Organometallic Cumulative Practice

Concept: Practice: Intro to Predict the Product

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Video Transcript

Now we're going to do some predict the product practice problems involving all the different reactions that organometallics can undergo. Keep in mind that some of these reactions, will be multiple step reactions. So what that means is that you may have to draw back from previous lessons in order to really figure out the entire thing.
At the end, just like always, I'll explain the answers to every problem. Let's go ahead and begin with problem one. 

Problem: Predict the product of the reaction

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Problem: Predict the product of the reaction

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Problem: Predict the product of the reaction

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Problem: Predict the product of the reaction

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Concept: Practice: Intro to Retrosynthesis

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Video Transcript

Now let's focus on some practice problems involving organometallics, but going the other way around. We want to do some retro-synthesis now. What that means is you're going to try to figure out what reagents it's going to take to make the final product. Think about all of the different reactions of organometallics we talked about and see how you can use them to your advantage in the next few questions.
Let's go ahead and try to do the first one. 

Problem: Propose a synthesis to accomplish the following transformation

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Problem: Propose a synthesis to accomplish the following transformation

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Problem: Predict the product of the reaction

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Organometallic Cumulative Practice Additional Practice Problems

Show how the following compounds could be synthesized from cyclohexanol.

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a. How many stereoisomers are obtained from the reaction of 2-pentanone with ethylmagnesium bromide followed by the addition of dilute acid?

b. How many stereoisomers are obtained from the reaction of 2-pentanone with methylmagnesium bromide followed by the addition of dilute acid?

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Suggest the most appropriate method for each of the following laboratory syntheses. In each case, suggest both a chromium reagent and a chromium-free reagent.

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Show two ways you could synthesize each of the following secondary alcohols by adding an appropriate Grignard reagent to an aldehyde.

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Show how you would synthesize the following primary alcohols by adding an appropriate Grignard reagent to formaldehyde.

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Predict the missing structures of products or reagents that you may use to accomplish the following transformations. Show the source of incorporation of deuterium and the stereochemistry when appropriate (No mechanism is required).

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Please provide regents, conditions, and desired products in the blank boxes for the synthetic scheme below.

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Provide the reagents necessary for the following conversion.

a) 1. CH3CH2MgBr/ether, 2. H3O+, Δ

b) 1. NaBH4/CH3OH, 2. CH3CH2MgBr

c) 1. H3O+ , CH3CH2MgBr/ether

d) CH3CH2MgBr/ether

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Draw the major organic product or reactant in the boxes provided for each reaction. Aqueous work up assumed where necessary.

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