[kdsammy]

My homework is asking for the synthesis of Acetylene from 1-Cyclohexyl-1-Butanol. In case i spelled something wrong or wrote out the formula incorrectly, here's a picture of the problem:



I'd appreciate any kind of help and pictures would be unbelievably helpful to me.
EDIT: Sorry, I didn't see the forum rules. Here's my attempt, but its kind of a shot in the dark more than anything.




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[AWK]

The first step can be usefull. The rest is not understandable. In the next step you have to break C-C bond between ring and side chain.

[kdsammy]

Okay, so i'd use an epoxide. Would any strong nucleophile be fine? and what would i do afterwards?

[orgopete]

Is this being understood correctly? Although that might be the question, it looks unusual. Is the arrow supposed to be a retrosynthetic arrow, the reverse of what is being asked?

[mjpam]

Is this being understood correctly? Although that might be the question, it looks unusual. Is the arrow supposed to be a retrosynthetic arrow, the reverse of what is being asked?

I have largely the same question. What kdsammy may want to consider is that the "starting" material is rather unfunctionalized: with the exception of the alcohol, all the carbons are about as highly reduced as possible, which, from an introductory organic chemistry perspective, is relatively easy to achieve but much harder to reverse. Without too much more rambling, I'd like to point out that molecules are often much easier to build than they are to selectively tear apart