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 2 n , where n is equal to the number of chirality centers. 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.

Question

Want to see the full answer?

Answer 1

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 2n, where n is equal to the number of chirality centers.

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 solution

See solution

Students 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?