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Organic chemistry reagent question? Br2/ 2-3 equivs of NaNH2/ NH3 (l) what does it do?

Organic chemistry reagent question?

Br2/ 2-3 equivs of NaNH2/ NH3 (l) what does it do?

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Answer #1

NaNH2 is a strong base and excellent nucleophile. It’s used for deprotonation of weak acids and also for elimination reactions.

An application of NaNH2 happens in the formation of alkynes from halogens. Treatment of either geminal dihalides (i.e. – two halogens on one carbon) or vicinal dihalides (halogens on adjacent carbons) with NaNH2 (2 equiv) will result in the formation of alkynes.

Since vicinal dihalides are easily made by the reaction of alkenes with halogens such as Br2 or I2, this is a useful way of converting alkenes to alkynes.

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