✨ VIPSolutions

Let's analyze each compound for retrosynthesis and propose start materials and key steps for their synthesis: --- ### 1. **Compound 1** (Cyclohexanone with a fused aromatic ring) #### Retrosynthetic Analysis This is **1-tetralone** (1,2,3,4-tetrahydronaphthalen-1-one). **Retrosynthesis:** - This compound can be synthesized by a Friedel-Crafts acylation. **Start materials:** - Benzene (aromatic ring) - Succinic anhydride (provides the 4-carbon chain for the cyclohexanone ring) #### Mechanism (Summary): 1. **Friedel-Crafts Acylation:** Benzene reacts with succinic anhydride in the presence of AlCl₃ to form 4-phenylbutanoic acid. 2. **Cyclization:** The acid is cyclized (by heating with polyphosphoric acid or another dehydrating agent) to form 1-tetralone. --- ### 2. **Compound 2** (Alkene between benzene and phenyl groups) #### Retrosynthetic Analysis: This is **stilbene** (1,2-diphenylethene). **Retrosynthesis:** - This compound can be synthesized by the **Wittig reaction** or **Aldol condensation**. **Start materials:** - Benzaldehyde (C₆H₅CHO) - Benzyltriphenylphosphonium ylide (for Wittig), or - Acetophenone and benzaldehyde (for Aldol) #### Mechanism (Summary using Wittig reaction): 1. **Formation of ylide:** Benzyl bromide reacts with triphenylphosphine to form the ylide. 2. **Wittig reaction:** The ylide reacts with benzaldehyde to form stilbene. --- ### 3. **Compound 3** (Benzylideneacetophenone) #### Retrosynthetic Analysis: This is **chalcone** (1,3-diphenyl-2-propen-1-one). **Retrosynthesis:** - This compound is commonly synthesized via an **Aldol condensation**. **Start materials:** - Benzaldehyde (C₆H₅CHO) - Acetophenone (C₆H₅COCH₃) #### Mechanism (Summary): 1. **Aldol condensation:** Acetophenone reacts with benzaldehyde in the presence of a base (NaOH) to form chalcone via an enolate intermediate. --- ## Summary Table | Compound | Name | Start Materials | Key Reaction | |----------|--------------|------------------------|---------------------------| | 1 | 1-Tetralone | Benzene, Succinic anhydride | Friedel-Crafts acylation, cyclization | | 2 | Stilbene | Benzaldehyde, Benzyltriphenylphosphonium ylide | Wittig reaction | | 3 | Chalcone | Benzaldehyde, Acetophenone | Aldol condensation | --- Would you like to see the detailed step-by-step mechanisms for each?

Certainly! Below are the structures for each compound along with their start materials: --- ### 1. **1-Tetralone (Compound 1)** **Structure:** A fused ring system with a cyclohexanone fused to a benzene ring. **Representation:** ``` ________ / \ | | | | \ / \______/ || C=O ``` *(Cyclohexanone fused to benzene, representing 1-tetralone)* **Start Materials:** - Benzene - Succinic anhydride --- ### 2. **Stilbene (Compound 2)** **Structure:** ``` Ph—CH=CH—Ph ``` *(Two phenyl rings connected by a double bond)* **Representation:** ``` C6H5—CH=CH—C6H5 ``` **Start Materials:** - Benzaldehyde - Benzyltriphenylphosphonium ylide --- ### 3. **Chalcone (Compound 3)** **Structure:** ``` Ph—CH=CH—C(=O)—Ph ``` *(A conjugated enone with two phenyl rings)* **Representation:** ``` C6H5—CH=CH—C(=O)—C6H5 ``` **Start Materials:** - Benzaldehyde - Acetophenone --- If you'd like, I can also provide the detailed step-by-step mechanisms or drawings for each synthesis!