Chemistry Reference
In-Depth Information
to affect this deprotonation. Please note that this same esterification can proceed
under acidic conditions in methyl alcohol.
The second step in this sequence, illustrated below, is a 1,2-addition reaction
between a dimethyl malonate anion and 2-naphthaldehyde. The mechanism for
1,2-addition reactions was discussed in detail in Chapter 7. In order for this reac-
tion to proceed, it is important to use a base that is sufficient to deprotonate the
methylene group of dimethyl malonate. Furthermore, it is important to use a
base that will not hydrolyze the methyl esters. Sodium hydride is generally suffi-
cient to affect this deprotonation.
This molecule is composed of three fragments resembling structures from the
above list of compounds. These fragments are illustrated below and relate to
phenol (hydroxybenzene), allyl bromide, and methyl iodide.
The combination of these compounds will generate the target compound through a
three-step synthetic sequence. In the first step, illustrated below, phenol is alkylated
with allyl bromide through an S
N
2
0
mechanism. The mechanism for an S
N
2
0
reaction was presented in detail in Chapter 4. In this reaction it is important to
