Hey, everyone and welcome back, identify the missing products. The starting material is benzene and in the first reaction, it reacts with propionyl chloride in the presence of aluminum chloride to produce product A and then product A produces product B using number one hydro and number two hydroxide in the presence of heat and one comma two ethane dial. OK. So let's think about the first reaction. If we have benzene and we use an acid chloride in the presence of aluminum chloride, we observe the friel crafts isolation. OK. So now what does that mean? It basically means that if we redraw the benzene ring and if we actually add our regent in its bond line representation, we will have our carbon group. Then on one side, we will have an ethyl group bo on the other side, we have chlorine. And then in the presence of aluminum chloride, we're going to generate an electro file which will undergo the electrolytic aromatic substitution. So we're going to replace one of the hydrogen atoms within the benzene ring with our carbonyl group. And specifically, we're going to form a ketone, we're going to form our carbon carbon bond removing our chloral group. And if we draw the final product, we're going to start with our carbon group. And on the other end, we're going to add the ethyl group. OK. So the free craft isolation essentially allows us to form the carbon carbon bond between the carbonyl group and one of the carbon atoms within the benzene ring. Well done. So now we have our key zone and we have to think about reaction number two, in which we are producing product B it states that number one, we're using hydro, right. So if we have two hydrogen atoms bonded to nitrogen, which is then bonded to another nitrogen, which has two hygienes bonded to it. In other words, we have two ngen atoms and four hygienes that's hydrogen. And number two, we are adding hydroxide heating the mixture and also adding one comma to ethane dial. This reaction is also known as the Wolf Kisner reaction or to be more specific, that's the Wolf Kushner reduction. So how does that work? We essentially have to remember that reduction in for carbo compounds in this case implies that we're going to remove our Carboni group. OK. So if we remove our Carboni group and replace it with two hydrogen atoms, we will be able to get an alky chain. So let's go ahead and do that. If we remove the Carboni group and draw a straight propylene, that would be it, we have replaced our carbon group. And instead of it. We now have two hydrogen atoms bonded to our carbon. So we have reduced our Carboni into an alkyl group. Well done. So let's label our products. We got our product A which is our song. Let's label that thing green. And then finally, we got our Alki benzene which is product B. Let's label that. And once again, let's review the stops. First of all, we're performing the craft satiation to get our Keats on. And in the second step of the reaction scheme, we're forming product B to get an alkyl benzene performing the Wolf Kisner reduction. That will be it. Thank you for watching and I hope to see you in the next video.

Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

21. Aldehydes and Ketones: Nucleophilic Addition

Wolff Kishner Reduction

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Wolff Kishner Reduction

Previous problem

5:05 minutes

Problem 85a

Textbook Question

Identify A–J:

Verified step by step guidance

Step 1: Analyze the first reaction. The starting material is benzene, and it reacts with CH3CH2CCl/AlCl3. This is a Friedel-Crafts acylation reaction, where the acyl group (CH3CH2CO-) is introduced onto the benzene ring. The product A will be an aromatic ketone.

Step 2: Examine the second reaction. Compound A reacts with hydrazine (H2NNH2) in the presence of a base (HO-) and heat (Δ). This is the Wolff-Kishner reduction, which converts the carbonyl group (C=O) in ketones to a methylene group (-CH2). The product B will be an alkylbenzene.

Step 3: Note the presence of ethylene glycol (HOCH2CH2OH) in the second step. Ethylene glycol is often used as a solvent or stabilizing agent in high-temperature reactions, but it does not directly participate in the Wolff-Kishner reduction.

Step 4: Summarize the transformations. Compound A is formed by the acylation of benzene, resulting in an aromatic ketone. Compound B is formed by the reduction of the ketone group in A to a methylene group, yielding an alkylbenzene.

Step 5: To identify A and B, consider the specific acyl group introduced in the first step (CH3CH2CO-) and the subsequent reduction of the ketone group. A is ethyl phenyl ketone (C6H5COCH2CH3), and B is ethylbenzene (C6H5CH2CH3).

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Key Concepts

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

Friedel-Crafts Acylation

Friedel-Crafts acylation is a key reaction in organic chemistry that introduces an acyl group into an aromatic ring. This reaction typically involves the use of an acyl chloride and a Lewis acid catalyst, such as AlCl3, to form an acylaromatic compound. The product, compound A in the diagram, retains the aromaticity of the benzene ring while adding a carbonyl functional group.

Wolff-Kishner Reduction

The Wolff-Kishner reduction is a method used to convert carbonyl compounds into alkanes by removing the oxygen functionality. This reaction employs hydrazine (H2NNH2) and a strong base, often under heat, to facilitate the reduction. In the provided diagram, the transformation from compound A to compound B illustrates this reduction process, resulting in the formation of an alkane.

Hydrazine and Base Reaction

Hydrazine (H2NNH2) acts as a reducing agent in organic reactions, particularly in the Wolff-Kishner reduction. When combined with a strong base, it promotes the conversion of carbonyl groups to hydrocarbons. The reaction typically requires heating to drive the elimination of nitrogen gas, leading to the formation of the final product, which is a diol in this case, as shown in the transformation from compound B.

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