I'm sorry to bother you guys again. My teacher asked me to draw ALL possible sets of answers for the following question, but I still can't draw them all. Please help me.
Compound A (C6H6O6) is an acyclic tribasic acid isolated from the leaves and tubers of Aconitum napellus. Hydration of A gives two isomeric compounds, B and D. B is achiral, but D is chiral. Deduce the structures of A, B and D.
All I drew were:
A: HOOC COOH
C=C
H CH2COOH
B: COOH
HOOC-CH2-C-OH
CH2COOH
D: HOOC COOH
HO-C*-*C-H
H CH2COOH
Please *delete me*