Deduce the structure of each compound from the information given. All unknowns in this problem have molecularformula C8H12.(a) Upon catalytic hydrogenation, unknown W gives cyclooctane. Ozonolysis of W, followed by reduction with dimethylsulfide, 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 dimethylsulfide, gives two equivalents of butanedial, O“CH¬CH2CH2¬CH“O. Draw the structure of X.(c) Upon catalytic hydrogenation, unknown Y gives cyclooctane. Ozonolysis of Y, followed by reduction with dimethylsulfide, 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 aone-carbon aldehyde (¬CHO) group on C2. Draw the structure of Z.
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¬CH2CH2¬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 reduction
with dimethyl sulfide, gives a cyclobutane with a three-carbon
one-carbon aldehyde (¬CHO) group on C2. Draw the structure of Z.
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