Deduce the structure of each compound from the information given. All unknowns in this problem have molecular formula
C8H12.
(a) Upon catalytic hydrogenation, unknown W gives cyclooctane. Ozonolysis of W, followed by reduction with dimethyl sulfide, gives octanedioic acid, HOOC-(CH2)6-COOH. Draw the structure of W.
(b) Upon catalytic hydrogenation, unknown X gives cyclooctane. Ozonolysis of X, followed by reduction with dimethyl sulfide, gives two equivalents of butanedial, O CH-CH2 CH2-CH O. Draw the structure of X.
(c) Upon catalytic hydrogenation, unknown Y gives cyclooctane. Ozonolysis of Y, followed by reduction with dimethyl sulfide, gives a three-carbon dialdehyde and a five-carbon dialdehyde. Draw the structure of Y.
*(d) Upon catalytic hydrogenation, unknown Z gives cis-bicyclo[4.2.0]octane. Ozonolysis of Z, followed by reductionwith dimethyl sulfide, gives a cyclobutane with a three-carbon aldehyde (-CH2-CH2-CHO) group on C1 and a one-carbon aldehyde (-CHO) group on C2. Draw the structure of Z.