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- PQ-21. From the standpoint of reactivity, which is the poorest dienophile to react with 2,3-dimethyl-1,3-butadiene in a Diels-Alder reaction? H (A) CO2CH3 (B) (C) (D) CN(a) Draw the major products A, B, and C for the Diels-Alder reactions below. A EtO2C. + В `CO̟Et| Anthracene readily undergoes a Diels-Alder reaction with tetracyanoethene, even though anthracene is NC CN ? + aromatic. NC CN (a) Draw two possible products that can form from this reaction. (b) Explain why anthracene can readily undergo a Diels-Alder reaction, whereas benzene does not.
- 2,4-D is a synthetic auxin (a plant hormone) used in the control of broadleaf weeds, and one of the most widely used herbicides in the world. It is produced commercially by the following reaction: chloroacetic acid + dichlorophenol → hydrochloric acid + 2,4-D C2H3ClO2 + C6H4Cl2O → HCl + C8H6Cl2O3 How much chloroacetic acid does it take to manufacture 5.18 grams of 2,4-D?The following are several isomers of C10H14 with two fused six-membered rings. A B D E G H (a) Identify which will react with ethene in a Diels-Alder reaction and which will not. (b) Draw one more isomer with two fused six-membered rings that will react with ethene in a Diels-Alder reaction.) 1) Provide the structure of the major product, which results from Diels-Alder reaction. Draw the structure of the MOST stable product that results when the diene shown is treated with HBr at 80°C. HBr 80 °C CH3 Diels-Alder Reaction Provide the structure of the major organic product in the following reaction. XO
- 3. Predict the major product(s) for the following reaction. HCI o°c 4. Predict the product for the following Diels-Alder reaction. 5. Predict the product for the following Diels-Alder reaction. ÇOCH, AQ4. Discuss the reagents, conditions, and mechanism of the following reactions. a) Kolbe Reaction b) Williamson synthesis c) Reimer Tiemann reaction2) Predict the product for each Diels Alder reaction show below. Be certain to indicate stereochemistry as necessary. MeO گر S NC o=_ CN OEt A A
- What diene and dienophile are used in a Diels-Alder reaction to prepare the following compound? co,H COOH HOO and and COOH HOOC COO and and cook s HOOC IVUse arrows to predict the final favored product of the following Diels-Alder reaction. Use the step-wise mechanism to predict the final product of the following reaction. Show stereochemistry at stereogenic centers. NaBH4 CH;OH Use the step-wise mechanism to predict the product of the following reaction. (Excess) H.Provide the structures of compounds A-G and the reagent(s) R used to convert cyclohexene (1) to bromocyclohexane (2). A B Phs° 12 Br R 'Buo Os04 then H30° 2 1 D NH3/H2O ТСРВА E F H30° G