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

Name: Exam Paper Generator | JEE NEET Paper Generator | Vedclass
Brand: Vedclass
Rating: 5 (35 reviews)

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?

Similar Questions

What is obtained when $2-propanol$ is reacted with copper at $300\,^oC$?

The reaction $CH_3-C(CH_3)(OH)-CH_3 \xrightarrow{H_2SO_4} CH_3-C(CH_3)=CH_2$ is an example of:

Consider the following reaction:
$CH_3CH_2OH$ $\xrightarrow{PBr_3} X$ $\xrightarrow{alc. KOH} Y$ $\xrightarrow[(ii) H_2O, \text{heat}]{(i) H_2SO_4, \text{room temperature}} Z$
The product $Z$ is

Write the main product of the given reactions:
$1$. $(CH_3)_2CHCHBrCH_3 \xrightarrow[ethanol]{KOH, \Delta }$
$2$. $(CH_3)_2CHCH(OH)CH_3 \xrightarrow{H_2SO_4, \Delta }$

In $CH_3CH_2OH$,the bond that undergoes heterolytic cleavage most readily is

Vedclass Test Series

Exam Paper Generator

Online Exam Module