Organic Chemistry 2230: Chapter 4 Part B and Chapter 5 Part A
Organic Chemistry 2230: Chapter 4 Part B and Chapter 5 Part A Chemistry 2230
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This 3 page Class Notes was uploaded by Amanda Biddlecome on Friday February 19, 2016. The Class Notes belongs to Chemistry 2230 at Clemson University taught by Dr. Schroeder in Fall 2016. Since its upload, it has received 27 views.
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Date Created: 02/19/16
Organic Chemistry 2230 Chapter 4 Part B February 19, 2016 Amanda Biddlecome 1) Stereoisomers and Chirality -‐mirror images=enantiomers with different spins -‐don’t mirror image and swap bonds from the original because they would be identical -‐downfall to Newman is that you can’t see back carbons -‐Sawhorse Diagram *carbon on bottom=front carbon *carbon on top=back carbon *halfway between skeletal and Newman when looking at it *benefits are that you can see the carbon and nothing else changes from the Newman Projection -‐Fischer Projection *starts with staggered Newman Projection, make it eclipsed, flip it up onto its side *four wedges point at you, two dashes point away from you -‐spins in all projections *Newman: find the chiral carbon and pick it up to look with the lowest priority behind *Fischer Projection: count it with it laying normally but make sure #4 doesn’t face you and if it is, flip the spin -‐chiral carbons *anything not sp hybridized, you ignore it *put wedges and dashes anywhere you want, as long as they are adjacent to one another (lowest priority in the back) *any structure with a chiral will automatically have two possible structures: mirror images *don’t put wedges and dashes inside a ring (give dash and wedge to two things coming off of the ring) 2) Optical Activity and Polarized Light -‐light is random and in waves -‐polarize gives order to disorder -‐achiral=no chiral carbons -‐use clear glass of water and shine a light through it *light comes out just as it went in -‐use sugar water *light comes out spiraling because of chiral carbon -‐optically active means it has chiral carbons *compound that rotates polarized light *antichiral=not active -‐dextrorotary=rotates to the right (+) -‐levorotary=rotates to the left (-‐) *only how it rotates light, but it’s different than what we’ve been learning (doesn’t refer to how structure is put together, just what it does) 3) Stereochemistry and Chirality -‐2 chiral carbons *need two letters *can get four different structures by changing dashes and wedges *Diastereomers=pair of molecules with more than one chiral carbon and at least two of them share a spin *Enantiomers=more than one chiral carbon with at least two with opposite spins *the number of structures=2 ; n=number of chiral carbons n -‐Tartic acid *two chiral carbons: find the two spins, reflect them and get mirror images and enantiomers (two more to go now so set up another pair), draw a new fischer projection with switched locations for substituents -‐Meso Compounds *pair of compounds with internal symmetry plane *enantiomers, but more specific -‐just because there’s a wedge doesn’t mean it’s a chiral carbon 4) Stereochemistry and Pharmaceuticals -‐Prozac *enantiomers: separating them is very difficult *(S)=good but metabolizes quickly, so use a mixture of (R) and (S) to balance it out -‐receptors=bonding sites for enzymes *some enantiomers don’t bind properly Chapter 5 Part A 1) Alkenes -‐double bonds -‐alkanes with double bonds, change the end from –ane to –ene *example: butane to butane -‐all double bonds end in –ene *put the number in front of parent to show where the double bond is -‐saturated compound=completely full *molecule that can’t accommodate anymore hydrogens *C H n 2n+2 -‐unsaturated compound=incomplete *don’t have the maximum number of hydrogen *C H n 2n-‐2 *rings -‐degree of unsaturation *tells how many pi bonds or rings in a molecule *should have one pi bond for every two hydrogen atoms removed *take the number of hydrogen needed to make it saturated, subtracted the number that is there, divide by two
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