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Answer: Propose an efficient synthesis for the following

Chapter 18, Problem 18.65

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QUESTION:

Propose an efficient synthesis for the following transformation: CH3 O CH3 CH3

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QUESTION:

Propose an efficient synthesis for the following transformation: CH3 O CH3 CH3

ANSWER:

Step 1 of 3

Free-radical halogenation of the starting material is accomplished by heating it with NBS in an inert solvent. This produces a benzylic bromide intermediate, which (when treated with a strong unhindered base such as sodium ethoxide) undergoes an elimination reaction to form a terminal alkene.

     

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