What alkyl halide reacts with lithium divinylcuprate [(CH 2 =CH) 2 CuLi] for the synthesis of each of the following compounds? c. d.

Hello everyone. So this video, we have to provide the alco chloride that were wrapped with our organic crate to give us the following product. So of course, the molecule one here as an Alcaine and molecule two here is an alkene. So thinking retro synthetically, our r group of the organ coping molecule is the C H three C H two group as indicated here. So that will be our two carbons that are from our products starting off with this molecule here, the two carbons. Again, we have to remember that it's from the organo rate. So we have one and two carbons here that we don't need to worry about. So we kind of just cut this bond here. And if we do so on the left side here, we'll get our alky chloride. So we have this three carbon chain connected to a chlorine atom. And over to the right we have of course, again, the organ of group rate. So let's draw that structure out. All right. So that's going to be the alkyl fluoride for our reaction here. So we go ahead and highlight that as the final answer for part one and moving on to part two. Here. Again, we have two carbons coming from the organo crores. So we have one and two. We go ahead and cut off that bond. So that again is our while you here, the organo crate then over to the left, we'll have our alco chloride. So this time we just have a double bond but nothing else changes here. So we go ahead and circle that as to be the final alco chloride for part two. So get over to the left, we have this linear chain to be the alco chloride over to the right for molecule two, we'll just have a double bond.

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1. A Review of General Chemistry5h 5m
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3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
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21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
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13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

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1:56 minutes

Problem 32c,d

Textbook Question

What alkyl halide reacts with lithium divinylcuprate [(CH₂=CH)₂CuLi] for the synthesis of each of the following compounds?
c.
d.

Verified step by step guidance

Step 1: Analyze the target compounds (c and d) provided in the image. Compound c is a linear alkene with two vinyl groups added to a straight-chain alkyl group. Compound d is a branched alkene with two vinyl groups added to a branched alkyl group.

Step 2: Understand the role of lithium divinylcuprate (3(CH2=CH)2CuLi4). This reagent is used for conjugate addition of vinyl groups to alkyl halides. The reaction involves the replacement of a halide group with vinyl groups.

Step 3: For compound c, identify the alkyl halide precursor. The target structure suggests that the starting alkyl halide should be a straight-chain alkyl halide with a halogen atom (e.g., bromine or iodine) at the position where the vinyl groups are added.

Step 4: For compound d, identify the alkyl halide precursor. The target structure suggests that the starting alkyl halide should be a branched alkyl halide with a halogen atom at the position where the vinyl groups are added.

Step 5: Write the general reaction mechanism. The lithium divinylcuprate reagent reacts with the alkyl halide via nucleophilic substitution, replacing the halogen atom with two vinyl groups. Ensure the correct stereochemistry and connectivity in the final product.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Alkyl Halides

Alkyl halides are organic compounds containing a carbon atom bonded to a halogen atom (F, Cl, Br, I). They are important in organic synthesis due to their reactivity, particularly in nucleophilic substitution and elimination reactions. Understanding the structure and reactivity of alkyl halides is crucial for predicting the products of reactions involving these compounds.

Lithium Divinylcuprate

Lithium divinylcuprate (Li2CuC4H4) is a reagent used in organic synthesis, particularly for the conjugate addition to α,β-unsaturated carbonyl compounds. It acts as a nucleophile, allowing for the formation of new carbon-carbon bonds. Recognizing how this reagent interacts with alkyl halides is essential for determining the appropriate starting materials for synthesizing target compounds.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group (such as a halide) by a nucleophile. These reactions can follow either an SN1 or SN2 mechanism, depending on the structure of the alkyl halide and the conditions of the reaction. Understanding these mechanisms is vital for predicting the outcome of reactions involving alkyl halides and reagents like lithium divinylcuprate.

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