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$$\ce{C5H11Cl + C4H9I + 2Na ->}$$ Is this possible in a Wurtz reaction? I want to add 2 different alkyl halides with two different halogens. I'm curious if two different types of halogen on the alkyl reactants is possible.

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  • $\begingroup$ This is going to be pretty messy. Each reagent will react not only with the other one, but also with itself. $\endgroup$ – Ivan Neretin Apr 11 '17 at 14:48
  • $\begingroup$ As a side note, I would also mention the Corey-House synthesis, a method to couple asymmetrical halides. We transform one of the alkyl halides into a lithium dialkyl cuprate (R2CuLi) and react it with the other alkyl halide (R'X). The result would be a alkane R-R'. $\endgroup$ – Pritt says Reinstate Monica Apr 12 '17 at 2:07
  • $\begingroup$ There are going to be issues concerning separation as the products will have nearly same boiling points making fractional distillation difficult. $\endgroup$ – Raghav Apr 12 '17 at 3:55
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The alkyl groups mentioned could be primary, secondary or tertiary The last one's will not be going by Wurtz reaction (these will rather undergo elimination to give alkenes); only primary & secondary can. Even here, we can have a mixture of products:enter image description here

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