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- Perform retrosynthesis on the following molecule to break it into its original starting materials. In your work, you must include Diels-Alder reaction. .CI H. IZ5. Draw a detailed mechanism and give the products for the following Diels-Alder reaction. Label the Endo and Exo diastereomer. + ZON PhDetermine the mechanism of nucleophilic substitution of each reaction and draw the products, including stereochemistr CH₂CH3 CI Br + CN d. + CH3COOH a. acetone + -OCH3 e. DMF f. b. C. ||||| a ||||| Br H Br CH2CH2CH3 + CH3OH DMSO H CH3 CI Br + OCH₂CH3 + CH3CH₂OH
- 3.Help on Retro Synthesis from Diene to eudesmol by using Diels-alder. OTMS 3. YOH HO. H. a-eudesmola- 3. b. N OCH3 C. N Show the for reasonable Curved mechanism the reaction and make sure lone pairs + Conc HBr HBr 40c CN Br2. Determine the starting materials that could have been used to synthesize each of the Diels-Alder adducts shown below. Show stereochemistry when applicable. .CI H. .CI "CN
- 6. Determine whether the following reactions are SN1 or SN2. Draw the mechanism and the products with stereochemistry. a. b. Br Br + "CN + -OCH 3 acetone DMSO d. e. f. Br 11 + CH3OH + CH3CO₂H Dº Br + -OCH₂CH3 + CH3CH₂OH DMF 1, 2 of 2The following Walden cycle has been carried out. Explain the results, and indicate where Walden inversion occurs.Predict the product of this E2 elimination reaction. ||| Brill.... H3C Ph Ph H3C Ph Ph Ph CH3 || reaction H3C Ph IV CH3 NaOCH3 Ph H3C Bril... Ph CH3 Ph CH₂ Ph
- DBU Br DMSO, heat SN1 E1 SN2 E2 Strength of Nuc/Base Conc. Of Nu/Base Solvent Leaving group Reasoning:Select the approximate region where C-H aldehyde stretches typically occur in FTIR spectra (cm-1). a. 2200-2300 b. 3000- 3600 c. 2720; 2820 d. 100-500 e. 1650-1850 f. 1400-160034. Select the best synthetic sequence to accomplish the transformation shown. Br A. 1. NaOEt; 2. HBr, cold, dark; 3. H₂SO4, H₂O B. 1. NaOEt; 2. HBr hv, A; 3. KO/Bu C. 1. NaOEt; 2. HBr cold, dark; 3. KOtBu D. 1. NaOEt; 2. Br₂; 3. KOBU E. 1. NaOEt; 2. Br₂, hv 35. In the retrosynthesis shown below: which compound could be converted to the alkyne shown in a single reaction step, with the appropriate reagents? Br -Bri Br Br || ||| IV B. C. D. E. None 36. In the retrosynthesis shown below: which compound(s) could lead to the alcohol shown in a single step, with the appropriate reagents? OH IV I B. 11 C. ||| D. E. A. I & II 37. Which alkene cannot be converted into an alkyne by reacting it with 1) bromine followed by 2) an excess of sodium amide and then 3) water? || IV B. C. E. All work D. Br
