How to Make Use of the Acidic Hydrogen of a Terminal Alkyne in an Organic Synthesis ─ Part 2

Terminal alkynes have the formula RC≡CH, where at least one end of the alkyne is a hydrogen atom, which is acidic since it is connected to an sp-hybridized carbon atom.


A terminal alkyne may be deprotonated by a strong enough base to generate a nucleophile, which can do several reactions like nucleophilic substitutions.

Question:

Predict the major product(s) of the following reaction:



Click/tap to enlarge the image

Solution infographic:



Click/tap to enlarge the image

Disturbed by no deprotonation ❓Let Chemaficionado know in the comments below or at mychemistryhomework@gmail.com❗

References:

(1)    Wikipedia Contributors. Alkyne. Wikipedia. https://en.wikipedia.org/wiki/Alkyne.

‌(2)    Wikipedia Contributors. Nucleophilic substitution. Wikipedia. https://en.wikipedia.org/wiki/Nucleophilic_substitution.‌

(3)    Chouhan, M. S. Advanced Problems in Organic Chemistry for JEE, 11th Ed.

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