This molecule is a phenol, not a hexanol, because the cyclic group has aromatic double bonds
rather than single bonds. The methyl group is separated from the hydroxyl carbon by one carbon
in between, making this molecule m-methylphenol.5 . C
All else being equal, boiling points increase with increasing size of the alkyl chain because of
increased van der Waals attractions. Isobutyl alcohol has the largest alkyl chain and will thus have
the highest boiling point; methanol has the smallest chain and will thus have the lowest boiling
point.6 . B
Phenols have significantly more acidic hydroxyl hydrogens than other alcohols because of
resonance stabilization of the conjugate base, so this will be the most acidic hydroxyl hydrogen.
The acidity of hexanol and cyclohexanol are close, but the hydroxyl hydrogen of hexanol is
slightly more acidic because the ring structure of cyclohexanol is slightly electron-donating,
which makes its hydroxyl hydrogen slightly less acidic.7 . B
CH 3 CH 2 CH 2 OH is 1-propanol, a primary alcohol. The desired end product, CH 3 CH 2 CHO, is
propanal, an aldehyde. Of the available options, the only reactant capable of oxidizing primary
alcohols to aldehydes is pyridinium chlorochromate (PCC). Chromic trioxide and dichromate salts
will both oxidize primary alcohols to carboxylic acids.8 . D
Cyclohexanol is a secondary alcohol, so any of the oxidizing agents listed will convert it to a
ketone.9 . A
Acidic conditions, provided by dilute sulfuric acid, are required to complete the Jones oxidation.
This reaction is carried out in aqueous conditions, eliminating choice (C). While heat may speed
up the reaction, high temperatures are not required for this reaction, eliminating choice (D).10 . A
Methylsulfonyl chloride serves as a protecting group for alcohols, which are converted into
mesylates. Reacting with this reagent before continuing with what would normally be an
oxidation reaction keeps the alcohol from reacting; when the protecting group is then removed