reverses the carbon chains, considering the butyl tail to be the esterifying group. Ethers do not
form under these conditions, so choices (B) and (C) are also incorrect.10 . D
The α-hydrogen of a carboxylic acid is relatively acidic as far as organic compounds go, due to
resonance stabilization. However, the hydroxyl hydrogen is significantly more acidic because it is
able to share the negative charge resulting from deprotonation between both electronegative
oxygen atoms in the functional group.
11 . B
The reaction of formic acid, which is a simple carboxylic acid, with sodium borohydride, which is
a mild reducing agent, will result in no reaction, and therefore will result in maintenance of the
carboxylic acid. Sodium borohydride is too mild to reduce carboxylic acids, and therefore cannot
produce the primary alcohols that lithium aluminum hydride, a strong reducing agent, would.
12 . C
5-aminopentanoic acid contains a carboxylic acid and an amine. If this molecule undergoes
intramolecular nucleophilic acyl substitution, it will form a cyclic amide. These molecules are
called lactams. Lactones, choice (B), are cyclic esters, not amides.
13 . A
Butanoic anhydride is an anhydride with two butane R groups. Anhydrides are produced by the
reaction of two carboxylic acids with the loss of a water molecule. Therefore, butanoic anhydride
would be produced by the reaction of two molecules of butanoic acid.
14 . C
Nucleophilic acyl substitutions are favored in basic solution, which makes the nucleophile more
nucleophilic; in acidic solution, which makes the electrophile more electrophilic; and by good
leaving groups. However, strong bases do not make good leaving groups; weak bases do.
15 . D
Based on its name, caprylic acid must be a carboxylic acid. The reaction between a carboxylic
acid and ammonia (NH 3 ) would produce an amide—which is not one of the options listed.
Instead, we should take a look at the type of reaction occurring. The production of an amide from
a carboxylic acid and ammonia occurs through a condensation reaction in which a molecule of
water is removed as a leaving group.