Diels alder retrosynthesis problems


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Recall that E2 reactions prefer heat. Now that we have an asymmetric alkene we need an alkene addition reaction that will allow an alcohol to add onto a primary carbon or the anti-Markovnikov position.

MS 911 - Diels-Alder Practice

Hydroboration oxidation should immediately come to mind. And there we have it, a step by step transformation with reagents in place. This form of retrosynthetic analysis will help you quickly identify one intermediate at a time, all the way back to your starting molecule.

Retrosynthesis of Diels-Alder Reactions and Products

Reactant and product have a benzene ring. The product is a disubstituted benzene. The substituents have an ortho relationship. Which reactions do I know to carry out these transformations? Given that we have more than one reaction taking place, always pay attention to how the reactions impact each other.

We can add the nitro group through EAS Nitration. The groups are ortho to each other. But how do we ensure that we wind up with the ortho rather than para position? We need one more reaction that is not apparent in the product. We need a blocking group at the para position to ensure ortho is the only available group. All these thoughts should quickly run through your head. With para blocked we can carry out another reaction keeping in mind the following:.

BOTH groups direct to the 2 carbon near the ethyl group which is exactly what we want. N e xt we carry ou t EAS nitration forcing the ni tro group ortho to the ethyl and meta to the sulfate.


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Dilute acid will then remove the blocking group from the para position, leaving you with a nitro group meta to the ethyl group. They get so excited for having thought of all this that they forget that this is not the desired product. Ethyl is not our goal. We need a carboxylic acid. These same thoughts can be applied to any retrosynthesis problem from two through steps and more. Now that you have the basics for how to approach retrosynthesis, you will need a solid foundation.


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I recommend going back to review all the key reactions covered in your semester so you have them fresh and ready to utilize as needed. Do you feel better about retrosynthesis and staying on the right path to full credit for each problem? Let me know in the comments below. On the solution to the F. Where did the reduction come from to loose the oxygen? FC Acylation will add a carbonyl. We chose alkylation in this case because the carbonyl would direct meta.

We need an ortho directing group. The true key to successful mastery of alkene reactions lies in practice practice practice. However, … [Read More Click for additional cheat sheets. Click for additional MCAT tutorials. This video … [Read More Click for additional orgo tutorial videos. What do you think? Many students will look at the process and panic; And in said panic started drawing everything and anything that comes to mind, without a clear process or idea of where they are headed. As quickly as possible!

Retrosynthesis Organic Chemistry Tutorial -

Get every component and minimize lost points on your exam. How can I achieve this difference? Look for any non-carbon atoms and functional groups.

Look for location of reactivity on the molecule. This allows us to carry out a number of reactions: Elimination to create a pi bond E1 or E2 Substitution to give us another functional group in the form of an incoming nucleophile SN1 or SN2 We could turn the Cl into a Grignard for a super reactive organometallic And so much more… This is your clue regarding WHERE to start the reaction. Compare each of these features to the final product. If the number of carbon atoms changed, by how many? How many carbons were added or removed?


  • Mechanism of the Diels-Alder Reaction.
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If the functional groups or reactivity changed , what was replaced and by what? How many new groups were added? This is a two-part question. This is where the true power of retrosynthetic analysis comes into play. Comparing the reactant to the alkene, Do I know of a reaction that will either carry out this transformation or get me close? Now ask yourself this: Which reagent will carry out each transformation?

Start with backwards thinking whenever you can. Sulfur is partially positive and a meta directing group. This is where many students lose points. What have we forgotten? Comments Saifullah Khan Yousafzai says:.

From Wikipedia, the free encyclopedia

April 1, at am. Quality practice questions and problem sets for organic chemistry. Description: Diels Alder stuff- predict the products, retrosynthesis, and. But how do chemists make these complex molecules? One important reaction for synthetic chemists is called the Diels-Alder reaction. This type of reaction uses.

Diels-Alder stereochemistry is defined by the so-called endo rule or cis endo rule. Unfortunately You do not need to turn problems getting the right answer. In organic chemistry, the Diels—Alder reaction is a chemical reaction between a conjugated.. The problem is that ketene itself cannot be used in Diels—Alder reactions because it reacts with dienes in Thus activation by strongly Lewis acidic cupric tetrafluoroborate was required to allow for the reaction to take place. The Diels-Alder reaction is favored by electron withdrawing groups on the dienophile and electron donating groups on the diene.

Good Dienophiles: O. As noted previously, the Diels Alder reaction is a classic example of a The diene and dienophile in the Diels Alder reaction.

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