r/chemhelp • u/Suspicious_Isopod403 • 2d ago

General/High School organic chemistry help

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guys i’m so confused how does 2-pentyl butanoate make sense. I have no idea how to draw it bc i thought we didn’t have to number esters. I would appreciate any help, i’m in a grade 12U class

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u/shedmow Trusted Contributor 2d ago

Pentane is the parent chain
-yl indicates that something's cooking (the chain gets a radical, anion, cation, or substituted)
2 shows where

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u/Suspicious_Isopod403 2d ago

is this a more advanced topic higher then hs? All i know is my teacher said that -yl is for the branches

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u/shedmow Trusted Contributor 2d ago edited 2d ago

Speaking from my experience, we were explained/shown basic radical reactions (halogenation, Kharasch) and taught how to convert alkanes into substituents (remove -ane add -n-yl or just -yl for n=1), anions and cations have never been mentioned. The proper IUPAC nomenclature is alkyl for R· and R—somethingelse, alkylium for R+, alkylide for R-, but the last two are also very commonly called alkyl cations and anions

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u/shedmow Trusted Contributor 2d ago

Maybe that will explain the logic

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u/ZevKyogre 2d ago

I would not show it as a cation. 2-pentanol + butanoic acid will form the ester, is the simplest explanation.

You can turn an aldehyde to a carboxylic acid very easily.

You can create 2-pentanol from the alkene (n-pentene I assume) by a standard reaction.

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u/shedmow Trusted Contributor 2d ago

This was meant to show the way by which names of esters and salts are related and not tell that this is the main (or only) method of their synthesis. This conception used to go so deep that alkyl halides (!) were treated as esters (esters as a broader category, not exclusively carboxylic) by at least some, and they are completely isolated in the contemporary common consciousness. I'm not likely to find that book so you have to trust my word for it. How the aldehyde oxidation is related to ester formation (here specifically)?