Stereochemistry Based on McMurry's Organic Chemistry,6th edition,Chapter 9
Stereochemistry Based on McMurry’s Organic Chemistry, 6th edition, Chapter 9
Stereochemistry What is stereochemistry? study of the three-dimensional arrangement of atoms in molecules An object that is superimposable on its mirror image is achiral An object that is not superimposable on its mirror image is chiral
Stereochemistry What is stereochemistry? study of the three-dimensional arrangement of atoms in molecules An object that is superimposable on its mirror image is achiral An object that is not superimposable on its mirror image is chiral
Molecules that are different from their mirror image are called enantiomers CH X CH2XY CHXYZ Left hand Right hand
Molecules that are different from their mirror image are called enantiomers
Enantiomers and the Tetrahedral Carbon Lactic acid exists as a Mirror pair of enantiomers because there are H H four different gorups HO bonded to the central C-co.H H0,C一C0H H.C CH carbon atom (+)-Lactic acid (-)-Lactic acid H H Mismatch H Mismatch OH C -C HO- CO.,H HO CO,H CH Mismatch CH. HO- Mismatch CH3 H- -CO2H CO2H CH3
Enantiomers and the Tetrahedral Carbon Lactic acid exists as a pair of enantiomers because there are four different gorups bonded to the central carbon atom
The Reason for Handedness:Chirality Achiral molecule:has a plane of symmetry and is superimposable on its mirror image A plane of symmetry is a plane that passes through a molecule in such a way that what is on one side of the plane is the exact reflection of what is on the other side NOT Symmetry symmetry plane plane CH CH H H H OH CO,H CO,H OH CH CH2CO.H CH CHCO,H Propanoic acid Lactic acid (achiral) (chiral)
The Reason for Handedness: Chirality Achiral molecule: has a plane of symmetry and is superimposable on its mirror image A plane of symmetry is a plane that passes through a molecule in such a way that what is on one side of the plane is the exact reflection of what is on the other side