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Arrange the three types of hydrogens in 1‐ethynyl‐3‐methylbenzene in the order from the most acidic to the least.

1‐ethynyl‐3‐methylbenzene

From my understanding, the hydrogen on methyl would be the most acidic as the negative charge after removing the H would be in resonance.

The next one would be the the ethyne hydrogen because the negative charge after removing it would stay on a sp-carbon. The least acidic H would be the one from the benzene ring as the negative charge would fall on a sp2-carbon.

But the answer says the correct order is: ethyne's H > methyl's H > benzene ring's H. Where am I going wrong?

Arrange the three types of hydrogens in 1‐ethynyl‐3‐methylbenzene in the order from the most acidic to the least.

1‐ethynyl‐3‐methylbenzene

From my understanding, the hydrogen on methyl would be the most acidic as the negative charge after removing the H would be in resonance.

The next one would be the the ethyne hydrogen because the negative charge after removing it would stay on a sp-carbon. The least acidic H would be the one from the benzene ring as the negative charge would fall on a sp2-carbon.

But the answer says the correct order is: ethyne's H > methyl's H > benzene ring's H. Where am I going wrong?

Arrange the three types of hydrogens in 1‐ethynyl‐3‐methylbenzene in the order from the most acidic to the least.

1‐ethynyl‐3‐methylbenzene

From my understanding, the hydrogen on methyl would be the most acidic as the negative charge after removing the H would be in resonance.

The next one would be the the ethyne hydrogen because the negative charge after removing it would stay on a sp-carbon. The least acidic H would be the one from the benzene ring as the negative charge would fall on a sp2-carbon.

But the answer says the correct order is: ethyne's H > methyl's H > benzene ring's H. Where am I going wrong?

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andselisk ♦
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Which Hydrogenhydrogen in 3-ethynyltoluene is the most acidic among these 3?

Structure

The question asks to arrange the 3 Hydrogens in the order from most acidic to least.

Arrange the three types of hydrogens in 1‐ethynyl‐3‐methylbenzene in the order from the most acidic to the least.

1‐ethynyl‐3‐methylbenzene

From my understanding, the Hydrogenhydrogen on methyl would be the most acidic as the negative charge after removing the H would be in resonance. Then the

The next best Hone would be the one from the ethyne hydrogen because the negative charge after removing it would stay on a $sp$ Carbonsp-carbon. And the worst The least acidic H would be the one from the Benzenebenzene ring as the negative charge would fall on a $sp^2$ Carbonsp2-carbon. 

But the answer says the correct order is; Ethyne'sis: ethyne's H > Methyl'smethyl's H > Benzenebenzene ring's H.

  Where am I going wrong?

Which Hydrogen is the most acidic among these 3?

Structure

The question asks to arrange the 3 Hydrogens in the order from most acidic to least.

From my understanding, the Hydrogen on methyl would be most acidic as the negative charge after removing the H would be in resonance. Then the next best H would be the one from the ethyne because the negative charge after removing it would stay on a $sp$ Carbon. And the worst H would be the one from the Benzene ring as the negative charge would fall on a $sp^2$ Carbon. But the answer says the correct order is; Ethyne's H > Methyl's H > Benzene ring's H.

  Where am I going wrong?

Which hydrogen in 3-ethynyltoluene is the most acidic?

Arrange the three types of hydrogens in 1‐ethynyl‐3‐methylbenzene in the order from the most acidic to the least.

1‐ethynyl‐3‐methylbenzene

From my understanding, the hydrogen on methyl would be the most acidic as the negative charge after removing the H would be in resonance.

The next one would be the the ethyne hydrogen because the negative charge after removing it would stay on a sp-carbon. The least acidic H would be the one from the benzene ring as the negative charge would fall on a sp2-carbon. 

But the answer says the correct order is: ethyne's H > methyl's H > benzene ring's H. Where am I going wrong?

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Which Hydrogen is the most acidic among these 3?

Structure

The question asks to arrange the 3 Hydrogens in the order from most acidic to least.

From my understanding, the Hydrogen on methyl would be most acidic as the negative charge after removing the H would be in resonance. Then the next best H would be the one from the ethyne because the negative charge after removing it would stay on a $sp$ Carbon. And the worst H would be the one from the Benzene ring as the negative charge would fall on a $sp^2$ Carbon. But the answer says the correct order is; Ethyne's H > Methyl's H > Benzene ring's H.

Where am I going wrong?