Chemistry Reference
In-Depth Information
Mechanism Summary
Nucleophilic Addition-Elimination (Nucleophilic Acyl Substitution)
-
Nu
+
Nu
R
R
-
-
C
O
R
CO
CO
+
L
L
L
Nu
Learning Objectives
1.
Know the meaning of: carboxylic acid, carboxyl group, acyl group, carboxylate anion,
acidity or ionization constant, inductive effect.
2.
Know the meaning of: carboxylate salt, ester, acyl halide, acid anhydride, primary
amide.
3.
Know the meaning of: Fischer esterification, nucleophilic addition-elimination
(nucleophilic acyl substitution), tetrahedral intermediate, saponification,
ammonolysis, acyl transfer.
4.
Given the IUPAC name of a carboxylic acid, salt, ester, amide, acyl halide, or
anhydride, write its structural formula, and given the structure, write the name.
5.
Know the common names of the monocarboxylic acids listed in Table 10.1 and the
dicarboxylic acids listed in Table 10.2.
6.
Know the systems for designating carbons in a carboxylic acid chain by numbers
(IUPAC) or by Greek letters (common).
7.
Know how to name acyl groups and how to write a formula given a name that
includes acyl group nomenclature.
8.
Given the formula of a carboxylic acid, write an expression for its ionization constant,
K
a
.
9.
Write the resonance structures of a carboxylate anion.
10.
Given two or more carboxylic acids with closely related structures, rank them in order
of increasing (or decreasing) acidities (p
K
a
s).
11.
Tell whether a particular substituent will increase or decrease the acidity of a
carboxylic acid.
12.
Given a carboxylic acid and a base, write the equation for salt formation.
13.
Given a carboxylic acid, tell which aldehyde or primary alcohol is needed for its
preparation by oxidation.
14.
Given an aromatic compound with alkyl substituents, tell which aromatic acid would
be obtained from its oxidation.
