Planning a Grignard synthesis

When we plan a Grignard synthesis, we must also take care that any aldehyde, ketone, epoxide, or ester that we use as a substrate does not also contain an acidic group (other than when we deliberately let it react with a terminal alkyne). 

The final product can come from reaction of a suitable reagent such as SOCI with 4-heptanol. This, in turn, can come from a Grignard synthesis. Here is an outline of the retrosynthetic plan. 

The very reactivity that makes a Grignard reagent so useful strictly limits how we may use it. We must keep this reactivity in mind when we plan the experimental conditions of the synthesis, when we select the halide that is to become the Grignard reagent, and when we select the compound with which it is to react. 

The complexities of their constitution in solution make studies of the mechanism of reactions of organomagnesium compounds extraordinarily difficult. Few reactions have stimulated such a wealth of elegantly planned and meticulously executed experiments as those of Grignard reagents with carbonyl compounds (see Section 6.1). Fortunately an admittedly grossly oversimplified rationale for the reactivity of organomagnesium compounds, and in particular for the influence of solvation, is adequate for most applications in organic synthesis. In a monomeric, unsolvated species (2),... 

---