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BedokFunlandJC

For the hydrolysis of the lactone (ie. cyclic ester) and phenate ester, it is simply the alkaline hydrolysis of ester mechanism. Google it out, read and understand the mechanism (required for H3 Chem but useful-to-know for H2 Chem). If necessary, ask to go through the drawing of the mechanism during tuition.

If you're lazy and don't wish to go through the mechanism, then the inferior H2 Chem way (as opposed to the superior H3 Chem way of being aware of and understanding the mechanism) is to simply use pattern recognition of hydrolysis and change the R1COOR2 (ester) to R1COOH (carboxylic acid) and R2OH (alcohol). Then since you're using NaOH alkaline hydrolysis, deprotonate the acidic R1COOH into R1COO^- Na^+.

As you should already know, alcohols cannot be not deprotonated by the hydroxide OH^- ion, since the alkoxide RO^- ion (ie. conjugate base of alcohol) is even more unstable than the hydroxide OH^- ion.

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