
Concept explainers
Label each stereogenic center as
a. c.
e.
g.
b. d.
f.
h.

(a)
Interpretation: The stereogenic center in the given compound is 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 5.47P
The stereogenic center has
Explanation of Solution
The
(1) Assign numbering to the groups which are bonded to the chiral carbon based on the molecular weight and electronegativity.
(2) If the sequence of the numbering follows clockwise direction, the chiral atom is assigned
(3) If the sequence of the numbering follows anticlockwise direction, the chiral atom is assigned
(4) If the rotation is clock-wise and the least priority group is above the plane, then the configuration is inverted to the obtained configuration from the above CIP rule which means
In the given compound, the increasing order of priority assigned to the groups attached to chiral center is,
Therefore, the groups in the given compound are numbered as shown below.
Figure 1
The rotation in the above compound is in anticlockwise direction. Hence, the stereogenic center has

(b)
Interpretation: The stereogenic center in the given compound is 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 5.47P
The stereogenic center has
Explanation of Solution
In the given compound, the increasing order of priority assigned to the groups attached to chiral center is,
Therefore, the groups in the given compound are numbered as shown below.
Figure 2
The rotation in the above compound is in clockwise direction and the least priority group is above the plane, then the configuration is inverted. Hence, the stereogenic center has

(c)
Interpretation: The stereogenic center in the given compound is 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 5.47P
The stereogenic center has
Explanation of Solution
In the given compound, the increasing order of priority assigned to the groups attached to chiral center is,
Therefore, the groups in the given compound are numbered as shown below.
Figure 3
The rotation in the above compound is in clockwise direction. Hence, the stereogenic center has

(d)
Interpretation: The stereogenic center in the given compound is 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 5.47P
Both the stereogenic centers has
Explanation of Solution
In the given compound, two chiral centers are present.
Therefore, the groups in the given compound are numbered as shown below.
Figure 4
The rotation of first chiral center in the above compound is in clockwise direction and second chiral center shows anticlockwise rotation. In second chiral center, the least priority group is above the plane, and then the configuration is inverted. Hence, both the stereogenic centers has

(e)
Interpretation: The stereogenic center in the given compound is 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 5.47P
The stereogenic center has
Explanation of Solution
The groups in the given compound are numbered as shown below.
Figure 5
The rotation in the above compound is in anticlockwise direction and the least priority group is below the plane. Hence, the stereogenic center has

(f)
Interpretation: The stereogenic center in the given compound is 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 5.47P
Both the stereogenic centers has
Explanation of Solution
In the given compound, two chiral centers are present.
Therefore, the groups in the given compound are numbered as shown below.
Figure 6
The rotation of first chiral center in the above compound is in clockwise direction and second chiral center shows anticlockwise rotation. In first chiral center, the highest priority group is below the plane, and then the configuration is inverted to

(g)
Interpretation: The stereogenic center in the given compound is 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 5.47P
Both the stereogenic centers has
Explanation of Solution
In the given compound, two chiral centers are present.
Therefore, the groups in the given compound are numbered as shown below.
Figure 7
The rotation of first chiral center in the above compound is in clockwise direction and second chiral center shows anticlockwise rotation. In first chiral center, the highest priority group is below the plane, and then the configuration is inverted to

(h)
Interpretation: The stereogenic center in the given compound is 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 5.47P
The configurations of three stereogenic centers are
Explanation of Solution
In the given compound, three chiral centers are present.
Therefore, the groups in the given compound are numbered as shown below.
Figure 8
The rotation of first chiral center in the above compound is in clockwise direction. Thus, it has
(a) The stereogenic center has
(b) The stereogenic center has
(c) The stereogenic center has
(d) Both the stereogenic centers has
(e) Both the stereogenic centers has
(f) Both the stereogenic centers has
(g) Both the stereogenic centers has
(h) The configurations of three stereogenic centers are
Want to see more full solutions like this?
Chapter 5 Solutions
Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
Additional Science Textbook Solutions
Biology: Life on Earth with Physiology (11th Edition)
Organic Chemistry
Applications and Investigations in Earth Science (9th Edition)
Anatomy & Physiology (6th Edition)
Principles of Anatomy and Physiology
- Synthesize 2-Ethyl-3-methyloxirane from dimethyl(propyl)sulfonium iodide using the necessary organic or inorganic reagents. Draw the structures of the compounds.arrow_forwardSynthesize 2-Hydroxy-2-phenylacetonitrile from phenylmethanol using the necessary organic or inorganic reagents. Draw the structures of the compounds.arrow_forwardSynthesize N-Methylcyclohexylamine from cyclohexanol using the necessary organic or inorganic reagents. Draw the structures of the compounds.arrow_forward
- Synthesize N-Methylcyclohexylamine from cyclohexanol using the necessary organic or inorganic reagents. Draw the structures of the compounds.arrow_forwardIf possible, please provide the formula of the compound 3,3-dimethylbut-2-enal.arrow_forwardSynthesize 1,4-dibromobenzene from acetanilide (N-phenylacetamide) using the necessary organic or inorganic reagents. Draw the structures of the compounds.arrow_forward
- Indicate the products obtained by mixing (3-oxo-3-phenylpropyl)triphenylphosphonium bromide with sodium hydride.arrow_forwardWe mix N-ethyl-2-hexanamine with excess methyl iodide and followed by heating with aqueous Ag2O. Indicate the major products obtained.arrow_forwardIndicate the products obtained by mixing acetophenone with iodine and NaOH.arrow_forward
- Indicate the products obtained by mixing 2-Propanone and ethyllithium and performing a subsequent acid hydrolysis.arrow_forwardIndicate the products obtained if (E)-2-butenal and 3-oxo-butanenitrile are mixed with sodium ethoxide in ethanol.arrow_forwardQuestion 3 (4 points), Draw a full arrow-pushing mechanism for the following reaction Please draw all structures clearly. Note that this intramolecular cyclization is analogous to the mechanism for halohydrin formation. COH Br + HBr Brarrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY





