Which base is strong enough to convert (CH_3) | vedclass

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Question

(D) To convert $(CH_3)_3COH$ (tert-butyl alcohol) into $(CH_3)_3CONa$ (sodium tert-butoxide),we need a base stronger than the tert-butoxide ion itself

Vedclass · Accepted Answer

More than one of the above

Vedclass · Answer

(D) To convert $(CH_3)_3COH$ (tert-butyl alcohol) into $(CH_3)_3CONa$ (sodium tert-butoxide),we need a base stronger than the tert-butoxide ion itself. The $pK_a$ of $(CH_3)_3COH$ is approximately $18$. $1$. $NaNH_2$ (sodium amide) contains the amide ion $(NH_2^-)$,which is the conjugate base of ammonia ($NH_3$,$pK_a \approx 38$). Since $38 > 18$,$NaNH_2$ is a much stronger base than the tert-butoxide ion and will drive the reaction to completion. $2$. $CH_3CH_2Na$ (ethylsodium) contains the ethyl carbanion $(CH_3CH_2^-)$,which is the conjugate base of ethane ($C_2H_6$,$pK_a \approx 50$). Since $50 > 18$,it is also a much stronger base than the tert-butoxide ion and will drive the reaction to completion. $3$. $NaOH$ is a weaker base than the tert-butoxide ion,so it cannot convert the alcohol to the alkoxide effectively. Since both $NaNH_2$ and $CH_3CH_2Na$ are strong enough,the correct answer is 'More than one of the above'.

Which base is strong enough to convert $(CH_3)_3COH$ into $(CH_3)_3CONa$ in a reaction that goes to completion?

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