09. Adding a Functional Group to the End of a Chain Problem

How about the synthesis where we start from a simple alkane and we end up with a more complex molecule featuring a functional group at the very edge of a chain? The problem with syntheses like this one is that we do not have any functional groups in the starting material whatsoever. Which means, we need to add a functional group to our molecule. And the only method we can use here is a radical halogenation. The issue here is that the radical halogenation reaction add a bromine atom to the most substituted atom instead of the place where we need it! So, what are we going to do? We’ll have to move our functional group!

Moving a functional group along the chain is a common sophomore chemistry challenge that you are likely to see in your course. Most commonly, we’re going to use a combination of halogenation and elimination reaction to accomplish this goal.

Reactions that you’re going to use in this synthesis:

  1. Radical halogenation
  2. Elimination
  3. Radical hydrohalogenation
  4. Grignard reaction
  5. Substitution

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