Diastereomers Stereoisomers:

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Presentation transcript:

Diastereomers Stereoisomers: same molecular formula, same bonding arrangement, different spatial arrangement Enantiomers: two stereoisomers that are nonsuperimposable mirror images Diastereomers: stereoisomers that are NOT mirror images

Diastereomers In general, diastereomers fall into two categories: geometric isomers cis-trans compounds containing two or more asymmetric atoms (but not mirror images)

Fischer Projections Fischer Projections are often used to depict stereochemistry when more than one asymmetric carbon is present. Left and Right come toward you. Top and Bottom go away from you.

Fischer Projections Rules for using Fischer Projections: Carbon chain is drawn along the vertical line of the Fischer Projection C # 1 at the top asymmetric carbon where the lines cross Vertical lines: bonds going away from you Horizontal lines: bonds coming towards you

Fischer Projections = = = Rules for using Fischer Projections: Structures can be rotated by 180o only. Rotation by 90o is NOT allowed. You cannot flip over a Fischer Projection. = = =

Fischer Projections s Fischer Projections are useful when: drawing mirror images identifying internal mirror planes of symmetry s

Fischer Projections superimposable Fischer Projections are useful when: determining if two substances are nonsuperimposable mirror images remember to follow the rules for using Fischer Projections rotate 180o superimposable

Stereochemical Relationships On your exam, you must be able to identify the relationship between two structures. Different compounds that are not isomers Same compounds Enantiomers Diastereomers

Stereochemical Relationships Different compounds, not isomers: Different molecular formulas Structural (constitutional) isomers: Same molecular formula, different bonding pattern

Stereochemical Relationships Same Compound: Same molecular formula, same bonding pattern All sets of equivalent asymmetric carbons will have the same configurations

Stereochemical Relationships Enantiomers: Same molecular formula, same bonding pattern All sets of equivalent asymmetric carbons will have the opposite configuration

Stereochemical Relationships Diastereomers: Same molecular formula, same bonding pattern At least one set of equivalent asymmetric carbons has the same configuration AND At least one set of equivalent asymmetric carbons has the opposite configuration

Stereochemical Relationships Example: Determine the relationship between the following pairs of compounds.

Identifying All Possible Stereoisomers A compound with “n” asymmetric carbon atoms can have a maximum of 2n stereoisomers. Example: What is the maximum number of stereoisomers for each of the following compounds? 2,3-dibromobutane 2,3-dibromo-5-methyloctane

Identifying All Possible Stereoisomers 2,3-dibromobutane only has 3 distinctly different stereoisomers: enantiomers What is the relationship between the compounds above and below? s s Same compound

Identifying All Possible Stereoisomers Example: Draw 3-d structures of all possible stereoisomers of 2,3-dichloropentane. Which ones are chiral? Name each one. Give the stereochemical relationship between them.

Identifying All Possible Stereoisomers

Identifying All Possible Stereoisomers

Review Example: Is the following compound chiral? Name the compound.

Review Example: Is the following compound chiral? What is the maximum number of stereoisomers possible for this compound. Draw one possible diastereomer of this compound.