internal alkyne stability to strong alkali

Internal alkynes are relatively electron rich and are not *usually* prone to attack by strong (nucleophilic) bases such as hydroxide or alkoxide.


However, this isn't always the case. A [very nice overview](https://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/addyne1.htm) of the most common reactions of alkynes says:



> 
> The sp-hybrid carbon atoms of the triple-bond render alkynes more electrophilic than similarly substituted alkenes. As a result, alkynes sometimes undergo addition reactions initiated by bonding to a nucleophile. This mode of reaction, illustrated below, is generally not displayed by alkenes, unless the double-bond is activated by electronegative substituents, e.g. $\ce{F2C=CF2}$, or by conjugation with an electron withdrawing group.
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> 
> $\ce{HC≡CH + KOC2H5 —>[in C2H5OH at 150 ºC] H2C=CH-OC2H5}$
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> 


**I'm interested in more information about this and similar reactions, particular for internal (not acetylenic) alkynes.**


Unfortunately, the linked page doesn't provide a reference for this reaction, and searching in Google Scholar for "internal alkyne" "potassium hydroxide" doesn't provide useful results.


Thus my questions are:


1. **Does hydroxide ever react similarly with internal alkynes, at *any* temperature?** If so, under what conditions?
2. How long does the ethoxide reaction indicated above (at 150 °C) take? Days? Hours? Minutes? Would it be significantly different for an internal alkyne rather than acetylene?
3. In the case of a hydroxide reaction, would the ultimate product be a ketone (a.k.a. base catalyzed hydration)?




According to [A Textbook of Organic Chemistry](https://www.google.com/search?tbm=bks&hl=en&q=%22hydroxide%20and%20the%20reverse%20of%20this%20reaction%22&=) by V. K. Ahluwalia and Madhuri Goyal



> 
> 1-Butyne may be isomerised to a more stable 2-butyne in presence of alcoholic potassium hydroxide and the reverse of this reaction may occur with sodamide
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(see 17.2.1 of [Best Synthetic Methods: Acetylenes, Allenes and Cumulenes](https://books.google.com/books?id=jBkCH-v9-j8C&pg=PA320&dq=1-Butyne%20isomerised%20%202-butyne&hl=en&sa=X&ved=0ahUKEwjOvKTr6OTQAhVZVWMKHduABboQ6AEIPjAG#v=onepage&q=1-Butyne%20isomerised%20%202-butyne&f=false) for reaction conditions in the 2-alkyne to 1-alkyne direction, actually many relevant reactions are in this book)


So in the present of the strong base $\ce{NaNH2}$ the internal alkyne $\ce{H3CC#CCH3}$ rearranges to $\ce{HC#CCH2CH3}$


My thinking is that with just hydroxide the more stable 2-butyne is favored, while if an even-stronger base is used, that fact that the acetylenic-H can deprotonate pulls the equilibrium toward 1-butyne. 


Additionally, see [17.2.11](https://books.google.com/books?id=jBkCH-v9-j8C&pg=PA331&dq=%2217.2.11%20isomerisation%20of%22&hl=en&sa=X&ved=0ahUKEwiSwbn-6uTQAhVB7WMKHS3MBLsQ6AEIGjAA#v=onepage&q=%2217.2.11%20isomerisation%20of%22&f=false) Isomerisation of 1,4 bis(alkoxy)-2-butynes to the corresponding allenes, which is catalyzed by t-BuOK.


Add see table 17.1 "Base catalyzed isomerisations of acetylenic compounds" about 10 different internal acetylene reactions are listed in the table. 


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