Citral, \(\mathrm{C}_{10} \mathrm{H}_{16} \mathrm{O}\), is a terpene that is the
major constituent of lemongrass oil. It reacts with hydroxylamine to yield a
compound of formula \(\mathrm{C}_{10} \mathrm{H}_{17} \mathrm{ON}\), and with
Tollens' reagent to give a silver mirror and a compound of formula
\(\mathrm{C}_{10} \mathrm{H}_{16} \mathrm{O}_{2}\). Upon vigorous oxidation
citral yields acetone, oxalic acid \((\mathrm{HOOC}-\mathrm{COOH})\), and
levulinic acid \(\left(\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{CH}_{2}
\mathrm{COOH}\right)\).
(a) Propose a structure for citral that is consistent with these facts and
with the isoprene rule.
(b) Citral has two isomers, geranial and neral, which yield the same oxidation
products. What is the most likely structural difference between these two
isomers?
(c) Geranial is obtained by mild oxidation of geraniol; neral is obtained in a
similar way from nerol. On this basis assign structures to geranial and neral.