Which of the following correctly lists the compounds in order of decreasing acidity

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Which of the following correctly lists the compounds in order of decreasing acidity

[From: ] [author: ] [Date: 13-09-25] [Hit: ]

Thus, the proton bonded to each C is somewhat easy to remove. I would say it is easier to deprotonate acetylene (HCCH) than ethane because of this.Hope this gives you some insight!......

a) H2O > HC≡CH > NH3> CH3CH3
b) HC≡CH > H2O > NH3> CH3CH3
c) CH3CH3 > HC≡CH > NH3> H2O
d) CH3CH3 > HC≡CH > H2O > NH3
e) H2O > NH3> HC≡CH > CH3CH3

I know the answer is A, but can anyone give a brief explanation, especially regarding the HC≡CH bond? Thanks

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One way to look at is to think about pH.... you know ammonia (NH3) is basic, and organic compounds are not very acidic... water can act as an acid or a base. The C-C triple bond is fairly stable. Thus, the proton bonded to each C is somewhat easy to remove. I would say it is easier to deprotonate acetylene (HCCH) than ethane because of this.

Hope this gives you some insight!

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