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Intext Questions · 7.3

Q.Name the following compounds according to IUPAC system.

(i) CH3−CH2−CH∣CH2Cl−CH∣CH2OH−CH∣CH3−CH3\mathrm{CH_3-CH_2-\underset{\underset{\displaystyle CH_2Cl}{|}}{CH}-\overset{\overset{\displaystyle CH_2OH}{|}}{CH}-\underset{\underset{\displaystyle CH_3}{|}}{CH}-CH_3}
(ii) CH3−CH∣CH3−CH2−CH∣OH−CH∣CH2OH−CH3\mathrm{CH_3-\underset{\underset{\displaystyle CH_3}{|}}{CH}-CH_2-\underset{\underset{\displaystyle OH}{|}}{CH}-\overset{\overset{\displaystyle CH_2OH}{|}}{CH}-CH_3}
Intext 7.3 (iii): structure(s) drawn as printed in the NCERT textbook, with the labels OH, Br
Figure
(iv) H2C=CH−CH∣OH−CH2−CH2−CH3\mathrm{H_2C=CH-\underset{\underset{\displaystyle OH}{|}}{CH}-CH_2-CH_2-CH_3}
(v) CH3−C∣CH3=C∣Br−CH2OH\mathrm{CH_3-\underset{\underset{\displaystyle CH_3}{|}}{C}=\underset{\underset{\displaystyle Br}{|}}{C}-CH_2OH}
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These are polyfunctional alcohols; in each, the -OH (or the pair of -OH groups, for a diol) fixes the parent and gets the lowest locant, and the halogen/alkyl/double-bond are prefixes or the '-en-' infix.

Concept

The hydroxyl group is senior, so the parent chain must contain the carbinol carbon(s) and -OH receives the lowest possible number. A double bond is shown by 'en' with its own locant; halogens and alkyl groups are alphabetised prefixes.

Step-by-step

  1. The carbinol carbon (-CH2OH) is C-1. Taking the four-carbon chain -CH2OH-CH-CH-CH2Cl as the parent (butan-1-ol) gives an isopropyl [1-methylethyl] group at C-2, an ethyl at C-3 and chlorine at C-4, so it is 4-chloro-3-ethyl-2-(1-methylethyl)butan-1-ol. (This is the name expected by NCERT/CBSE; note that by the strict longest-chain rule the same molecule can also be written as 3-(chloromethyl)-2-(1-methylethyl)pentan-1-ol.)
  2. Both -OH groups (one -OH and one -CH2OH) lie on a six-carbon chain, giving hexane-1,3-diol, with methyls at C-2 and C-5, so it is 2,5-dimethylhexane-1,3-diol. …

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