Z vs E for cycloalkane with one substituent

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Isa AbdulCader 3K
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Joined: Fri Sep 25, 2015 3:00 am

Z vs E for cycloalkane with one substituent

Postby Isa AbdulCader 3K » Sat Mar 12, 2016 9:38 pm

In Winter 2012 Final Exam, on Problem 5 Part II, it asks for the IUPAC name of molecule B, which is Z-cyclooct-4-enone. How is it considered cis- when there is only one substituent? Does the naming just default to Z when there is only one? Side question, what do you name (Z/E) when it is ambiguous (ex, a cyclohexane with two substituents coming straight out of opposite sides)? Many thanks

Cindy Chen_2I
Posts: 43
Joined: Wed Nov 18, 2015 3:00 am

Re: Z vs E for cycloalkane with one substituent

Postby Cindy Chen_2I » Sat Mar 12, 2016 10:47 pm

Here the Z is actually referring to the double bond in the cycloalkene. When the ring gets large enough, such as in this case there are 8 carbons, then the double bond can actually bend inward.
https://en.wikipedia.org/wiki/Cyclooctene

There's a picture on wiki that shows you how it bends.


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