Acetylide Alkylation | SN2 with Terminal Alkynes | 9.9 Organic Chemistry

Chad covers one of the more important alkyne reactions in this lesson, the alkylation of acetylide ions derived from terminal alkynes. He begins by reviewing the formation of acetylide ions by deprotonating terminal alkynes most commonly with NaNH2 (sodium amide). The resulting acetylide ion is a strong nucleophile and can carry out an SN2 reaction with either a methyl or primary alkyl halide ultimately increasing the length of the carbon chain. This ability to increase the length of the carbon chain is the key to the importance of this reaction as we have relatively few ways to achieve this in organic synthesis.

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00:00 Lesson Introduction
00:21 Review of Acetylide Ion Formation
00:38 Alkylation of Acetylide Ions (SN2)

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