Stereochemistry. Stereochemistry: – The study of the three-dimensional structure of molecules Structural (constitutional) isomers: – same molecular formula.

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Presentation transcript:

Stereochemistry

Stereochemistry: – The study of the three-dimensional structure of molecules Structural (constitutional) isomers: – same molecular formula but different bonding sequence Stereoisomers: – same molecular formula, same bonding sequence, different spatial orientation

The properties of many drugs depends on their stereochemistry: (S)-ketamine (R)-ketamine anesthetichallucinogen

Optical Isomerism Optical Activity The property of the substance to rotate the plane of the plane-polarized light is known as optical activity. - Dextro-rotatory (+) - Laevorotatory (- ) Necessary condition: Molecule should be dissymmetric. Example: Biphenyl 2, 2’ – disulphonic acid

Enantiomers Enantiomers are defined as the isomers where molecular Structures are mirror images of each other and which rotate the plane of the polarized light equally but in opposite directions. - Properties of enantiomers Chirality is the necessary and sufficient condition for the existence of enantiomers.

Chiral vs. Achiral Example: Identify the following molecules as chiral or achiral.

Diastereomers Pair of molecules with two or more different chiral carbon atoms which are neither identical nor non- superimposable mirror images of each other.

Enantiomers Enantiomers nonsuperimposible mirror images

Meso Compound A compound with two or more asymmetric carbon atoms but also having a plane of symmetry (a mirror plane) is called the Meso compound.

Meso Compound Meso Compound Internal Plane of Symmetry Optically Inactive

Absolute Configuration

Assign Priority to each Group on Asymmetric Center Example priorities: I > Br > Cl > S > F > O > N > 13 C > 12 C > 3 H > 2 H > 1 H

Lactic Acid

C.I.P. Priorities

(R) and (S) Nomenclature The two enantiomers of alanine are: Natural alanineUnnatural alanine (S)-alanine(R)-alanine

(R) and (S) Nomenclature CH(CH 3 ) 2 > CH 2 CH 2 Br > CH 3 CH

Fischer Projections

Assigning Absolute Configuration to Fischer Projections

Fischer Projections with 2 Chiral Centers

Tartaric Acids

2,3,4-trichlorohexane How many stereoisomers?

n = 3; 2 n = 8

A Carbohydrate

Reactions that Generate Chirality Centers Hydrogenation, syn

Bromination Trans is formed exclusively No Meso is formed (cis)