Pearson eText for Essential Organic Chemistry -- Instant Access (Pearson+)
3rd Edition
ISBN: 9780137533268
Author: Paula Bruice
Publisher: PEARSON+
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Question
Chapter 4, Problem 67P
(a)
Interpretation Introduction
Interpretation:
The number of stereoisomers present in given structure of ephedrine has to be determined.
Concept introduction:
Stereoisomers are isomers which have different spatial arrangement in spite of same bond connectivity. Stereoisomers are due to the presence of stereocenter.
Asymmetric center is a stereocenter which arises to hydrocarbons if the carbon is bonded to four different groups.
The equation for finding Stereoisomers from number of asymmetric centers in compounds is
(b)
Interpretation Introduction
Interpretation:
The configuration of each of asymmetric centers has to be given.
Concept introduction:
According to Cahn-Ingold-Prelog system,
The group attached to asymmetric center should be ranked based on the
Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the compound has R configuration. If the arrow points counterclockwise direction, then the compound has S configuration. If the group with lowest priority is not bonded by a hatched wedge, then interchange this group (lowest priority) by group bonded to hatched wedge and draw the arrow in priority order but the configuration is assigned as just reverse.
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Students have asked these similar questions
The stereoisomer of cholesterol found in nature is shown here.a. How many asymmetric centers does cholesterol have? b. What is the maximum number of stereoisomers that cholesterol can have?
For many centuries, the Chinese have used extracts from a group of herbs known as ephedra to treat asthma. A compound named ephedrine has been isolated from these herbs and found to be a potent dilator of air passages in the lungs. a. How many stereoisomers does ephedrine have? b. The stereoisomer shown here is the one that is pharmacologically active. What is the configuration of each of the asymmetric centers?
Which of the two molecules below has more stereoisomers?
O
O
I
O
Br
B. I, because II is a meso compound
C. because it has more chiral centers
O D. II, because I has no enantiomer
A. They have the same number of stereoisomers
Br
E. II, because I is a meso compound
II
Br
S
Chapter 4 Solutions
Pearson eText for Essential Organic Chemistry -- Instant Access (Pearson+)
Ch. 4.1 - Draw the cis and trans isomers for the following:...Ch. 4.1 - Prob. 4PCh. 4.1 - Prob. 5PCh. 4.1 - Prob. 6PCh. 4.2 - Prob. 7PCh. 4.2 - Tamoxifen slows the growth of some breast tumors...Ch. 4.2 - Draw and label the E and Z isomers for each of the...Ch. 4.2 - Prob. 10PCh. 4.2 - Name each of the following:Ch. 4.2 - Draw the structure of (Z)-2,3-dimethyl-3-heptene.
Ch. 4.3 - Prob. 13PCh. 4.4 - Prob. 14PCh. 4.5 - Prob. 16PCh. 4.6 - Prob. 17PCh. 4.7 - Assign relative priorities to the groups or atoms...Ch. 4.7 - Name the following:Ch. 4.7 - Prob. 22PCh. 4.7 - Draw a perspective formula for each of the...Ch. 4.8 - Prob. 24PCh. 4.8 - Prob. 27PCh. 4.9 - Prob. 28PCh. 4.9 - Prob. 29PCh. 4.9 - Prob. 30PCh. 4.10 - Prob. 31PCh. 4.10 - Prob. 32PCh. 4.10 - Prob. 33PCh. 4.11 - Prob. 34PCh. 4.11 - a. Draw the stereoisomers of...Ch. 4.11 - Prob. 37PCh. 4.11 - Prob. 38PCh. 4.12 - Which of the following compounds has a...Ch. 4.12 - Draw all the stereoisomers for each of the...Ch. 4.12 - Limonene exists as two different stereoisomers....Ch. 4 - a. Draw three constitutional isomers with...Ch. 4 - Which of the following have an asymmetric center?...Ch. 4 - Prob. 45PCh. 4 - Prob. 46PCh. 4 - Of all the possible cyclooctanes that have one...Ch. 4 - Prob. 48PCh. 4 - Prob. 49PCh. 4 - Prob. 50PCh. 4 - Prob. 51PCh. 4 - Prob. 52PCh. 4 - Draw the stereoisomers of 2,4-dichlorohexane....Ch. 4 - Prob. 54PCh. 4 - Prob. 55PCh. 4 - Prob. 56PCh. 4 - Prob. 57PCh. 4 - Prob. 58PCh. 4 - Prob. 59PCh. 4 - Prob. 60PCh. 4 - Prob. 61PCh. 4 - Prob. 62PCh. 4 - Draw structures for each of the following: a....Ch. 4 - Prob. 64PCh. 4 - a. Draw all the isomers with molecular formula...Ch. 4 - Prob. 66PCh. 4 - Prob. 67PCh. 4 - Prob. 68PCh. 4 - Chloramphenicol is a broad-spectrum antibiotic...
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- Ephedrine, a stimulant and illegal drug is an optically active compound with two chiral centers. OH NHCH3 CH3 Ephedrine a. In the structure of ephedrine on the answer sheet, mark each chiral center with an asterisk. b. How many stereoisomer/s does ephedrine have? Show necessary solutions on the answer sheet. c. Compound EPS is a stereoisomer of ephedrine. Determine the absolute configuration (R or S) at carbons A and B of compound EPS.arrow_forward17. Enantiomers of CHBrIF Perspective drawings of both enantiomers: a. Make models of both enantiomers (make one model then make its mirror image.) b. Can the two models be superimposed? c. What type of isomerism do these models represent? 18. Geometric Isomers of CICH = CHCI (1,2-dichloroethene) Perspective drawings of both isomers: a. Make two models that have different spatial arrangement of the substitutions (the two Cl atoms) across the double bond. b. Draw the perspective formulae for the two isomers and label them with their correct designations. c. What type of isomerism do these represent?arrow_forwardVIII. Assign R, S configurations to each chirality center in the molecule below. Br CH3 X OH CH3 I I (arrow_forward
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