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For the structure below,

enter image description here

if we use trivial name for complex substituent, do we call it
5-butyl-10-sec-butyltetradecane, or
5-sec-butyl-10-butyltetradecane?

Considering that both substituent are placed in a symmetrical way in the parent chain and sec- prefix are not included in alphabetizing, which one is preferred?

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  • $\begingroup$ Note that the prefix sec-butyl was still contained in the 1993 IUPAC recommendations but is no longer recommended in the current (2013) recommendations. $\endgroup$ – Loong Jun 16 '18 at 8:01
  • $\begingroup$ Related: t-butyl VS s-butyl $\endgroup$ – Loong Jun 16 '18 at 8:10
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This may be resolved by IUPAC Rule A-2.3(ii) which says "The name of a complex radical is considered to begin with the first letter of its complete name," which seems to suggest to me "sec-butyl" is considered to start with "s" and not "b" in this case. As I interpret Rule A-2.3(i) it is only multiplying prefixes (di-, tri-) which are ignored when alphabetizing substituent names.

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  • $\begingroup$ but as far as i understand, sec, tert prefixes are not used for alphabetizing as well as the multiplying prefixes. only iso prefix is included in alphabetizing. pls correct me if i am wrong. $\endgroup$ – Tika Jun 20 '18 at 10:13
  • $\begingroup$ this problem wont occur if we change the sec-butyl to 1-metylpropyl, thus the name will become 5-butyl-10-(1-metylpropyl)tetradecane $\endgroup$ – Tika Jun 20 '18 at 10:15

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