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Question
Arrange the following in increasing order of acidity considering 'H' atom on ∗ carbon atoms.
HC≡˙CH, ˙CH2=2CH2 CICH2 ˙CH3, FCH2˙CH3, ˙CH3−CH3
Arrange the following in increasing order of acidity considering 'H' atom on ∗ carbon atoms.
HC≡˙CH, ˙CH2=2CH2 CICH2 ˙CH3, FCH2˙CH3, ˙CH3−CH3
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Solution
The correct option is C CH3−CH3<CH2=CH2<HC≡CH<ClCH2CH3<FCH2CH3
For more acidity, the negative charge on carbon, after the proton is removed, should be more stable. For this, a group showing −I effect is favourable. Hence, F−CH2CH3 will have highest acidity followed by Cl−CH2CH3. Considering sp,sp2 & sp3 hybridization of carbon, order of electronegativity is sp>sp2>sp3. Hence this is order of the negative charge being stable on the carbon.Hence the required order is:CH3−CH3<CH2=CH2<CH≡CH<ClCH2CH3<FCH2CH3
For more acidity, the negative charge on carbon, after the proton is removed, should be more stable. For this, a group showing −I effect is favourable. Hence, F−CH2CH3 will have highest acidity followed by Cl−CH2CH3. Considering sp,sp2 & sp3 hybridization of carbon, order of electronegativity is sp>sp2>sp3. Hence this is order of the negative charge being stable on the carbon.
Hence the required order is:
CH3−CH3<CH2=CH2<CH≡CH<ClCH2CH3<FCH2CH3
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