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Topic: O-Chem help: what is iso  (Read 3027 times)

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Offline Foobarz

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O-Chem help: what is iso
« on: April 03, 2012, 10:17:40 PM »
What do the prefixes iso, sec, and tert mean?

Offline XGen

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Re: O-Chem help: what is iso
« Reply #1 on: April 03, 2012, 11:54:22 PM »
These are used in naming the isomers of alkanes.

Offline fledarmus

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Re: O-Chem help: what is iso
« Reply #2 on: April 04, 2012, 08:37:08 AM »
Before IUPAC nomenclature, in the old system of alkane and alcohol nomenclature, the straight chain alkane was called the n-alkane, or normal alkane. For example, n-butyl alcohol would now be called 1-butanol, and n-butane would simply be called butane. sec meant secondary, which for an alcohol meant the OH was a secondary alcohol, and for an alkane meant that one methyl group had been moved to a secondary position - so sec-butyl alcohol would now be called 2-butanol and sec-butane would be called 2-methylpropane. tert meant tertiary, so the alcohol was on a tertiary carbon - tert-butyl alcohol or t-butyl alcohol l would now be called 2-methyl-2-propanol.

Iso was sort of a catch-all - it was the "other isomer". It came to mean an isomer that add a dimethyl methine at one end, like an isopropyl group. So 2-propanol was more commonly called isopropyl alcohol than sec-propyl alcohol. Isobutyl alcohol was the alcohol that wasn't n-, sec-, or tert-butyl alcohol, which would now be called 2-methyl-1-propanol. Isoamyl alcohol was the five carbon analog, 3-methyl-1-butanol.

Neo was also used, being the isomer with a t-butyl group at one end. Neopentyl alcohol was the smallest of these, 2,2-dimethyl-1-propanol. The system of common names quickly got clunky and required a lot of memory work as more carbons were added, which is one reason we have an IUPAC system of systematic nomenclature now.

You can see the common names for the 5-carbon alcohols here, which will give you some idea of the problems involved:

http://en.wikipedia.org/wiki/Amyl_alcohol


Offline Foobarz

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Re: O-Chem help: what is iso
« Reply #3 on: April 14, 2012, 02:41:05 PM »
Oh my the iso and neo are still a little bit confusing, could you please clarify their definitions?

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