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Mobile App Chapter 9: Q40P (page 432)
You were told in Section 7.11 that is best to use a methyl halide or a primary alkyl halide for the reaction of an acetylide ion with an alkyl halide. Explain why this is so.
Short Answer
The methyl or primary alkyl halide is used for the reaction of an acetylide because it follows substitution through SN2 path and in this case for the backside attack, the halide should be primary to avoid steric hindrance.
Step by step solution
Definition of acetylide ion
The conjugate base of alkyne is called acetylide ion.
R-C≡C- is an acetylide ion.
Reason of using primary alkyl halide
The combination of acetylide and primary alkyl halide forms the desired product through SN2 reaction. This mechanism is called alkylation. As it goes through the SN2 path and the alkyne group is itself bulky in size, back side attack will be hindered in case of bulky alkyl bromide group and this is why, primary alkyl halides are preferred for alkylation reaction.
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