[sector9tahiti]

Describe a sequence of reations by which CH₃CH₂CH₂COCH₂CH₃ can be straightforwardly prepared from but-1-yne.

[azmanam]

what do you have so far?  what reactions do you know of alkynes?

[sector9tahiti]

all i got was that you need NaNH₂ to start with and then Br attached to a carbocation.. i think

[azmanam]

1) what does a terminal alkyne and NaNH2 give you as an intermediate?

2) do you have chemsketch or some such program?  It might help as we go along to draw some of these out

http://www.acdlabs.com/download/chemsketch/

3) am i reading your q right?  is this what the question is asking?

[sector9tahiti]

yes you are drawing right... my big problem is not drawing them cause i can do that... i just dont get how to put an oxygen in while still getting rid of the triple bond and making it single

[azmanam]

ok, let's take those very important issues one at a time...

name a few ways to transform a triple bond into a single bond (forward synthesis)

name a few ways to make an ether.  What are the reagents needed in some ether-forming reactions. (retrosynthesis)

then later we'll join the forward and retro synthesis and see if we can't synthesize this ether.

[sector9tahiti]

adding H₂, or HX, or X₂... to make an ether i think you would first add NaNH₂, then add in an R group like BrCHOCH₃. am i on the right track

[azmanam]

good, good.  those are all good ways to transform the triple bond, and an ok way to make an ether... but I didn't say a triple bond needed to be one of the reagents to make an ether.  what other ways do you know to make an ether that doesn't start with a triple bond.

[sector9tahiti]

i dont know

[azmanam]

start here

http://www.cem.msu.edu/~reusch/VirtTxtJml/alcohol2.htm#ethrx1

[sector9tahiti]

i still dont know

[sector9tahiti]

can someone help me get an answer

[aldoxime_amine]

Please read this article ----> http://en.wikipedia.org/wiki/Williamson_ether_synthesis completely.

[sjb]

yes you are drawing right....

But butyl propyl ether is not CH₃CH₂CH₂COCH₂CH₃, so I'm a little confused.

Can you check the name and the structure of your desired compound?

S

[Borek]

Ether or ketone?