An unknown compound, B, has the molecular formula C7H12. On catalytic hydrogenation 1 mol of B absorbs 2 mol of hydrogen and yields 2-methylhexane. B has significant IR absorption band at about 3300 and 2200 cm-1. Which compound best represents B?

5-methylhex-1-yne//5-methylhex-2-yne//2-methylhex-3-yne

Explanation:

We have to start with the information on the IR spectrum. The signal at 3300 is due to a C-H bend sp carbon and the signal in 2200 is due to the stretch carbon-carbon. Therefore we will have an alkyne. Now if we have 2-methylhexane as the product of hydrogenation we have several options to put the triple bond. 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!

1. they vary with a higher number because boiling is way hotter than melting

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