Which group in each pair is assigned the higher priority in R,S nomenclature?

  1. -CD3,-CH3
  2. localid="1648446360910" -CH(CH3)2,-CH2OH
  3. localid="1648447310055" -CH2Cl,-CH2CH2CH2Br
  4. -CH2NH2,-NHCH3

Short Answer

Expert verified

The following group among the pairs will get the higher priority:

  1. -CD3
  2. -CH2OH
  3. -CH2Cl
  4. -NHCH3

Step by step solution

01

Assigning the R and S nomenclature

The enantiomers of a compound are two separate compounds. According to the rules of IUPAC, the enantiomers are named by adding the prefixes R or S to their IUPAC names.

The priority is assigned to each group that is connected to the stereogenic center. With the help of these priorities, the enantiomers are labeled as R or S.

02

Rules to assign priority

The priority is assigned to various groups based on the following rules:

  • The directly bonded atom, which has the highest atomic number, gets the highest priority.
  • The isotopes with the highest mass number get the highest priority.
  • The multiple bonds are considered as the equal number of singly bonded atoms.
  • If the atoms bonded to the stereocenter are the same, the next bonded atom is considered for assigning priority.
03

Assigning priority to the given group of atoms

For the R and S nomenclature, the priority is assigned in the following way:

a.-CD3,-CH3-CD3,-CH3

Among the above pair, the group -CD3is given the higher priority. Both these groups will be bonded to the stereogenic center by the carbon atom. After the carbon atom, the next atom is considered to assign the priority.

The next atom after the carbon is deuterium in the first group and hydrogen in the second group. Since deuterium has the highest mass number, the -CD3group will get higher priority.

b.-CH(CH3)2,-CH2OH

Among the above pair, -CH2OH will get the higher priority. In this group, the carbon atom is bonded to the oxygen atom.

In -CH(CH3)2 the carbon is bonded to another carbon atom. An oxygen atom has a higher atomic number than carbon; it will get priority over the carbon atom.

c. role="math" localid="1648447325968" -CH2Cl,-CH2CH2CH2Br

Among the above pair, the -CH2Clgroup will get the higher priority. In this group, the carbon atom is bonded to the chlorine atom which has a higher atomic number.

In -CH2CH2CH2Br, the carbon atom is bonded to another carbon atom.

d.-CH2NH2,-NHCH3

Among the above pair, -NHCH3 will get the higher priority because the nitrogen atom has a higher atomic number than the carbon atom.

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