SN2 reaction with alkyl bromide and pentanenitrile?
It appears that you are having some difficulty with this synthesis. The suggestion in the Comments that you employ lithium diisopropylamide (LDA) to generate the anion of a nitrile is a wise one. The anion is usually formed a -78oC in tetrahydrofuran (THF). The bromide is added and the reaction mixture is allowed to warm to ambient temperature. There are two possible bonds that can be made in what is termed a retrosynthetic analysis. One by method A and another by method B. The bonds formed are shown in red in structures 2. Method A is better than method B because an SN2 reaction is being conducted on a primary halide, ethyl bromide. Method B requires an SN2 reaction on a secondary halide, 2-bromopropane, a process that is hindered and in competition with an E2 elimination that would produce propene 4 and the starting nitrile 3. Nitrile 2 must be a racemate given its method of formation. It is comprised of equal amounts of the two enantiomers, (R)-2 and (S)-2. By the methods employed here, a single enantiomer cannot be formed. Thus, a &quot;normal bond&quot; (not dashed nor bold) is shown in nitriles 2.