Self Test 1.5B

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Natalie Yakobian
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Joined: Fri Sep 25, 2015 3:00 am

Self Test 1.5B

Postby Natalie Yakobian » Thu Feb 25, 2016 11:19 pm

Hi I was wondering if anyone understood what the question from Self Test 1.5B was asking for. It asks us to identify 2-methyl-1,3-butadiene but I don't see any possible structure for that in Limonene. Each molecule seems to only have 1 single bond. What am I doing wrong?

Thanks so much!

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Re: Self Test 1.5B

Postby Chem_Mod » Fri Feb 26, 2016 1:01 am

This question is slightly misleading but the concept is extremely important in nature.

2-methyl-1,3-butadiene is also known as isoprene. It is a 5 carbon unit. Tons and tons of natural molecules are structurally composed of, and biologically synthesized from, isoprene building blocks. Limonene is one example of such.

Limonene has 10 carbons so you automatically know it contains 2 isoprene units. The trick is that when isoprene units come together to build bigger things, there is rearrangement of which bonds are single/double. So all you have to do is find the two isoprene SHAPES in limonene, do not have to worry about single/double bonds.

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