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Unformatted text preview: alkynes are readily deprotonated with a strong base like sodium amide. NaNH 2 H + pK a ~ 25 pK a ~ 35 + Na NH 3 © 2006 Gregory R . Cook page 1 Chem 341 North Dakota State University Alkylation of Alkynes Alkyne anions will participate in substitution reactions with carbon-based electrophiles like alkyl halides. Thus, it is relatively straightforward to build up carbon chains by alkylating alkynkes. This works best with primary alkyl halides and methyl halides. While secondary halides may work, they do suffer from side reactions (elimination reactions) and are not ideal. Tertiary halides will not participate in this reaction as they are too hindered for the acetylide to attack it. NaNH 2 H Na H 3 C Br δ + δ-CH 3 © 2006 Gregory R . Cook page 2 Chem 341 North Dakota State University...
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