Destroyer OCHEM #28

[plaier]

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DAT destroyer is really sux, never explain enough.

the question OCHEM #28,
the second step with bulky nucleophile will go E2 elimination.
In most E1 and E2 elminations, the product with most substituted double bond will predominate from Zaitsev's rule.
therefore, the answer should be E.

However, the answer in the book is B, and it never explains y it doesnt follow zaitsev's rule.

anyone knows y this question ignores zaitsev's rule?

 

[tranv117]

DAT destroyer is really sux, never explain enough.

the question OCHEM #28,
the second step with bulky nucleophile will go E2 elimination.
In most E1 and E2 elminations, the product with most substituted double bond will predominate from Zaitsev's rule.
therefore, the answer should be E.

However, the answer in the book is B, and it never explains y it doesnt follow zaitsev's rule.

anyone knows y this question ignores zaitsev's rule?

because its a big bulky base, it will undergo Hoffman elimination.

 

[plaier]

because its a big bulky base, it will undergo Hoffman elimination.

Thank you so much. so it goes hofmann rule with less substitutes double bond.

Wait, hofmann reaction need a quaternary ammonium iodide salt.
such as +N(CH3)3

A Bulky base is just E2 elimination. A Bulky base is a favorite nucleophile in E2
E2 will undergo zaitsev'rule

 

[JBarr29]

as a general rule, big bulky bases will cause E2, and eliminate "out." its too big and sterically hindered to eliminate inside. the hoffman rearrangement is not involved here.