Carbon-oxygen double bonds molecular hydrogen

Examination of the molecular formula C14H2602 reveals that the compound has an index of hydrogen deficiency of 2. Because we are told that the compound is a carboxylic acid, one of these elements of unsaturation must be a carbon-oxygen double bond. The other must be a carbon-carbon double bond because the compound undergoes cleavage on ozonolysis. Examining the products of ozonol-ysis serves to locate the position of the double bond. 

Hydrogenation of ketones in alkaline medium at room T and atmospheric P, catalyzed by [Rh(2,2 -bipyridine) (diene)]PFg type complexes occurs with selectivity for reduction of carbon-oxygen double bonds to hydroxyl groups even in the presence of olefinic bonds. The system acts as a hydrogenolysis catalyst for molecular O2, and hydrogenation activity is retained even if large amounts of 62 are present. ... 

First, draw the functional group of an aldehyde and add the remaining carbons, which in this case may be bonded in two different ways. Then, add seven hydrogens to complete the four bonds of each carbon and give the correct molecular formula Note that the aldehyde group may be written showing the carbon-oxygen double bond as C=0, or, alternatively, it may be written —CHO. 

A fourth HMBC correlation is detected between the methylene protons N and the most deshielded carbon. That carbon (Ci) appears to be an ester carbonyl from its chemical shift (8 173.0, Section 3-5c) and exhibits a second connectivity to H. This correlation is crucial because it is the only one that connects Ci indirectly to C9 (via an oxygen as an isovaleryl ester group) of the presumptive cyclohexene fragment. If the connection is confirmed, the molecular fragment 8-1 (with HMBC connectivities shown) accounts for three units of unsaturation and 12 carbons (including the previously surmised carbon-carbon double bond), 17 hydrogens, and 2 oxygens. 

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