Reactivity of central carbon of Ketone vs Alchohol [closed]








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I am trying to measure the reactivity of the carbon (of C=O and C-OH bonds) as described below. Lets assume the groups $R,R'$ are identical in both molecules.


[![enter image description here](https://i.stack.imgur.com/qnLNh.jpg)](https://i.stack.imgur.com/qnLNh.jpg)


Now I am trying here to to figure out the reactivity of the central carbon towards nucleophilic attack. Now from steric point of view, the ketonic carbon is less hindered, hence more reactive.


Now on charge separation (polarity) point of view, and this is where I am not clear, in case of alcohol, the O-H bond is polar, but to make the central carbon electron deficient the oxygen of O-H group has to pull electrons from $\sigma$ bond which is harder than $\pi$ bond of ketone.


Hence I think central carbon of ketone (all else identical) is more susceptible to nucleophilic attack.


Can someone kindly comment on my reasoning?




You are throwing snippet facts about and refusing to look at a totality. Sure ketone is less hindered [draw more appropriate structures to compare] but do not compare it only to an alcohol but also to an alkene. Next you are concerned about the polarity of the OH making the C-O bond more polar. This is confounding separate things and makes conclusions more difficult. In both cases the Carbon-Oxygen bond is polar with the carbon more positive. Your reasoning makes it at best a draw although thinking about the pi bonds has merit. You must think more about the possible mechanisms of carbonyls and monosubstituted alkanes, the intermediates that might be involved, and the possible transition states. Instead of alcohols consider sulfonate esters


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