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    Hyrdolysis of NaOH

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    Please see the attached file - for the top figure - I thought NaOH was not suitable because of the steric hindrance.

    And for the 2nd substrate b/c of the ether functional group which tends to resist hydrolysis - but I am confused on this one.

    Why is NaOH not a suitable for hydrolysis in either substrate, I was told to look at the individual functional groups in both substrates and determine whether or not it will hydrolyze with NaOH - I stated my reasons above, does that seem plausible.

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    Solution Preview

    I would propose 2 reasons for the resistance in this case
    (i) Like you say, steric hinderance around the carbonyl group
    (ii) The hydrogen on the carbon circled in red is quite acidic, so instead of attacking the carbonyl, the OH can depronate this hydrogen to form water. The anion from deprotonation can delocalize into the benzene ...

    Solution Summary

    Why NaOH is not suitable for hydrolysis in either substrate are determined.