The alkyne shown is treated with a hindered borane, then $H X_{2} O X_{2}$ / $NaOH$ , and the product is then oxidised with Tollens' reagent. Which structure is the final organic product (after acidification)?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: C

The compound shown is 3,3-dimethylbut-1-yne. Hydroboration-oxidation gives the aldehyde 3,3-dimethylbutanal, which Tollens' reagent oxidises to the acid 3,3-dimethylbutanoic acid. Pivalic acid has one carbon less, the ketone would come from mercury hydration, and the alcohol is not formed.

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The alkyne shown is treated with a hindered borane, then HX2​OX2​/NaOH, and the product is then oxidised with Tollens' reagent. Which structure is the final organic product (after acidification)?

Answer: C

More questions on Alkyne hydration, hydroboration and Diels-Alder products

The alkyne shown is treated with a hindered borane, then $H X_{2} O X_{2}$ / $NaOH$ , and the product is then oxidised with Tollens' reagent. Which structure is the final organic product (after acidification)?