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    Carbon Compounds and Acidic Hydrogens

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    You have two carbon containing compounds, nitromethane (CH3NO2) and chloromethane (CH3Cl). The eletronegativities of chlorine and nitrogen are very similar. Even though hydrogens bonded to carbon generally are not very acidic (i.e., pKa's are generally in the 50's), when there are electronegative elements, such as fluorine, chlorine, and nitrogens, bonded to the carbon as well, the hydrogens become much more acidic (pKa's generally in the 20's). Knowing this, which compound, chloromethane or nitromethane, would you expect to have the most acidic hydrogen's? Justify your answer.

    © BrainMass Inc. brainmass.com December 24, 2021, 10:53 pm ad1c9bdddf
    https://brainmass.com/chemistry/bonding/carbon-compounds-acidic-hydrogens-516700

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    CH3NO2 will have the most acidic hydrogens. This is because even though N and Cl have similar electronegativity, N is further attached to 2 O's. O is more electronegative than N. So O will withdraw electron density from N which will further withdraw electron density from C. This weakens the C-H bond making it more acidic than the C-H in CH3Cl.

    This content was COPIED from BrainMass.com - View the original, and get the already-completed solution here!

    © BrainMass Inc. brainmass.com December 24, 2021, 10:53 pm ad1c9bdddf>
    https://brainmass.com/chemistry/bonding/carbon-compounds-acidic-hydrogens-516700

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