EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
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An unknown compound A of molecular formula C10H18O reacts with H2SO4 to form two compounds (B and C)of molecular formula C10H16. B and C both react with H2 in the presence of Pd-C to form decalin. Ozonolysis of B forms D, and ozonolysis of C forms a diketone E of molecular formula C10H16O2. Identify the structures of compounds A, B, C, and E.
Enanthotoxin is an extremely poisonous organic compound found in hemlock water drop-
wart, which is reputed to be the most poisonous plant in England. It is believed that no
British plant has been responsible for more fatal accidents. The most poisonous part of
the plant is the roots, which resemble small white carrots, giving the plant the name"five
finger death."Also poisonous are its leaves, which look like parsley. Enanthotoxin is thought
to interfere with the Nat current in nerve cells, which leads to convulsions and death.
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How many stereoisomers are possible for enanthotoxin?
A chiral amine A having the R configuration undergoes Hofmann elimination to form an alkene B as the major product. B is oxidatively cleaved with ozone, followed by CH3SCH3, to form CH2 = O and CH3CH2CH2CHO. What are the structures of A and B?
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