Concept explainers
(a)
Interpretation: The structure of naturally occurring
Concept introduction: A compound exhibits number of stereoisomers when it contains more than one stereogenic centers. The maximum number of stereoisomers a compound with
Answer to Problem 5.55P
The structure of naturally occurring
Explanation of Solution
The structure of given compoundis shown below.
Figure 1
The stereochemistry of the compound is determined by prioritizing the groups attached to its stereogenic center. The groups are prioritizedon the basis ofatomic number of their atoms. The group that contains atom with a the higher
The configuration at the first stereocenter of
Figure 2
The above structure implies that the configuration at the first stereocenter of
The configuration at the second stereocenter of
Figure 3
The above structure implies that the configuration at the second stereocenter of
The configuration at both the stereocenters of
Figure 4
The configurations at the first and second stereocenters of
The structure of naturally occurring
(b)
Interpretation: The structure of naturally occurring
Concept introduction: A compound exhibits number of stereoisomers when it contains more than one stereogenic centers. The maximum number of stereoisomers a compound with
Answer to Problem 5.55P
The structure of naturally occurring
Explanation of Solution
The structure of naturally occurring
Figure 5
The stereochemistry of the compound is determined by prioritizing the groups attached to its stereogenic center. The groups are prioritizedon the basis of atomic number of their atoms. The group that contain atom with higher atomic number is givenhigher priority. Complete the circle in decreasing order of priorityfrom
The configuration at first chiral center of
Figure 6
The above structure implies that the configuration at the first stereocenter of
The configuration at the second chiral center of
Figure 7
The above structure implies that the configuration at the second stereocenter of
The configuration at the first and second chiral centers of
Figure 8
The configurations at the first and second carbon atoms of
The structure of naturally occurring
(c)
Interpretation: The relationship between ephedrine and pseudoephedrine is to be identified.
Concept introduction: A compound exhibits number of stereoisomers when it contains more than one stereogenic centers. The maximum number of stereoisomers a compound with
Answer to Problem 5.55P
Ephedrine and pseudoephedrine are related as diastereomers.
Explanation of Solution
The relationship between ephedrine and pseudoephedrine is shown below.
Figure 9
One stereocenter in both the compounds has opposite configuration, while the other stereogenic center has the same configuration. Therefore, both the compounds are related as diastereomer.
Ephedrine and pseudoephedrine are related as diastereomers.
(d)
Interpretation: All the stereoisomers of
Concept introduction: A compound exhibits number of stereoisomers when it contains more than one stereogenic centers. The maximum number of stereoisomers a compound with
Answer to Problem 5.55P
The stereoisomers of
Explanation of Solution
The stereoisomers of
Figure 10
Both the stereoisomers have two stereocenters. One stereocenter in both the compounds has the same configuration, while the other stereocenter in both the compounds has opposite configuration.
The stereoisomers of
(e)
Interpretation: The relationship between each compound drawn in part (d) and
Concept introduction: A compound exhibits number of stereoisomers when it contains more than one stereogenic centers. The maximum number of stereoisomers a compound with
Answer to Problem 5.55P
The relationship between each compound drawn in part (d) and
Explanation of Solution
The relationship between each compound drawn in part (d) and
Figure 11
The compounds
The relationship between each compound drawn in part (d) and
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Chapter 5 Solutions
Organic Chemistry
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- 1 Provide the IUPAC name of the following compounds, with clear indication of stereochemistry for stereocenters and alkene. (a) (b) Br (c) Me. (d) Mearrow_forward1. (a) Describe aromaticity, Kekule structure and resonance structure for benzene. (b) Why is benzene more stable than aliphatic alkenes?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning