
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 5.51P
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 5.51P
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 5.51P
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 5.51P
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 5.51P
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-Package(Custom)
- Name the major organic product of the following action of 4-chloro-4-methyl-1-pentanol in neutral pollution 10+ Now the product. The product has a molecular formula f b. In a singly hain, the starting, material again converts into a secule with the molecular kormula CIO. but with comply Draw the major organic structure inhalationarrow_forwardMacmillan Learning Alcohols can be oxidized by chromic acid derivatives. One such reagent is pyridinium chlorochromate, (C,H,NH*)(CICTO3), commonly known as PCC. Draw the proposed (neutral) intermediate and the organic product in the oxidation of 1-butanol by PCC when carried out in an anhydrous solvent such as CH₂C₁₂. PCC Intermediate OH CH2Cl2 Draw the intermediate. Select Draw Templates More с H Cr о Product Draw the product. Erase Select Draw Templates More H о Erasearrow_forwardIf I have 1-bromopropene, to obtain compound A, I have to add NaOH and another compound. Indicate which compound that would be. A C6H5 CH3arrow_forward
- Provide the reagents for the following reactions.arrow_forwardIf I have 1-bromopropene, to obtain compound Z, I have to add two compounds A1 and A2. Indicate which compounds are needed. P(C6H5)3arrow_forwardDraw the major product of this reaction. Ignore inorganic byproducts. Assume that the water side product is continuously removed to drive the reaction toward products. O CH3CH2NH2, TSOH Select to Draw >arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning

