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Week 11- L20,L21,L22

by: Hayley Lecker

Week 11- L20,L21,L22 CHEM 2325 - 001

Hayley Lecker
GPA 3.42

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Sorry for this being late my husband's grandfather died and I was busy saturday and sunday making plans for him to go AZ. However, this covers the three lessons for the week.
Organic Chemistry - 12551
James Salvador
Class Notes
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This 16 page Class Notes was uploaded by Hayley Lecker on Monday April 4, 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 56 views.


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Date Created: 04/04/16
OrganicChemistry 2Week 11 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! L20 In this lesson it’s pretty easy, just you have to pay attention to what it asks for. In this first problem, the acid starts the reaction. There is a substitution of one of the hydrogens ortho to the ketone group with the bromine atom. This is where I am talking about paying attention to the reaction, you have to know what comes first because that determines the product. In this the methyl adds to the same position as the other methyl. This is just the structure of LDA- REMEMBER THE NAME LITHIUM DI…AND LDA! This is an important intermediate, when pyrrolidine is added it creates the structure below which makes substitution easy. In this example the LDA comes after the hexanone, if the LDA came first the methyl group would have added to the other side of the ketone and not the same side of the methyl group. An example of LDA reacting. In this example the t-butyl group is adding in a backside attack, it is same side as the methyl because LDA was added secondly. This is example of LDA being added first, it creates a double bond on the opposite side the ketone group, if iodomethane was added the oxygen would rebond and the methyl would add to that side, but because Si(CH3)3 Cl was added it is more likely to attack the oxygen. L21 This lesson was both drawing (huge structures) and reactions. I did not explain the first two problems since they were drawing, so this is a condensation reaction, it reactions with itself to create a ring. In this reaction the propanone reactions with itself. A double bond forms where the “Second” oxygen would be to connect the two structures. Remember chirality. This is another example of the two molecules reacting with each other. You want to make a 5 or 6 membered ring only! First draw it out and count, in this case a 5 membered ring will be made with the loss of two hydrogens and 1 oxygen. This is a slightly more complicated example. This is where the cyclo ring reacts with itself. In the addition project you end up with the two structure adding together but instead of a double bond, an alcohol is formed. L22 When you react in a Claisen if it can’t react with only itself it will reaction with another molecule and make a structure like this, think of ONE molecule plus half of the other. This is an example of it reacting with itself, we have a loss of the OEt group, and a six membered ring was formed. First reaction ethylacetoacetate together, then proceed. The base allows so the 3-bromo can react, the by products are the OEt group and HBr. This was just naming. More naming, I didn’t get much naming hopefully you do! Remember first react, then move on. So excess ethyl bezonate adds a benzene ring. Another naming, this was about the hardest the naming got. Another example of the two structure reacting, if you notice the ethanoate reacts at the one positon (since there is only two carbons) but propanoate reacts at the two position since it makes the most stable carbon cation. React first, the base with H&H removes the ethyl and additional ketone group.


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