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What should be its IUPAC name

How many carbon atoms will be there in the parent carbon chain? I have proposed its few names, which one is more appropriate?

  1. 4-Chloro-3-ethyl-2-(1-methylethyl)-butan-1-ol
  2. 3-(1-Chloromethyl)-2-(1-methylethyl)-pentan-1-ol

Although the answer given in my book is option (1), I have a little confusion regarding why option (2) is incorrect. Since we know that halogens are treated as substituents(suffixes are never used for them), not functional groups in nomenclature, shouldn't number of carbons be given more priority than substituents like Cl? Then, in that case, option (2) must be the right answer. Could anyone who is familiar with latest IUPAC rules enlighten me regarding this? And if you think of any more possibilities of naming this compound other than these two, please share it with me.

This question has already been asked on Quora, but I couldn't find any of the answers satisfactory as some of them choose 5 carbons in PCC, some 4 and some even 6, which made me even more confused.(https://qr.ae/prlmhm)

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    $\begingroup$ Looks to me like your textbook is wrong: there are six carbons in the primary chain. Tell us which textbook so we can warn others about it. $\endgroup$
    – matt_black
    Mar 22, 2023 at 9:51
  • $\begingroup$ NCERT book std 12. I doubt it is available outside India also, so no need to be worried about. Fun fact: It is considered the most standard book in India that even wrong things are considered to be true if it is mentioned in the book. $\endgroup$
    – Dheeraj
    Mar 22, 2023 at 10:18
  • $\begingroup$ Possibly of relevance: v.cx/2010/04/feynman-brazil-education $\endgroup$
    – matt_black
    Mar 22, 2023 at 10:31
  • $\begingroup$ @matt_black You are right that the textbook is wrong; however, there are five carbons in the primary chain. $\endgroup$
    – Loong
    Mar 22, 2023 at 18:17
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    $\begingroup$ @matt_black See my answer. When selecting the parent chain, the suffix ("-ol") comes before the longest chain. $\endgroup$
    – Loong
    Mar 24, 2023 at 15:57

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