Passage Ethanol Is an Important Source of Energy That Is Frequently

Passage
Ethanol is an important source of energy that is frequently used as a supplement to gasoline.  It can be obtained from renewable resources such as the cellulose found in plant matter.  When subjected to a process called gasification, the plant mass is converted to a mixture called syngas, composed predominantly of carbon monoxide and molecular hydrogen.  Syngas can be passed over a rhodium catalyst to generate ethanol and other products.  After using this method, a group of researchers analyzed the resulting products by gas chromatography using helium as a carrier gas.  The results are shown in Figure 1.
Figure 1  Gas chromatograph of syngas catalysis productsMass spectrometry revealed that the process yielded similar amounts of ethanol, acetic acid, and acetaldehyde, with trace amounts of ethane.  In addition, the ethanol peak was found to be contaminated with ethyl acetate.  Another group of researchers in the same laboratory had recently produced Compound 1 as a by-product in a separate reaction.  They combined Compound 1 with purified ethyl acetate to form megestrol acetate, a drug used in the treatment of certain cancers.  This reaction also produced ethanol, as shown in Scheme 1.
Scheme 1
Adapted from Lopez L, Velasco J, Montes V, Marinas A, Cabrera S, Boutonnet M, Järås S. Catalysts  2015.
-During the conversion of Compound 2 to megestrol, why was the secondary alcohol affected, whereas the tertiary alcohol was not?

A) Tertiary alcohols cannot be readily oxidized.
B) The secondary alcohol is stabilized by resonance.
C) The tertiary alcohol is less acidic than the secondary alcohol.
D) Secondary alcohols are better nucleophiles.

Correct Answer:

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