How do I convert $\ce{CH3CH2OH}$ (ethanol) to $\ce{CH3CH2C#CH}$ (but-1-yne) ?
I'm not too good with reaction mechanisms and conversions are beyond me.
My Attempt:
I've searched through a couple of textbooks and notes and I don't see any direct way to do the reaction.
I think I can use thionyl chloride to to convert from alcohol to chloroalkane: $$\ce{CH3CH2OH + SOCl2 -> CH3CH2Cl + HCl + SO_2\uparrow}$$ The $\ce{SO2}$ escapes but I'm not sure how I can get rid of the $\ce{HCl}$.
Assuming that I do get rid of it somehow, I can take the resulting chloroalkane and add an alkynyl group to it hence forming the required higher alkane. $$\ce{CH3CH2Cl + C2HNa + NaCl -> CH3CH2C#CH + \dots}$$
Again, the mechanism of these reactions elude me. I've only figured out the above from randomly stated properties of reagents. A detailed method of the conversion would be helpful.