The following pseudo-syntheses (guaranteed not to work) exemplify a common conceptual error.

(a)What is the conceptual error implicit in these syntheses?

(b)Propose syntheses that are more likely to succeed.

The branch of chemistry deals with the synthesizing of organic compounds using some simple molecules called starting materials.

Starting materials are commercially available, and the molecule is simple. The simpler the molecule, the easier will be the mechanism of the reaction.

In this reaction, a bromoalkane is subjected to heat followed by treatment with salt. It results in the formation of methoxy alkane.

The second reaction is the treatment of an alcohol with an acid that results in the formation of a methoxy group attached to alkane.

The two reactions show that the incompatible conditions or reagents can coexist. For the first reaction, S_N1 conditions are not compatible withS_N2 conditions with sodium methoxide.

The tertiary carbocation in the first step will not remain until sodium methoxide addition in the second step. This is a conceptual error.

The second reaction shows the acidic condition in the first step, which is incompatible with the basic condition in the second step. If it is a basic sodium methoxide, it undergoes a neutralization reaction by giving methanol.

This is the conceptual error in the second reaction. So, there is no reaction.

The possible synthesis is given below.

The possible syntheses are given below.