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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, ˙CH3CH3

A
HCCH<CH2=CH2<CH3CH3<CICH2CH3<FCH2CH3
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B
CH2=CH2<HCCH<CH3CH3<CICH2CH3<FCH2CH3
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C
CH3CH3<CH2=CH2<HCCH<ClCH2CH3<FCH2CH3
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D
CH3CH3<CICH2CH3<FCH2CH3<CH2=CH2<HCCH
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Solution

The correct option is C CH3CH3<CH2=CH2<HCCH<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, FCH2CH3 will have highest acidity followed by ClCH2CH3. 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:
CH3CH3<CH2=CH2<CHCH<ClCH2CH3<FCH2CH3

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