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

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To solve the multi-step organic chemistry problem of converting CH3CH2CH2CH2OH to CH3CH2C≡CH, the discussion emphasizes starting with reactions that produce terminal alkynes. A suggested approach involves using BH3 followed by oxidation with H2O2 and HO- to first form an alkene (CH3CH2CH=CH2) before hydrogenating it to yield the desired alkyne. Participants highlight the importance of understanding the reaction mechanisms and suggest simpler alternatives to complex steps. The conversation indicates that the problem may seem daunting initially but can be resolved with the right sequence of reactions. Overall, clarity in reaction pathways is crucial for successfully tackling such organic chemistry challenges.
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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
 
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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.
 
Would it be Hydration-electrophilic addition of water (1. H20, 2. H2SO4 & HgSO4)? If yes, I don't see how.
 
Go the other way first...
 
CH3CH2CH2CH2OH 1.BH3 2. H2O2,HO > CH3CH2CH=CH2 H2 > CH3CH2C(triple bond)CH.
 
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.
 

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