Question

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?

a. 5-methyl-1,3-hexadiene
b. 5-methyl-1-hexyne
c. 3-methyl-1-hexyne
d. 5-methyl-2-hexyne
e. 2-methyl-1,5-hexadiene

Answer 1

B and D

Step-by-step explanation:

If we use the info given we have a band a 3300 cm-1 and 2200 cm-1 this indicates that we have an alkyne functional group. Additionally, the hydrogenation of the unknown molecule will consume two moles of hydrogens this fits with the 2 pi bonds in the alkyne functional group. So, we can discard "a" and "e". The product of this hydrogenation is 2-methylhexane therefore we can discard c because the methyl group is placed on carbon 3. Structures b and d can work.

See figure 1

I hope it helps!