Which of the following best explains why the synthetic route shown below would b

Question

Which of the following best explains why the synthetic route shown below would be unsuccessful? HC C: CH_3 CH_3 Br rightarrow CH_3 CH_2 C CC(CH_3)_3 NaNH_2 (CH_3)_3 CBr The alkynicle anion is not a strong enough nucleophile to react w/1-brom opropane in step 1. Sodium is not a strong enough base to deprotonate the terminal alkyne in step 2. The alkynide anion formed by reaction w/sodium will facilitate an (rather than SN_2) reaction w/t-butyl branicle Both substitution reactions will occur on the some end of the alkynes, making a product different than the one shown. Reaction with sodium will result in formation of primary alkyne.

Explanation / Answer

The correct answers is C) because Secondary and tertiary alkyl halide will give elimination by the E2 mechanism rather then substitution reaction.

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