3-propyl-penta-1,3-diene vs 3-ethylidene-hex-1-ene

Asked Feb 22 '21 at 16:13

Active Feb 28 '21 at 16:48

Viewed 252 times

From the rules I know I would name the following compound as 3-propyl-penta-1,3-diene because maximum number of functional groups (double bonds in this case) are in the five numbered carbon chain:

However, ChemDraw names the above compound as 3-ethylidene-hex-1-ene. Why? Am I missing a rule?

edited Feb 28 '21 at 16:48

asked Feb 22 '21 at 16:13

V.G

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This compound also has stereochemistry ($E/Z$). – Mathew Mahindaratne Feb 22 '21 at 16:29
If we ignore E/Z nomenclature at the moment @Mathew Mahindaratne , what about the main name? – V.G Feb 22 '21 at 16:31
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Naming rules include identifying the longest carbon chain. – z1273 Feb 22 '21 at 16:49
I know that, but there is another rule that if there are functional groups present, we choose the longest chain which has maximum number of functional groups, and since it contains two double bonds IMO 5 numbered chain should be considered as parent chain. Can I get a reference? @z1273 – V.G Feb 22 '21 at 16:58
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Related: How do you name an alkene using IUPAC rules if the longest carbon chain in this alkene does not include the double bond? – Loong Feb 22 '21 at 17:19
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@Loong Can you provide a source from where I can refer nomencluature rules, I don't have access to the blue book. – V.G Feb 28 '21 at 10:15
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@LightYagami Start here: Brief guide to the nomenclature of organic chemistry (IUPAC Technical Report) 2020 – Loong Feb 28 '21 at 10:21

3-propyl-penta-1,3-diene vs 3-ethylidene-hex-1-ene

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