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Chem 301 (Organic Chemistry One)- Week 8

by: Jayda Abrams

Chem 301 (Organic Chemistry One)- Week 8 Chem 301

Marketplace > Virginia Commonwealth University > Chemistry > Chem 301 > Chem 301 Organic Chemistry One Week 8
Jayda Abrams
Virginia Commonwealth University
GPA 3.52

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Notes about Chirality and Fischer Projections covered on Exam 2.
Organic Chemistry 1
Jon Baker
Class Notes
Organic Chemistry
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This 4 page Class Notes was uploaded by Jayda Abrams on Sunday August 21, 2016. The Class Notes belongs to Chem 301 at Virginia Commonwealth University taught by Jon Baker in Fall 2016. Since its upload, it has received 17 views. For similar materials see Organic Chemistry 1 in Chemistry at Virginia Commonwealth University.

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Date Created: 08/21/16
Chapter 5 All about Chirality!: Objects that have a left handed and right handed version of each other are chiral. This includes hands, feet, shoes and gloves. It can be said that the left and right handed versions of an object can be described as mirror images. Objects that are not chiral (or do not have a left and right handed version of each other/or are not mirror images of each other) are achiral. Achiral objects include a chair, a spoon or a cup of water. The difference between chiral and achiral can be remembered like this: RAL= Right and left. This is because chiral objects have a CHIRAL RIGHT AND LEFT version of each other! A…RAL= Anti Right and Left. This is because achiral objects ACHIRAL do NOT have a RIGHT AND LEFT version of each other. Two objects are said to be superimposable if one of the objects can lay on top of the mirror image of the other object perfectly and have all the pieces line up. To draw the mirror image of a molecule draw the same structure with the left and the right reversed! Notice that the structure of the molecule is unchanged! However in picture one the CH3 group is on the left and in picture two it is on the right. In picture one the hydrogen is on the right and in picture two it is on the left. Also notice how in both picture the carbon is in the center and the COOH group is still going up. The OH group is on a wedge in BOTH pictures and the H group is on a dash in both pictures! Nothing else has changed except the side the groups are on! How do you Know If a Molecule is Chiral?: The most common distinguishing factor of a chiral molecule is a carbon atom bonded to four different groups. A carbon with four different groups is also called an asymmetrical carbon atom and can be designated with an * beside it. An asymmetric carbon is the most common example of a chiral center (or a chirality center). Chirality centers belong to a group called stereocenters and stereocenter belong to stereoisomers. The best test for chirality is to determine if the molecule’s mirror image is the same or if it is different. If a compound does not have any asymmetric carbons it is achiral. If a compound has one asymmetric carbon it is chiral. If a compound has more than one asymmetric carbon it can be chiral or achiral. Any molecule that has an internal mirror plane of symmetry cannot be chiral (even though it may have asymmetric carbon atoms). Enantiomers (stereoisomers that ARE mirror images of each other) are told apart by the way they rotate polarized light. All the other properties (boiling point, melting point and density) are the same! The difference between two enantiomers can be specified by classifying the molecule as R or S. This is done by the Cahn-Ingold-Prelog Convention. Here is the procedure: 1. Assign priority to the groups- Atoms with a higher atomic number receive a higher priority. The highest priority should be numbered 1 and the lowest should be numbered 4. In most cases (but not always) hydrogen will be the lowest priority group. Make sure you are only looking at the FIRST atom of the group! *If there is a tie continue until the tie is broken! This is done by finding the higher priority group by comparing two groups. Make sure you are only looking at ONE atom at a time! *Treat double and triple bonds as if they are separate atoms. 2. Put the fourth priority group in the back- Use a 3D drawing or a 3D structure. 3. Assign R or S- Connect groups 1-3 in numerical order. If the arrow points clockwise it is R if it points counter clockwise it is S. If the fourth priority group is in the plane you can switch the number of the fourth priority and the one going back. After that you reverse the letter. If it is R it changes to S if it is S it changes to R. Fischer Projections Everytime I think of a Fischer projection I think of this part of the Patty Hype Spongebob episode. This helps me because the fry helps me remember the set up of a Fischer projection. When placing particals on a Fischer projection the wedges are placed horizontally (like the fry’s bowtie) and the dashes are placed vertically (like the crinkle cut of the fry.) This picture helps with the process of converting a drawing into a Fischer projection or placing parts on a Fischer projection however it does not represent the final drawing. Unlike a line angle drawing Fischer projections do not show dashes and wedges and the final projection has all lines “in the plane” with the chiral carbon in the center. It is important to know that Fischer projections are used for compounds with two or more asymmetric carbon atoms. They can be rotated by 180 degrees because the vertical lines will still be vertical and the horizontal lines will still be horizontal. However they cannot be rotated 90 degrees. Rotating a Fischer by 90 degrees would produce an enantiomer (Type of stereoisomer that has mirror images at the stereo-center(s)). When naming a Fischer projection with the IUPAC system the longest carbon chain will be the vertical line (line running from top to bottom). Process of converting a line angle to Fischer projection: C C The picture shows the first diagram that we are familiar with carbon in the middle with four groups coming off of it. The second diagram shows those same four groups on the bowtie french-fry. The bow tie acts as the wedges and the crinkle cut acts as the dashes. The groups are placed where they are because the angle observed to make this conversion. The observer would be looking up from the bottom between the red and yellow group. Meaning the red and yellow group would be coming forward which is why they are on the bowtie, and the green and purple group would be going back which is why they are on the crinkle part. The last diagrams shows the exact same thing without the dashes and wedges in the diagram and this is the final projection. Drawing Mirror Images of Fischer Projections The biggest part of drawing any type of perspective drawing is remembering to reverse the right and left and keeping the up and down (or front and back) in the same position. Swapping out the groups on the horizontal part of the cross is the key part of creating a mirror image of a Fischer projection because this completes half of the work. The other half is complete because the vertical groups are not changing and have not moved. It is important to know that interchanging the groups on the horizontal part of the diagram will reverse the R and S configuration. If something is R it turns to S and if something is S it turns to R. Testing for enantiomers is important and simple with Fischer projections. If the mirror image cannot be made to look the same as the original with a 180˚ degree rotation then the two mirror images are enantiomers. If the mirror images are the same the structure is achiral. Original Mirror Image 180 Rotation If the mirror images are different then the structure is chiral. In Fischer projection the planes of symmetry can also run horizontal. If they do the structure is chiral. Original Mirror Image 180 Rotation


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