Chromic acid oxidation of aldehydes and primary alcohols

![enter image description here](https://i.stack.imgur.com/A5meF.png)


The answer has to be both A and D. Chromic acid is a strong oxidizer and will take both aldehydes and primary alcohols to carboxylic acids.


However the computer thinks otherwise. Am I just missing something really simple here?




There are many $\ce{CrO3}$ oxidation reagents ([Jones](http://en.wikipedia.org/wiki/Jones_oxidation), [Sarett](http://en.wikipedia.org/wiki/Sarett_oxidation), [Collins](http://en.wikipedia.org/wiki/Collins_reagent), [PCC](http://en.wikipedia.org/wiki/Pyridinium_chlorochromate), etc.), however, most are selective and stop the oxidation of a primary alcohol at the aldehyde stage. On the other hand, the Jones reagent is relatively unselective and will oxidize a primary alcohol to the corresponding carboxylic acid - **if** enough reagent is present. It takes two-thirds of an equivalent of Jones reagent to oxidize one equivalent of the alcohol to the aldehyde and an additional two-thirds equivalent to oxidize the aldehyde to the acid. Also the Jones oxidation is run under acidic conditions (typically dilute sulfuric acid).


I would have though that A, B (the gem-diol will equilibrate with the aldehyde under acidic conditions) and D were correct answers. It seems like the computer answer is either in error or it is a "trick" question (seems unlikely for computer-based learning). The "trick" would be that since an excess of reagent was not specified only 1 equivalent is assumed. Therefore there is not enough reagent to carry out two sequential oxidations; as a consequence only the aldehyde or gem-diol could be **completely** oxidized with one equivalent of reagent. But then A or B is not an acceptable answer either.


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