Exactly 2.00 g of an ester A containing only C, H, and O was saponified with 15.00 mL of a 1.00 M NaOH solution. Following the s
aponification, the solution required 5.30 mL of 1.00 M HCl to titrate the unused NaOH. Ester A, as well as its acid and alcohol saponification products B and C, respectively, were all optically active. Compound A was not oxidized by K2Cr2O7, nor did compound A decolorize Br2 in CH2Cl2. Alcohol C was oxidized to acetophenone by K2Cr2O7. When acetophenone was reduced with NaBH4, a compound D was formed that reacted with the acid chloride derived from B to give two optically active compounds: A (identical to the starting ester) and E. Propose a neutral structure for each compound that is consistent with the data. Note that the absolute stereochemical configurations of chiral substances cannot be determined from the data. Arbitrarily draw a configuration for an enantiomer (and be consistent with the derivatives); omit wedge/dash bonds for a racemate.
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