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(a) Compare the reactivity of Me3CO^(Ө)K...

(a) Compare the reactivity of `Me_3CO^(Ө)K^(oplus)` and `EtNH_2` in `E2` reaction.
(b) Why is `Me_3CO^(Ө)K^(oplus)` superior to `EtO^(Ө)` in `E2` reaction ?
(c) Compare the effectiveness of `Me_3CO^(Ө)K^(oplus)` in `DMSO` and `Me_3COH` as solvents.
(d) `Me_2C C1C H_2 CH_3 overset (Me_3 CO^(Ө)K^*)rarr` Major alkene.

Text Solution

Verified by Experts

(a) `Me_3CO^(Ө)` is more than basic than `EtNH_2`.
`[{:("Acidic character" EtNH_(3)^(oplus) gt Me_(3)COH),("Basic character" EtNH_(2) lt Me_(3)C^(Theta)):}]`
(b) Large size of `Me_3CO^(Ө)` inhibits the `SN^2` reaction.
(c) `Me_3CO^(Ө)` is more reactive in aprotic `DMSO` where it is not solvated. Its effectiveness in `MeCOH` is reduced by H-bonding.
(d)
Less-substituted Hofmann products are formed, because attack by bulky base `(Me_3CO^(Ө))` at `2^@` adjacent `H` atoms gives more-substituted Saytzeff product `(Me_2 C=CH-CH_3)` which is sterically hinderd, Preferential attack is at the less-substituted `1^@ H`.
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