Final answer:
Treating 4,5,5-trimethyl-1-hexyne with two equivalents of HBr leads to the formation of 4,5,5-trimethyl-2,3-dibromohexane. The reaction involves Markovnikov's addition of HBr to the alkyne, first yielding an alkene, and then another HBr addition to form the dibrominated alkane.
Step-by-step explanation:
Hydrobromination of 4,5,5-Trimethyl-1-hexyne
When 4,5,5-trimethyl-1-hexyne, which is a terminal alkyne, is treated with two equivalents of HBr, the reaction follows Markovnikov's rule resulting in the addition of hydrogen and bromine atoms across the triple bond. The alkyne first undergoes hydrobromination to become an alkene, and then the alkene undergoes a second hydrobromination to form the final alkane. The outcome is a fully saturated hydrocarbon.
The process is stepwise, with the alkene intermediate not usually isolated. In the initial step, the addition of one equivalent of HBr would yield 4,5,5-trimethyl-2-bromohexene as the alkene. The second addition of HBr breaks the double bond and adds another bromine to the more substituted carbon due to Markovnikov's rule. This gives us a dibrominated alkane as the final product. Taking into account the structure of 4,5,5-trimethyl-1-hexyne, where there are three methyl groups on the 4th and 5th carbons, the final product after two equivalents of HBr have reacted will be 4,5,5-trimethyl-2,3-dibromohexane.
However, referring to the provided reference, it appears that there might be a typo since the suggested alkanes in the solution, 2-bromopentane, and 4-bromo-2-methylhexane do not correspond to the original compound 4,5,5-trimethyl-1-hexyne. Thus, these names are likely errors and are not the answer to the reaction in question.