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QUESTION

# Of 2-bromo-3-methylbutane , 2-chlorobutane , 2-chloro-2-methylpropane, which haloalkanes will give 3,4-dimethylhexane when treated with sodium metal (Wurtz reaction)? Write the reaction equation?

You could solve this problem by writing the equation for each reactant, and seeing which one gives the desired product.

It is often easier to do a retrosynthesis.

That is, we work backwards from the products to figure out what the starting materials must be.

The Wurtz synthesis is

"R-X + 2Na" → "R-R + 2NaX"

So, we could write

"R-R" ⇒ "R-X + X-R" (⇒ means "implies" or "can be made from").

For your problem, we could write

"CH"_3"CH"_2"CH(CH"_3")-CH(CH"_3")CH"_2"CH"_3 ⇒ "CH"_3"CH"_2"CH(CH"_3")-X" + "X-CH(CH"_3")CH"_2"CH"_3

If you look at the list of starting materials, yours must be "CH"_3"CH"_2"CH(CH"_3")-Cl", 2-chlorobutane.

The equation for the reaction is then

"CH"_3"CH"_2"CH(CH"_3")-Br" + "2Na" + "Br-CH(CH"_3")CH"_2"CH"_3 → "CH"_3"CH"_2"CH(CH"_3)"-CH(CH"_3")CH"_2"CH"_3