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JEE Advanced levelNumerical answerDifficulty 3 of 3hc239

The bromoalkane shown is mixed with bromomethane and 1-bromopropane and treated with sodium in dry ether. Assume all coupling combinations occur and ignore alkenes. How many different alkanes are formed (count distinct compounds)? Give the answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 5

The compound shown is bromoethane. With three halides (Me, Et, Pr) there are six couplings: Me-Me ethane, Me-Et propane, Me-Pr butane, Et-Et butane, Et-Pr pentane and Pr-Pr hexane. Me-Pr and Et-Et give the same compound, butane, so the distinct alkanes are ethane, propane, butane, pentane and hexane: 5.
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