carbon is tertiary, having the maximum number of hyperconjugative structures. Does this number of hyperconjugative structures (more stability of base) affect Hofmann elimination? I asked my teacher, he said “No”.
Thus, Option (d) is correct, as it’s the bulkiest base. Number of alpha hydrogens does not play any role in favouring Hofmann elimination.
7 months ago
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