[FictionDurden]

As you can see from the 1st picture, I need two reagents (replacing the question marks) to get from the alkyl halide to the alkoxide. I have worked on this for awhile, and I'm not sure what reagents I need to use!

For the 2nd synthesis, do I use a halide for the first arrow and CH2Cl2 for the second arrow?

[Mitch]

CH2Cl2 is a solvent not necessarily a reagent.

[AWK]

1.
RBr + Mg = RMgBr
RMgBr + C2H4O (ethylene oxide)

2.
a) reduction to double bond (H2 Lindlar catalyst)
b) chlorination of double bond

[maxyoung]

1)
first step: BrMgCH2CH2=CH2/dry ether
second step: i BH3/THF
                   ii H2O2/OH-

epoxide is not a good choice in this case--it adds only two more carbon

[AWK]

Maxyoung is right, I wrongly counted carbon atoms in chain and obtained a shorter carbon chain.

[movies]

Another alternative for 1:

1a) t-BuLi
  b) CuCl
  c) acrolein
2) NaBH₄