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Question

How many of the reagents listed below would give effervercence, when treated with propyne?
(I) NaOH (II) CH3CH2ONa
(III) NaH (IV) NaNH2
(V) NaHCO3 (VI) {(CH3)2CH}2NLi
(VII) CH3CH2Li

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Solution

Effervescence is the formation of gas bubbles in a liquid. It is the escape of gas from an aqueous solution by the chemical reaction.
(I) NaOH does not react with propyne since the alkynes are weak acids.
(II) Sodium methoxide (NaOCH3) is not a strong enough base to deprotonate the terminal alkyne.
(III) NaH reacts with propyne liberating H2.
Hence, it gives effervescence.
NaH+CH3CCHCH3CCNa+H2
(IV) Propyne reacts with NaNH2 evolving ammonia.
(V) Acids only give brisk effervescence with NaHCO3 by evolving CO2 from the carboxylic acids.
(VI) & (VII) Lithium diethylamide is a weaker base than ethyl lithium. Both react with propyne giving no effervescence.
Hence, only NaH,NaNH2 are the correct choices here.

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