EBK ESSENTIAL ORGANIC CHEMISTRY
3rd Edition
ISBN: 8220100659461
Author: 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?
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?
9.a. Circle all the appropriate terms.
t-Bu
The two molecules drawn above are
enantiomers
optically active
enantiomers
superimposable
9.b. Circle all the appropriate terms.
diastereomers
not optically active
H
optically active
Bull....
H₂CH...
Br
-CH3
The two molecules drawn above are
Me
H
diastereomers
not optically active
superimposable
Me
chiral
meso
not superimposable
H3C-
H
.......
chiral
meso
H
...III\CH3
Br
not superimposable
Cl
achiral
-t-Bu
identical
achiral
identical
3
Chapter 4 Solutions
EBK ESSENTIAL ORGANIC CHEMISTRY
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_forwardConsider the following six compounds (A–F). How are the two compounds in each pair related? Choose from enantiomers, epimers, diastereomers but not epimers, constitutional isomers, and identical compounds.a. A and Bb. A and Cc. B and Cd. A and De. E and Farrow_forward
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