Concept explainers
(a)
Interpretation: The stereogenic centers in the ball-and-stick model of ezetimibe are to be located.
Concept introduction: A carbon atom that has four nonequivalent atoms or groups attached to it is known as chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers.
Answer to Problem 39P
The stereogenic centers in ezetimibe are,
Explanation of Solution
The given ball-and-stick model of ezetimibe is shown below.
Figure 1
In the ball-and-stick model of ezetimibe, yellow balls represent halogen atom as they contain one covalent bond. Black balls are bonded to each other through four covalent bonds, thus; they represent carbon atom. Red balls represent oxygen atom as they contain two covalent bonds and blue balls represent nitrogen atom because they contain three covalent bonds.
The stereogenic center is one that has four different groups attached to carbon atom tetrahedrally. The stereogenic centers in the given molecule are located by omitting all
Figure 2
There are three stereogenic centers present in ezetimibe.
There are three stereogenic centers present in ezetimibe.
(b)
Interpretation: Each stereogenic center in ezetimibe are to be labeled as
Concept introduction: A carbon atom that has four nonequivalent atoms or groups attached to it is known as chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers.
The naming of chiral center and geometric isomers are based on Cahn-Ingold-Prelog priority rules. If the priority assigned to each group attached to the chirality center in a molecule is in a clockwise direction, then it is the R-stereoisomer, and if this is counter-clockwise, then it is the S-stereoisomer. R and S-stereoisomer are mirror images of each other.
Answer to Problem 39P
The
Explanation of Solution
The
Figure 3
The stereogenic center (1) has
In ezetimibe, one of the stereogenic centers has
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Chapter 5 Solutions
ORGANIC CHEMISTRY (LOOSELEAF)
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