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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: FictionDurden on November 22, 2004, 09:50:18 PM

Title: synthesis
Post by: FictionDurden on November 22, 2004, 09:50:18 PM

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?

Title: Re:synthesis
Post by: Mitch on November 23, 2004, 02:26:30 AM

CH2Cl2 is a solvent not necessarily a reagent.

Title: Re:synthesis
Post by: AWK on November 23, 2004, 03:57:18 AM

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

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

Title: Re:synthesis
Post by: maxyoung on November 23, 2004, 04:21:53 AM

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

Title: Re:synthesis
Post by: AWK on November 23, 2004, 06:12:24 AM

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

Title: Re:synthesis
Post by: movies on November 23, 2004, 05:37:28 PM

Another alternative for 1:

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