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Q.

How many of the following will not show tautomerism?

a) CH3CH2CH2CH2NO2   b) (CH3)2CHCH2NO2    c) CH3CH|NO2CH2CH3  d) (CH3)3CNO

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answer is 3.

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Detailed Solution

d,f,g do not show tautomersim due to absence of alpha hydrogen. If the compound has no `alpha` hydrogen on a saturated carbon next to the keto group or CN or Nitro or oxime group then it cant show tautomerism.Aromatisation/hydrogen bonding is the driving force to convert keto form to enol form.

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