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JEE Advanced levelSingle correct optionDifficulty 3 of 3g2131

An amide $RCONH X_{2}$ has N-H $p K_{a} \approx 17$ . Which of the following bases deprotonates it essentially completely (conjugate acids: $H X_{2} O$ 15.7, $C X_{2} H X_{5} OH$ 15.9, $H X_{2} CO X_{3}$ 6.4, $H X_{2}$ 35)?

A $NaOH$
B $NaOC X_{2} H X_{5}$
C $NaHCO X_{3}$
D $NaH$

Answer: D

lo g K

for

NaH

= 35 - 17 = 18

. For

NaOH

= 15.7 - 17 = - 1.3

, for

NaOEt

= 15.9 - 17 = - 1.1

, for

NaHCO X_{3}

= 6.4 - 17 = - 10.6

. Only

NaH

gives complete deprotonation.

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