Sn2 reactions steric hindrance

Although nucleophilic substitution with acetylide anions is a very valuable carbon-carbon bondforming reaction, it has the same limitations as any Sn2 reaction. Steric hindrance around the leaving group causes 2° and 3° alkyl halides to undergo elimination by an E2 mechanism, as shown with 2-bromo-2-methylpropane. Thus, nucleophilic substitution with acetylide anions forms new carbon-carbon bonds in high yield only with unhindered CH3X and 1 ° alkyl halides. 

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See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

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