Carbonyl oxygen hydrogen bond formation

The carbonylation of alcohols can proceed with formation of carboxylic acid by catalytic insertion of CO into the carbon-oxygen bond. An alternative reaction gives rise to oxalate or formate esters, when the CO is inserted into the oxygen-hydrogen bond. The members of the nickel triad carbonylate alcohols to give each of these products, and they will be discussed separately. 

The relative basicity of carbonyl oxygen atoms can be measured by studying strength of hydrogen bonding between the carbonyl compound and a hydrogen donor such as phenol. In carbon tetrachloride, values of for 1 1 complex formation for the compounds shown have been measured. Rationalize the observed order of basicity. 

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