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Chapter 7: Q12P-b (page 197)

Rank the substituents in each of the following sets according to the sequence rules:

-CH3,-CH2CH3,-CH=CH2,CH2OH

Short Answer

Expert verified

Higher to lower-ranking:-CH2OH>-CH=CH2>-CH2CH3>-CH3

Step by step solution

01

E and Z designation

Cis-trans naming is limited to alkenes with two substituents other than hydrogen on the double bond. But when trisubstituted and tetrasubstituted of the double bond is present then the E and Z system is used for describing alkene stereochemistry.

02

Rule for ranking substituents

  • Consider each of the double-bond carbons separately and ranks the two substituents according to the atomic number of the first atom in each. An atom with a higher atomic number will rank higher.
  • If the first atom same then, look at the second, third, or fourth atoms away from the double-bond until the first difference is found.
  • Multiple-bonded atoms are equivalent to the same number of single-bonded atoms.
03

Ranking of given groups

As ranking is atomic number dependent, more the atomic number higher will be ranking. So,

  • In-CH2OH carbon is attached to two hydrogens and one oxygen.
  • In-CH=CH2 carbon is attached to two carbon and one hydrogen.
  • In -CH2CH3carbon is attached to two hydrogens and one carbon.
  • In -CH3carbon is attached to three hydrogens only.
  • So, higher to lower-ranking:-CH2OH>-CH=CH2>-CH2CH3>-CH3

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