CHE 331-800 10.10 - Chapter 5 Stereochemistry Chiral...

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Unformatted text preview: ' Chapter 5 Stereochemistry: Chiral Molecules Chapter 5 O lsomerism: Constitutional lsomers and Stereoisomers SUBDIVISION OF ISOMERS ISOMERS (Different compounds with same molecular formula) i’flgfi Constitutional isomers Stereoisomers (lsomers whose atoms have a (lsomers that have the same connectivity different connectivity) but that differ in the arrangement of their atoms in space) F—m'fww'me‘wi Diastcreomen (Stereoisomers that are not mirror images of each other) Enanh'omers (Stereoisomers that are nonsuperposabie mirror images of each other) Chapter 5 10/4/13 _ 6r % 11%-- Cl CI 0/ /'L/ :: C C 3 (L H 03 H :4 1 SC” In a! H \c’ I O A . K MDT 001 ((OF ‘l m E ‘6 L 0T -W o Enantlomers: stereoisomers whose molecules are nonsuperposable mirror images \ fit A chiral molecglp is one that is non-superimposable on its mirror image. 2-butanol is a chiral molecule. It contains a chirality center and can exist as a pair of enantiomers. to) Chapter 5 0 Diastereomers: stereoisomers whose molecules are not mirror images of each other Example: cis- and trans- double bond isomers Example: cis- and trans- cycloalkane isomers Chapter 5 10/4/13 . , m4f95 aech U600 scum“ Flame 5 M0! M Ma 270+ mm” WW5 10/4/13 23qu w some mommi- Properties of chiral molecules: ~k A molecule with a single tetrahedral carbon bonded to four different groups will always be chiral. * Switching any two groups at the tetrahedral center ‘ leads to the enantiomer in a molecule with one tetrahedral carbon. Stereogenic center: * An atom bearing groups of such nature that an Interchange of any two groups will produce a stereolsomer. * This can occur with either tetrahedral carbons or with ’ c=c double bonds. at , (IVW (3611' {90/1 l Muff 494 n , ’ CH3C1C=CHCH3 b+ereo an [C can it}, or T I or chit” ( C NW Stereogenic center stereogenic centers Chapter 5 2-propanol is an achiral molecule. It is superposable on its mirror image. This occurs when two or more groups on the tetrahedral carbon are the same. CH 3 H CH H C? VI 3 3 AOH H~640H HOKC’JJH H~é€|3A0H ‘ '~ I I ‘ V ICH l . CH3 CH33 safer mposab ' V VI VlO’r anal/131W Chapter 5 ,L r 616(70 04/) Which of the following molecules contain a chirality center? A. 3-chloropentaf)1e_wn’O 0 DP 8am o 5 V n M No dimming cc +cr O ntane B. 2-chlo ‘ . four (MW gmupfi H @ -cniraU+‘j WW C. 2-bromo—2-methylbutane 3></ a $0 Cfilfauhfi cmr . D. 3-bromo—3-methylpentane 0 NO CCn'leF Chapter 5 The Biological Importance of Chirality o 900% DWQ; 9H3 (S)—ibuprofen active 3 (R)-ibuprofen inactive Chapter 5 10/4/13 ...
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