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1 9. Stereochemistry 立體化學 Based on McMurry’s Organic Chemistry , 7 th edition 2
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2 Stereochemistry 立體化學 ± Some objects are not the same as their mirror images as their mirror images ± A right-hand glove is different than a left-hand glove ± The property is commonly called handedness (用左手或右手的習慣) ± Organic molecules (including many drugs) 3 Organic molecules (including many drugs) have handedness Why this Chapter? Handedness is important in organic and biochemistry Molecular handedness makes possible specific interactions between enzymes and substrates 4
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3 OUTLINE ± Enantiomers and the Tetrahedral Carbon 對映異構物 ± The Reason for Handedness: Chirality 對掌性 ± Optical Activity 光學活性 5 ± Pasteur’s Discovery of Enantiomers (1849) OUTLINE ± Sequence Rules for Specification of Configuration 組態的規則 ± Diastereomers 非對映異構物 ± Meso Compounds 6 內消旋變體
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4 OUTLINE ± Physical Properties of Stereoisomers 立體異構物 ± Racemic Mixtures and Their Resolution 外消旋變體 離析 ± A Review of Isomerism Stereochemistry of Reactions: 7 ± Stereochemistry of Reactions: Addition of H 2 O to an AChiral Alkenes OUTLINE ± Stereochemistry of Reactions: Addition of H 2 O to a Chiral Alkenes ± Chirality at Nitrogen, Phosphorous, and Sulfur ± Prochirality 前手性 Chirality in Nature and Chiral Environments 8 ±
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5 Enantiomers – Mirror Images 對映異構物 Some molecules are the same as their mirror image 9 Some molecules are different than their mirror image These are stereoisomers called enantiomers Enantiomers and the Tetrahedral Carbon Enantiomers are molecules that are not the same as their mirror image They are the “same” if the positions of the atoms can coincide on a one-to-one basis (we test if they are superimposable 重疊鏡像 , which is imaginary) This is illustrated by enantiomers of lactic acid 10
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6 11 9.2 The Reason for Handedness: Chirality 對掌性 Molecules that are not superimposable with their mirror images are chiral (have handedness) 12
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7 Plane of Symmetry A molecule with a plane of symmetry is the same as its mirror image and is said to be achiral 13 The plane has the same thing on both sides for the flask There is no mirror plane for a hand Chirality Centers 對掌中心 A point in a molecule where four different groups (or atoms) are attached to carbon is called a chirality center 14 A chiral molecule usually has at least one chirality center
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8 15 Fig. 9-4, p. 292 Chirality Centers in Chiral Molecules 16
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9 17 WE 9.1 18
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10 P. 9.1 A)Screwdriver B)Screw C)Beanstalk D)Shoe 19 P. 9.1 20
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11 P. 9.2 21 P. 9.2 22
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12 P. 9.3 23 P. 9.3 24
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13 P. 9.4 25 P. 9.4 26
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This note was uploaded on 11/11/2010 for the course CHE CH2005 taught by Professor 曹恒光 during the Spring '10 term at National Central University.

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