Hydrocarbons, Saytzeff/Hofmann product

The answer is Hofmann product here even though the base is small. I assume its because N(CH3)3 is a poor LG? * Is N(CH3)3+ a poor leaving group? Why/why not? * If it is, what decides whether 'small base' dominates or 'poor LG' dominates?
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22 Replies
iTeachChem Helper
iTeachChem Helper•2w ago
@Dexter
iTeachChem Helper
iTeachChem Helper•2w ago
Note for OP
+solved @user1 @user2... to close the thread when your doubt is solved. Mention the users who helped you solve the doubt. This will be added to their stats.
flower
flower•2w ago
ig cuz it a bulky group
Dexter
Dexter•2w ago
It is a poor leaving group and the reaction mechanism is E1cb In E1cb We always get a hoffman product (most of the times i guess) Small base bulky base is For E2 mech isme mech hi alag hai
trin
trin•2w ago
i had this noted down that NR3+, NO2, CN, COOH and SO3H always give Hoffmann as major product cause of strong -I effect which stabilises carbanion
Nimboi [ping if answering]
wait could u give me a quick summary of favourable conditions and major products for E1, E2 and E1cb
Dexter
Dexter•2w ago
E1 happens in mild acidic medium and requires heating and the reaction is carbocation based. E2 happens in strong basic medium,requires heating and no carbocation or carbanion is formed. E1cb also happens in a strong base,With a poor leaving group ,and Its a carbanion based reaction
Nimboi [ping if answering]
ah ok, saytzeff and hofmann when for each?
Dexter
Dexter•2w ago
E1 E2 saytzeff(mostly) E1cb hoffman
Nimboi [ping if answering]
E1 E2 mein hofmann kab aata hai
Dexter
Dexter•2w ago
E2 mein with bulky base
Nimboi [ping if answering]
alr this makes more sense now
Dexter
Dexter•2w ago
E1 mein when the substrate is bulky
Nimboi [ping if answering]
hm yeah cuz E2 cant function with a poor LG that'd slow the reaction
Dexter
Dexter•2w ago
yeah Man i gotta go for the mock rn ion wanna 😞
Nimboi [ping if answering]
yeah yeah bet lmao aa jao deke
Dexter
Dexter•2w ago
Yeah
Nimboi [ping if answering]
merko toh sirf afternoon mein dena hai i know my shift B)
Dexter
Dexter•2w ago
hiw oh 8th
Dexter
Dexter•2w ago
got it
Nimboi [ping if answering]
hackr ill revise E1cb, apply it to the question and then close doubt

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