10. Addition Reactions
Ozonolysis
6:32 minutes
Problem 9.43c-d
Textbook Question
Textbook QuestionDeduce the structure of each compound from the information given. All unknowns in this problem have molecular formula C8H12.
(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 aldehyde (-CH2-CH2-CHO) group on C1 and a one-carbon aldehyde (-CHO) group on C2. Draw the structure of Z.
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