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Copy of L,D and R,S Optical Isomers

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herman faes

on 17 March 2013

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Transcript of Copy of L,D and R,S Optical Isomers

Optical Isomers
L,D and R,S Optical Isomers What is an Optical Isomer? Two mirror images of chiral molecules Chiral is a non-superimposible mirror image Have many identical properties Polarized Light Optical isomers have the ability to rotate the plane of polarized light When passed through solution containing optical isomers, the plane of polarization is rotated either to the left or the right Naming Three Ways of Naming l- and d- R- and S- D- and L- d- and l- Discovered by Louis Pasteur d- (dextrorotatory)
Left and (+) l- (levorotatory)
Right and (-) D and L Designations D and L are stereoisomers D and L sugars are mirror images of one another In sugars, the D and L designation is determined by the placement of the hydroxyl group D and L D and L do not determine the rotation of the plane of polarized light The number of stereoisomers
is 2^n d- and l- Anything that rotates the plane of polarized light is called optically active Sugars are optically active because of their asymmetric centers, commonly included in the name D (+) glucose or D (-) fructose R and S Designations Most important nomenclature system for naming optical isomers Labels the center of the chiral molecule as either R or S Naming R and S Step 1: Using Cahn-Ingold-Prelog, assign priorities from 1 through 4 to the four groups bonded to the chirality center Step 2: Position molecule so that the 4 group is fathest away from you Step 3: Determine if the arragement goes clockwise or counterclockwise Examples Optical Isomers (Stereoisomers) Examples of optical isomers or stereoisomers include:
Carvone
Thalidomide
Methamphetamine
Ephedrine
Epinephrine Carvone Chemicals and different things you come in contact with in the environment have different smells due to their stereochemistry The stereochemistry of things alters the way in which it influences the olfactory receptors Spearmint leaves contain (R)- carvone Caraway seeds contain (S)-carvone Smell differently to most people Caraway seeds Spearming Leaves Epinephrine (Adrenaline) Hormone and neurotransmitter
Chirality influences how well different chemicals are able to interact with receptor sites in the body.
One enantiomer may effect the body more and provoke a greater biological response then its counterpart
(-)-(R)-Epinephrine is more active then (+)-(S)-Epinephrine
(-)-(R)-Epinephrine therefore reacts with receptor sites better
A racemic mixture of epinephrine is used to treat croup, which is difficulty breathing accompanied by a barking sound when you cough and swelling around the vocal cords Thalidomide Exists as optical isomers or enantiomers (R) and (S)
(R) is effective against insomnia, and morning sickness (effective)
(S) is teratogenic, causing birth and limb defects in children born to mothers who take it (harmful side effects)

Enzymes in your body are only able to recognize one of the enantiomers due to the active site Methamphetamine Methamphetamine stimulates the CNS, it affects brain neurotransmitters, including dopamine, serotonin, and norepinepherine
Sympathomimetic drug (Stimulant), increases heart rate, bp, and is used to treat asthma, ADHD, obesity and narcolepsy
(R) Isomer- Legal, it’s used in inhalers for nasal decongestion, works by constricting blood vessels, and inflammation and swelling
(S) Isomer- Illegal, Stimulant known as speed, this causes euphoria and pleasure and is highly addictive Methamphetamine Alain Baxter tested positive in 2002 for methamphetamine after winning the bronze medal in alpine skiing in Salt Lake.
20 millionths of a gram of a banned substance, Methamphetamine, were found in his urine during a post race drug test
He was using a Vicks Vapor Inhaler which contains the (R) Isomer which is legal and not the (S) Isomer which is actually illegal. Ephedrine/ Pseudoephedrine Comes from the Ephedra plant
It is used as a stimulant, appetite suppressant, and a nasal decongestant
(1R,2S) Ephedrine and (1S,2S)Pseudoephedrine,work the best Ephedrine/ Pseudoephedrine (1S,2S)Pseudoephedrine is contained in Sudafed to help with nasal decongestion

(1R,2S) Ephedrine is used in weight loss and diet pills, it increases the metabolic rate

Ephedrine has been linked to lots of health issues and was banned in the U.S. by the FDA in 2006 Cited Sources Cited Sources Smith, M. Organic chemistry, an acid-base approach. 2. CRC, 2011. 343-399. Print.
http://news.bbc.co.uk/winterolympics2002/hi/english/alpine_skiing/newsid_2341000/2341143.stm
http://lawrencekok.blogspot.com/2011/06/ib-chemistry-stereoisomerism-optical_25.html
http://en.wikipedia.org/wiki/Racemic_epinephrine
http://www.ncbi.nlm.nih.gov/pubmedhealth/PMH0001955/
http://altmedicine.about.com/cs/allergiesasthma/a/Ephedra.htm
http://www.nlm.nih.gov/changingthefaceofmedicine/physicians/biography_182.html
http://www.cliffsnotes.com/study_guide/CahnIngoldPrelog-RS-Notational-System.topicArticleId-22667,articleId-22649.html
http://www.askthenerd.com/NOW/CH7/7_3.pdf
http://www.rpi.edu/dept/bcbp/molbiochem/MBWeb/mb1/part2/sugar.htm
http://www.mz-at.de/pdf/RegisChiralReview.pdf
http://www.elmhurst.edu/~chm/vchembook/209optical.html
http://en.m.wikipedia.org/wiki/Chirality_(chemistry)
http://www.chemistryinyourcupboard.org/nurofen/3
http://www.youtube.com/watch?feature=player_embedded&v=3WZZXPOsPNI By: Katie Kasper, Miranda Gerry, and Heidi Dubois
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