ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
10th Edition
ISBN: 9781259972348
Author: Carey
Publisher: MCG CUSTOM
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 7, Problem 36P
Interpretation Introduction
Interpretation:
The number of stereoisomers possible in Sphingosine are to be determined on the basis of its structure.
Concept introduction:
Stereoisomers have the same molecular formula but a different arrangement of atoms in space.
A carbon atom attached to four different atoms or groups is a chiral carbon atom.
The number of stereoisomers for a particular constitution is
When two atoms or groups of higher priorities are on the same side of the double bond, the double bond has the Z configuration, and when they are on opposite sides, the configuration is E.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Clopidogrel is the generic name for Plavix, a drug used to prevent the formation of blood clots in patients that have a history of heart attacks or strokes. A single enantiomer of clopidogrel can be prepared in three steps from the chiral α-hydroxy acid A. Identify B and C in the following reaction sequence, and designate the configuration of the enantiomer formed by this route as R or S.
The shrub ma huang (Section 5.4A) contains two biologically active stereoisomers—ephedrine and pseudoephedrine—with two stereogenic centers as shown in the given structure. Ephedrine is one component of a once-popular combination drug used by body builders to increase energy and alertness, whereas pseudoephedrine is a nasal decongestant.
a.Draw the structure of naturally occurring (−)-ephedrine, which has the 1R,2S configuration.
b.Draw the structure of naturally occurring (+)-pseudoephedrine, which has the 1S,2S configuration.
c.How are ephedrine and pseudoephedrine related?
d.Draw all other stereoisomers of (−)-ephedrine and (+)pseudoephedrine, and give the R,S designation for all stereogenic centers.
e.How is each compound drawn in part (d) related to (−)-ephedrine?
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?
Chapter 7 Solutions
ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
Ch. 7.1 - Name each of the following using IUPAC...Ch. 7.1 - Prob. 2PCh. 7.2 - How many carbon atoms are sp2-hybridized in the...Ch. 7.3 - Prob. 4PCh. 7.3 - Are cis-2-hexene and trans-3-hexene stereoisomers?...Ch. 7.4 - Prob. 6PCh. 7.4 - Prob. 7PCh. 7.4 - Give the IUPAC name of each of the compounds in...Ch. 7.5 - Arrange the following in order of increasing...Ch. 7.6 - Prob. 10P
Ch. 7.6 - Standard enthalpies of formation are known for all...Ch. 7.6 - Prob. 12PCh. 7.6 - Despite numerous attempts, the alkene...Ch. 7.6 - Write structural formulas for the six isomeric...Ch. 7.7 - Place a double bond in the carbon skeleton shown...Ch. 7.9 - Identify the alkene obtained on dehydration of...Ch. 7.10 - Prob. 17PCh. 7.11 - Prob. 18PCh. 7.12 - Prob. 19PCh. 7.13 - The alkene mixture obtained on dehydration of...Ch. 7.14 - Write the structures of all the alkenes that can...Ch. 7.14 - Write structural formulas for all the alkenes that...Ch. 7.15 - A study of the hydrolysis behavior of...Ch. 7.15 - Use curved arrows to illustrate the electron flow...Ch. 7.15 - Predict the major product of the reaction shown.Ch. 7.16 - Prob. 26PCh. 7.17 - Prob. 27PCh. 7.18 - Prob. 28PCh. 7.19 - Predict the major organic product of each of the...Ch. 7.19 - A standard method for the synthesis of ethers is...Ch. 7 - Write structural formulas for each of the...Ch. 7 - Prob. 32PCh. 7 - Give an IUPAC name for each of the following...Ch. 7 - A hydrocarbon isolated from fish oil and from...Ch. 7 - Prob. 35PCh. 7 - Prob. 36PCh. 7 - Prob. 37PCh. 7 - Prob. 38PCh. 7 - Choose the more stable alkene in each of the...Ch. 7 - Suggest an explanation for the fact that...Ch. 7 - Prob. 41PCh. 7 - Write structural formulas for all the alkene...Ch. 7 - Prob. 43PCh. 7 - Prob. 44PCh. 7 - Predict the major organic product of each of the...Ch. 7 - Prob. 46PCh. 7 - Prob. 47PCh. 7 - The rate of the reaction In the first order in...Ch. 7 - Prob. 49PCh. 7 - Prob. 50PCh. 7 - You have available 2,2-dimethylcyclopentanol (A)...Ch. 7 - Prob. 52PCh. 7 - Prob. 53PCh. 7 - Prob. 54PCh. 7 - Acid-catalyzed dehydration of...Ch. 7 - The ratio of elimination to substitution is...Ch. 7 - Prob. 57PCh. 7 - Prob. 58DSPCh. 7 - Prob. 59DSPCh. 7 - Prob. 60DSPCh. 7 - Prob. 61DSPCh. 7 - A Mechanistic Preview of Addition Reactions The...Ch. 7 - Prob. 63DSPCh. 7 - Prob. 64DSPCh. 7 - Prob. 65DSP
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Propose a synthesis for the systemic agricultural fungicide tridemorph from dodecanoic acid (lauric acid), propene, and a one-carbon building block. How many stereoisomers are possible for tridemorph?arrow_forward(a) Draw and name all five isomers of formula C3H5F.(b) Draw all 12 acyclic (no rings) isomers of formula C4H7Br. Include stereoisomers.arrow_forwardClopidogrel is the generic name for Plavix, a drug used to prevent the formation of blood clots in patients that have a history of heart attacks or strokes. A single enantiomer of clopidogrel can be prepared in three steps from the chiral αhydroxy acid A. Identify B and C in the following reaction sequence, and designate the conguration of the enantiomer formed by this route as R or S.arrow_forward
- Following is an outline of a synthesis of the bronchodilator carbuterol, a beta-2 adrenergic blocker with high selectivity for airway smooth muscle receptors. Q. Is carbuterol chiral? If so, which of the possible stereoisomers are formed in this synthesis?arrow_forwardHow do you determine the stereochemistry of a compound using HNMR?arrow_forwardThuggacin C is a natural product with excellent biological activity. How many chirality centers does Thuggacin C have? a. 6 b. 7 c. 8 d. 9arrow_forward
- Following is the structure formula for Sertaline(Zoloft), widely prescribed to treat depression. Circle all the sterocenters present- how many stereoisomers of Zoloft are possible? Of these stereoisomers, how many are likely to be biologically effective in treating depression? Explain briefly.arrow_forwarda. Draw the 14 constitutional isomers of molecular formula C8H9Cl that contain a benzene ring. b.Name all compounds that contain a trisubstituted benzene ring. c.For which compound(s) are stereoisomers possible? Draw all possible stereoisomers.arrow_forwardCitalopram is an antidepressant pharmaceutical that is sold as a racemic mixture. However, it is known that the (S) enantiomer is 30x more biologically active than the (R) enantiomer. Draw the (S) configuration.arrow_forward
- Naproxen, a nonsteroidal anti-inflammatory drug that is the active ingredient in Aleve (p. 115), has a specific rotation of +66. One commercial preparation results in a mixture with a 97% enantiomeric excess. a. Does naproxen have the R or the S configuration? b. What percent of each enantiomer is obtained from the commercial preparation?arrow_forwardHexahelicene seems a poor candidate for optical activity because all its carbon atomsare sp2hybrids and presumably flat. Nevertheless, hexahelicene has been synthesized and separated into enantiomers. Its optical rotation is enormous: [a]D = 3700°.Explain why hexahelicene is optically active, and speculate as to why the rotation isso largearrow_forwardAn optically active unknown compound B, whose molecular formula is C6H10, reacts with H2/Ni produce compound C, whose molecular formula is C6H14. Compound C is optically inactive. What are the structures of compound B and C ?arrow_forward
arrow_back_ios
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning