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Answer:
5-methylhex-1-yne//5-methylhex-2-yne//2-methylhex-3-yne
Explanation:
We have to start with the information on the <u>IR spectrum</u>. The signal at 3300 is due to a <u>C-H bend sp carbon</u> and the signal in 2200 is due to the <u>stretch carbon-carbon</u>. Therefore we will have an alkyne. Now if we have 2-methylhexane as the product of hydrogenation we have <u>several options to put the triple bond</u>. Between carbons 1 and 2 (5-methylhex-1-yne), between carbons 2 and 3 (5-methylhex-2-yne) and between carbons 3 and 4 (2-methylhex-3-yne). On carbon 5 we have a tertiary carbon therefore we dont have any other options.
See figure 1
I hope it helps!
