The last step in the synthesis of a series of potential anti- inflammatory agents is shown below (Ar is some arene ring. The reaction results in the loss of the elements of water (that is, the product has two less H's and one less O than the reagent shown). Give the structure of the product and the full, step-by-step mechanism for its formation. Ar Ar Cat. Na ome Me of
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- (b) Provide retrosynthetic steps leading to ketone 9 from bicyclic compound 8. Provide all intermediates (synthons) and their equivalents clearly labelled. No synthetic steps and mechanisms are required. 8-1 NC. 8 92. a) Provide the missing reaction product(s), or conditions to the following reactions. ACO + hv DCM, -55 °C NaOH (aq) C11 H1602a. Provide the structure of the hydrate of cyclopentanone. b. Provide the major organic product which results when pentanal is subjected to the following sequence of steps: 1. PhMgBr; 2. H3O+; 3. PCC.
- Suggest an efficient synthesis for the following transformation: .CI H. The synthesis above can be performed with some combination of the reagents listed below. Give the necessary reagents in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). KMNO4, A: NAOH, 1) BH3-THF G: 2) H2O2, D: HBr cold NaOH 1) O3; 2) В: DMS E: NaOMe conc. H2SO4, H: heat 1) Hg(OAc)2, C: HBr, ROOR F: H2/Pt H20 2) NABH4 I:12). Give the major product of the following reactions. (A) CH3 OCH3 (B) 1. H3O+ OH 2. SOCI₂ HO (C) CH3 CH3 3.(CH3)2CuLi (?) OH OCH3 CH3 (D) CI OCH 3 CH3 (E)The second part of the synthesis of 1 involves conversion from compound 5 to compound 8. N. TMSCN condition B reagent C Но- -N. N. BnO > 7 - H* H* "CN ОН Bno OBn 5 8 3a. TMSCN has the structure of (CH3)3 Si-CN and can be considered as an equivalent of cyanide ion, CN-. Deduce the structure of compound 6. 3b. Compound 6 is then converted to compound 8, via compound 7. Draw the structure of 7, condition B and reagent C.
- (c) Give the product for each of the following reactions. (i) 1. (CH3)2CULI A 2. H2О (ii) 1. (R)-CBS reagent Br B HO 2. Hао ČOOCH3 (ii) 1. CH3LI CH3 2. H20The Claisen condensation can be used as one step in the synthesis of ketones, as illustrated by this reaction sequence. 1. EtO Na+ 2. HCI, H₂O Draw the structures of each of the major organic products. • You do not have to consider stereochemistry. • Do not include counter-ions, e.g., Na*, I, in your answer. (a) compound a O * Sn [F compound a ? NaOH, H₂O Heat compound b HCI, H₂O Heat compound c (C₁1H22O)(c) Treating lactone B with two equivalents of phenylmagnesium bromide, followed by hydrolysis in aqueous acid, gives a compound with the molecular formula C18H22O2, as shown below. Propose a structural formula for this compound. 1. PhMgBr (2 eq.) 2. H'/H>O C18H2202 bj 1o 14 10I f6 40 & 3 4 00 (8)
- Provide all the missing products (A-C) and reagent (i). Suggest retrosynthetic analysis for this. 5. CO(OMe)e. NaH в. NaOMe, MeOH, A OMe TSOH toluene3. Suggest synthetic routes to achieve the products as shown below. a. b. 요。 OMe Hint: Knoevenagel reaction Hint: Wittig olefination OH OMe Hint: Julia olefinationChemistry 3. Complete the following reaction scheme. Give all product(s) and indicate major or minor and any relevant stereochemistry. (а) NaOEt heat (b) heat (c) Br NaCN DMF (d) (e) OH H,SO,/H,PO, heat (f) HBr (g) 1) BH. THE 2) H,0, OH (h) 1) Hg(OAC), H-0 2) NaBH, (i) KMNO, NaOH Cold