Concept explainers
Convert each compound to a Fischer projection and label each stereogenic center as
a. c. e.
b. d. f.
(a)
Interpretation: The given compound is to be converted into Fischer projection and the stereogenic center of a compound is to be labeled as
Concept introduction: In Fischer projection formula, the horizontal and vertical line represents the bonds that are present above and below the plane, respectively. The verticals bonds are represented as dashed wedge and horizontal bonds as dark wedge.
Answer to Problem 28.40P
The Fischer projection of given compound is,
The stereogenic center of a compound is labeled as
Explanation of Solution
The structure of given compound is,
Figure 1
The horizontal and vertical line represents the bonds in front of the plane and behind the plane. Hence, the Fischer projection of given compound is shown below.
Figure 2
In the compound,
Figure 3
The circle rotates in the anticlockwise direction. Thus, the given compound is labeled as
Hence, the Fischer projection of given compound is shown in Figure 2 and the stereogenic center of a compound is labeled as
The Fischer projection of given compound is shown in Figure 2 and the stereogenic center of a compound is labeled as
(b)
Interpretation: The given compound is to be converted into Fischer projection and the stereogenic center is to be labeled as
Concept introduction: In Fischer projection formula, the horizontal and vertical line represents the bonds that are present above and below the plane, respectively. The verticals bonds are represented as dashed wedge and horizontal bonds as dark wedge.
Answer to Problem 28.40P
The Fischer projection of given compound is,
The stereogenic center of a compound is labeled as
Explanation of Solution
The structure of given compound is,
Figure 4
The given compound is redrawn. The horizontal and vertical line represents the bonds in front of the plane and behind the plane is shown below.
Figure 5
Hence, the Fischer projection of given compound is shown below.
Figure 6
In the compound,
Similarly, the third and forth priorities are given to
Figure 7
The circle rotates in the anticlockwise direction. Thus, the given compound is labeled as
Hence, the Fischer projection of given compound is shown in Figure 6 and the stereogenic center of a compound is labeled as
The Fischer projection of given compound is shown in Figure 6 and the stereogenic center of a compound is labeled as
(c)
Interpretation: The given compound is to be converted into Fischer projection and the stereogenic center is to be labeled as
Concept introduction: In Fischer projection formula, the horizontal and vertical line represents the bonds that are present above and below the plane, respectively. The verticals bonds are represented as dashed wedge and horizontal bonds as dark wedge.
Answer to Problem 28.40P
The Fischer projection of given compound is,
The stereogenic center of a compound is labeled as
Explanation of Solution
The structure of given compound is,
Figure 8
The given compound is redrawn. The horizontal and vertical line represents the bonds in front of the plane and behind the plane. Hence, the Fischer projection of given compound is shown below.
Figure 9
Hence, the Fischer projection of given compound is shown below.
Figure 10
In the compound,
Figure 11
The circle rotates in the anticlockwise direction. Thus, the given compound is labeled as
Hence, the Fischer projection of given compound is shown in Figure 10 and the stereogenic center of a compound is labeled as
The Fischer projection of given compound is shown in Figure 10 and the stereogenic center of a compound is labeled as
(d)
Interpretation: The given compound is to be converted into Fischer projection and the stereogenic center is to be labeled as
Concept introduction: In Fischer projection formula, the horizontal and vertical line represents the bonds that are present above and below the plane, respectively. The verticals bonds are represented as dashed wedge and horizontal bonds as dark wedge.
Answer to Problem 28.40P
The Fischer projection of given compound is,
The stereogenic center of a compound are labeled as
Explanation of Solution
The structure of given compound is,
Figure 12
The horizontal and vertical line represents the bonds in front of the plane and behind the plane. Hence, the Fischer projection of given compound is shown below.
Figure 13
In the compound,
Similarly, in the
Figure 14
Hence, the Fischer projection of given compound is shown in Figure 13 and the stereogenic center of a compound are labeled as
The Fischer projection of given compound is shown in Figure 13 and the stereogenic center of a compound are labeled as
(e)
Interpretation: The given compound is to be converted into Fischer projection and the stereogenic center is to be labeled as
Concept introduction: In Fischer projection formula, the horizontal and vertical line represents the bonds that are present above and below the plane, respectively. The verticals bonds are represented as dashed wedge and horizontal bonds as dark wedge.
Answer to Problem 28.40P
The Fischer projection of given compound is,
The stereogenic center of a compound as
Explanation of Solution
The structure of given compound is,
Figure 15
The given compound is redrawn. The horizontal and vertical line represents the bonds in front of the plane and behind the plane as shown below.
Figure 16
Hence, the Fischer projection of given compound is shown below.
Figure 17
In the compound,
Similarly, in the
Figure 18
Hence, the Fischer projection of given compound is shown in Figure 17 and the stereogenic center of a compound are labeled as
The Fischer projection of given compound is shown in Figure 17 and the stereogenic center of a compound are labeled as
(f)
Interpretation: The given compound is to be converted into Fischer projection and the stereogenic center is to be labeled as
Concept introduction: In Fischer projection formula, the horizontal and vertical line represents the bonds that are present above and below the plane, respectively. The verticals bonds are represented as dashed wedge and horizontal bonds as dark wedge.
Answer to Problem 28.40P
The Fischer projection of given compound is,
The stereogenic center of a compound are labeled as
Explanation of Solution
The structure of given compound is,
Figure 19
The Fischer projection is drawn by converting the stable staggered conformation into less stable eclipsed conformation. The bonds present below the plane in eclipsed conformation are placed on the left side of the horizontal line in Fischer projection formula as shown below.
Figure 20
Hence, the Fischer projection of given compound is shown below.
Figure21
In the compound,
Similarly, in the
Similarly, in the
Figure 22
Hence, the Fischer projection of given compound is shown in Figure 21 and the stereogenic center of a compound are labeled as
The Fischer projection of given compound is shown in Figure 21 and the stereogenic center of a compound are labeled as
Want to see more full solutions like this?
Chapter 28 Solutions
Organic Chemistry
- Problem 5.16 Label each stereogenic center as R or S. Br b. ge, HO н он ca C. t d. OHe o lobonot b d or HOP "OH f. HO Harrow_forwardSaquinavir (trade name Invirase) is a protease inhibitor, used to treat HIV (human immunodeficiency virus). a.Locate all stereogenic centers in saquinavir, and label each stereogenic center as R or S. b.Draw the enantiomer of saquinavir. c.Draw a diastereomer of saquinavir. d.Draw a constitutional isomer that contains at least one different functional group.arrow_forwardLabel each stereogenic center as R or S (Questions a, b and c please)arrow_forward
- Problem 5.2 Classify each pair of compounds as constitutional isomers or stereoisomers. a. and and он 020st geabe AA go Aon e 2o3 С. and d. and b.arrow_forwarda.Label the four stereogenic centers in sorbitol as R or S. b.How are sorbitol and A related? c. How are sorbitol and B related?arrow_forwardProblem 5.20 Label the two stereogenic centers in dB re stereoisomers. ne. each compound and draw all possible CI a. rro OH Br CI ne b. B. Problem 5.21 Compounds E and F are two isomers of 2,3-dibromopentane drawn in staggered conformations. Which compounds (A-D) in Figure 5.8 are identical to E and F? im et wihr boe A mot Br omin oldne Br F Brarrow_forward
- Problem 5.22 Draw all the possible stereoisomers for each compound, and label pairs of enantiomers hen and diastereomers. Ust a. OH fevidas OH b. CIto snelg e vil OHarrow_forward(a) Locate the stereogenic centers in the ball-and-stick model of ezetimibe (trade name Zetia), a cholesterol-lowering drug. (b) Label each stereogenic center as R or S. ezetimibearrow_forwardCaptopril is a drug used to treat high blood pressure and congestiveheart failure.Designate each stereogenic center as R or S.arrow_forward
- Label each stereogenic center as R or S (parts d, e and f please)arrow_forwardProblem 5.24 Draw a meso compound for each of the following molecules. a. Br CI Br b. HO OH c. H₂N NH₂arrow_forwardDesignating a Stereogenic Center as R or S When the Lowest-Priority Group Is Not Drawn Back Label each stereogenic center as Ror S. а. OH b. OHarrow_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