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Week 4 notes on S2 and L9

by: Hayley Lecker

Week 4 notes on S2 and L9 CHEM 2325 - 001

Hayley Lecker
GPA 3.42

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About this Document

I covered S2, an extension on S1. L9 is also covered and covers chirality in dienes (Cumulenes).
Organic Chemistry - 12551
James Salvador
Class Notes
Organic Chemistry, UTEP, University of Texas at El Paso, Ochem, Organic Chemistry 2
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This 9 page Class Notes was uploaded by Hayley Lecker on Thursday February 11, 2016. The Class Notes belongs to CHEM 2325 - 001 at University of Texas at El Paso taught by James Salvador in Fall 2015. Since its upload, it has received 91 views.


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Date Created: 02/11/16
OrganicChemistry 2Week 4 Important Information: Professor’s Email: Class Website: Class Code (E-book): utep2325spring2016 Includes examples of the Homework! Posted the week before the homework’s are due to help everyone get 100’s! S2: Cascarillic Acid For this homework I will walk you through steps 6-8 since the other steps are just like the Leaf Alcohol but just with a different alkene being attached. If you don’t know how to do those steps please refer to Week 3 note packet. Step 1: Step 2: Step 3: Step 4: Step 5: Step 6: This is the step where leaf alcohol stopped, but cascarillic acid does not. The Lindar Catalyst converts the triple bond to a double bond where the hydrogens are cis. Step 7: Now in this step diiodomethane with ZnCu converts the diiodomethane into a CH2, which comes in and breaks the double bond. This forms a ring as seen. You can also observe that the hydrogens are still CIS! Step 8: Sorry for the blurriness my computer crashed and I lost this picture so I had to take a screenshot off my phone so its small! In the final step, the only thing changed is the once alcohol group hanging off to the leaf. It is converted in to a carboxylic acid. So a double bonded oxygen is added to the carbon that the alcohol is already bonded too. ALSO MAKE SURE YOU CHECK FOR CIS! The hydrogens as you can see are still both upward! L9 Cumulenes Cumlenes means one have the other, so double bonds will be next to each other. Cumulenes can have chirality but will have no chiral centers because of being an even number. While a chiral center is asymmetry in a molecule, chirality is the symmetry of the whole molecule. In the homework example I will show how to see the chirality of a molecule. Homework Examples: Example 1: Draw (R)-penta-2,3-diene First step: DRAW it out first, as you can below that is the molecule drawn out. Now, the second picture below it shows how to check for the chirality. So you want to turn it, like a Newman Projection, so you are looking down the carbons making the double bond. Then you go from priority one on the front side to priority two, whichever is the “smallest” path. In this example, you go from the methyl on the right to the methyl on the left, because it is clockwise it is R like we needed. Example 2: Draw (Z)-hexa-2,3,4-triene During the lesson you have to remember Z and E, Z means priority one on each side is cis. Example 3: Draw (E)-hexa-2,3,4-triene During the lesson you have to remember Z and E, E means priority one on each side is trans. Example 4: Draw 4-methylpenta-1,2,3-triene This is an example of one with a methyl. First draw out the skeleton structure with only the double bonds, then add in the methyl so you don’t add it in wrong. Example 5: Draw (S)-penta-2,3,-diene So, this is like the first example, but I wanted to show you what S looks like. So do the exact same as the first example, but if when you line it up its R just press mirror and it will be S configuration.


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