How to Solve a Complex Multi-Step Organic Chemistry Problem?

[nydream12]

Multi-step Organice problem!

Hello, I have a multi-step problem that I can't even begin to solve. I would be really helpful if anyone showed me a way to solve this problem. Thank you. Have a pleasant great day.

Multi-step example:

CH3CH2CH2CH2OH ----> CH3CH2C≡CH

 

[chemisttree]

What reactions do you know of that produce (terminal) alkynes? That is where you need to start.
You are going to kick yourself when you see how easy this problem is.

 

[nydream12]

Would it be Hydration-electrophilic addition of water (1. H20, 2. H2SO4 & HgSO4)? If yes, I don't see how.

 

[chemisttree]

Go the other way first...

 

[nydream12]

CH3CH2CH2CH2OH 1.BH3 2. H2O2,HO > CH3CH2CH=CH2 H2 > CH3CH2C(triple bond)CH.

 

[chemisttree]

I'm not sure about that last step. And where did you find that first step? Seems pretty exotic where a much simpler reaction would do.