Structural, Geometric, Enantiomer Isomers Structural, Geometric, Enantiomer

Isomers Compounds that have the same molecular formula but difference structure and different properties 3 types: Structural isomers Geometric isomers Enantiomers

Structural Isomer same KIND and AMOUNT of atoms (molecular formula) but the atoms have different connectivity Structural isomers usually have different physical and chemical properties

Structural Isomer

Structural Isomer

Structural Isomer

Structural Isomer

Structural Isomer How many different structures can you make from C5H12?

Geometric Isomers SAME molecular formula and the SAME connectivity but different spatial arrangements Due to inflexibility of a bond, usually either: double bonds (cis and trans formation) bonds that can’t rotate (i.e. in a ring formation)

Geometric Isomers

Geometric Isomer Why is example 1 not a pair of geometric isomers? Hint: Look at example 2 & 3 and compare to example 1. What is the minimum requirement for a pair of molecules to be considered geometric isomers?

Geometric Isomer Answer: Each carbon of the double bond must have two different substituent groups So if example 1 is not a pair of geometric isomers, what are they classified as?

Geometric Isomer Another type of geometric isomer is found in ring structures and doesn’t involve double bonds Due to the inflexible nature of the bonds that make up the ring Note: The ring lies on a flat plane (e.g. your paper) and the OH groups are perpendicular to the plane (e.g. up and down)

Enantiomer Molecules that are mirror images of each other Note: left and right hands are a pair of enantiomers (mirror images not identical) What other body parts that are enantiomers?

Enantiomer Activity: Build these molecule pairs Compare them to determine whether they are enantiomers

Enantiomer

Enantiomer How are the lower pairs of molecules different from the upper pairs? What condition do you think is necessary for a pair of molecules to be enantiomers? X

Enantiomer Requirement: Enantiomers can only occur when each of the four groups attached to the central carbon atom are all different. The central carbon is known as a chiral carbon and the molecule is chiral.

Chiral Molecules Asymmetric carbon: carbon with 4 different groups bonded to it No plane of symmetry Mirror image is non-superimposable

Achiral Molecule lacks chiral properties has a plane of symmetry

Practice: Identify the chiral carbons Double bond to carbon = achiral

Application: Amino acids Amino acids are building blocks of proteins Some amino acids can exist as enantiomers because of their chiralty Switching an enantiomer in a biological system can have detrimental effects

Application: Enzymes Enzymes are always chiral. Their binding sites are in a specific orientation that fits only one form of an enantiomer. Binding sites won’t fit if the wrong enantiomer is present.

Racemic mixture A mixture that contains equal quantities of both enantiomers Enantiomers can interconvert in vivo

Racemic mixture Story of thalidomide (1960’s) A racemic drug given to pregnant women to combat morning sickness One of the enantiomers caused birth defects (teratogen) and death http://www.thalidomide.ca/the-canadian-tragedy/

Racemic mixture What’s in Advil (ibuprofen)? Production results in a racemic mixture One of the enantiomers is effective as an anti-inflammatory Takes about 30 minutes for the inactive enantiomer to be converted http://www.brookscole.com/chemistry_d/templates/student_resources/0534389996_mcmurry/CHEM_A_WORK/chapter9.htm The World of Chemistry, 4 ed. 2007. Thomson Brooks/Cole. Joesten, Castellion, & Hogg.

Steps to identifying isomers Do the molecules have the same chemical formula? If the formula is different, they are NOT isomers but completely different molecules Are the molecules identical? If they are, they are NOT isomers. Are all the atoms connected in the same way to other atoms? If not, they are STRUCTURAL isomers Look for an inflexible bond (double bond or ring) for geometric isomers Look for mirror images for enantiomers http://2.bp.blogspot.com/_K91FA3B4cpM/SJ_NUmBWWGI/AAAAAAAAACY/UzL8H8Q4oag/s400/ist2_1744503_frustration.jpg

Summary Isomer Same Different Requirements Structural Geometric Enantiomer

Summary Isomer Same Different Requirements Structural Molecular formula Connectivity Geometric Enantiomer

Summary Isomer Same Different Requirements Structural Molecular formula Connectivity Geometric Molecular formula & connectivity Spatial arrangement Double bond Different substituent groups on each carbon Enantiomer

Summary Isomer Same Different Requirements Structural Molecular formula Connectivity Geometric Molecular formula & connectivity Spatial arrangement Double bond Different substituent groups on each carbon Enantiomer Chiral molecules Mirror image

Practice: Identify the chiral carbon

Practice: Identify the chiral carbon * * * * * *

Practice: Identify the chiral carbons structural isomers structural isomers geometric isomers

Practice: Identify the chiral carbons * structural isomers * * * * * * * * * structural isomers geometric isomers * * * *