The following reaction sequence was used in the synthesis of several derivatives of pros- taglandin C2. Analyze the structure using the chemistry you learned in this chapter and draw the structures of the synthetic intermediates A and B. 1. NANH, THF(solvent) NaCN A В 2. Br CI DMSO (racemic) (racemic) (racemic)
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- Give the products of the following reactions. CH3 (i) KMnO4, OH, A (ii) H₂O* CH3COOH + PC13 BrCH₂CH3 SAPY a.) b.) c.) (i) NaCN (ii) H3O+b) Optical isomers can often be formed during these reactions. For products A-H indicate how many different optical isomers you expect to form for each from these reactions (you do not have to indicate whether they are diastereomers/enantiomers). c) In the preparation of substance D by ozonolysis, the second step is necessary treatment of the reaction mixture with zinc in acetic acid. If we forgot this step, we would get substance V instead of substance D, which would probably explode when isolated. What is the structure of substance V? *24 X 1: ozone V e) What products do you expect to form if they react with alkene X: I - HBr in diethyl ether; II - Brl in methanol; III - PhSCI in diethyl ether; IV - Selectfluor in methanol. P M EtOH NA EtONa PhSNa EtOH E H+ O TsCl Pyridín F- T2, Pd/C G4 mCPBA H₂SO4 10 %, H₂O 1: BH3 H◄ 2: H₂O₂ ill X Br₂ cyclohexane HCI A > В B HBr warmth, benzoylperoxid 1: ozone 2: Zn, ACOH Mg THF с D D₂O K I + J NaOHPyrethroids are insecticides that target the nervous systems of insects. They have found widespread use because they have low toxicity to mammals and readily degrade in the environment. Consider the synthesis route of the following pyrethroid. X CCl₂ CCl4 Cl3C 2 eq. MeO a. Outline a probable mechanism for converting X to Y b. Suggest a reason for the regioselectivity of the formation of Y Z
- For the following reaction diagram the mechanism and draw the product 1. (CH,),CCI, AICI, 2. Cl,. AICI, 25. 26.Outline a scheme for the following synthesis. Show the reagents to be used for each step. Draw the products of each step. Do not diagram the mechanisms for any of the other steps.4. The anisole derivative below undergoes a selective cross coupling reaction on only one of the two bromides. Predict the structure of the product and explain why that is the mechanistically preferred product. OMe Pd°Ln, PhB(OH), (1 equiv) biaryl product Br K,PO,. THFM,0, 80 °c Br 5. A reaction proceeds with a 13:3 ratio of enantiomers. Convert this ratio to the percent enantiomeric excess (%ee).a) propose an outline of a possible mechanism for the conversion of a to b. provide illustrations as necessary. b) provide or suggest an explanation for the regioselectivity of "b" formation. x₂ CC13 CC14 Cl3C 2 eq. MeO- C
- 3 Draw the structure(s) of the major organic product(s) of the following reaction. 1. lithium diisopropylamide/hexane 2. 1 eq. CH3-CH=CH-CI • You do not have to consider stereochemistry. Omit products derived from the acidic or basic reagent itself, e.g. HN(i-Pr)2 derived from N(i-Pr)2. • If no reaction occurs, draw the organic starting material. • If substantial starting material is present at the end of the reaction, include it in the products. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom righ Separate structures with + signs from the drop-down menu. . . will ChemDoodle Y Jn [F 419. 20. Provide the major product of the following reaction sequence. Me Ph 1. Lithium dibenzylcuprate then workup 2. hydroxylamine, trace H+, heat major product (ignore stereochemistry Draw the structures of compounds X and Y in the scheme below Ph KCNTHC H₂O+, refluxNaproxen is an anti-inflammatory that is the active ingredient of Aleve. Choose the compound that would be suitable for preparing the necessary diastereomeric salts to purify the racemic mixture of naproxen shown below
- 2) a) Predict the reaction kinetics (E1/E2) for the following eliminations. Explain. b) Which reaction will provide a Zaitzev and which a Hofmann product? Specify the product. NaOH, A F NMes G H,SO, A 3) Why are the following substrates not practical for an elimination reaction? H,c CH, H,C K L2. Consider the following diagram: Br Он Suggest a suitable reagent(s) and intermediate to prepare the following carboxylic acid through a. Carboxylation of Grignard reagent b. Hydrolysis of cyanohydrin 3. Arrange the following pairs of compounds in order of increasing reactivity with a nucleophile. Explain your answers. a. and and NH2 CI b.1. Kindly answer the following questions below. You may use illustration to help explain your answers. a. sec-butyl alcohol remains optically active in aqueous base, but racemizes when mixed with dilute sulfuric acid. Suggest a mechanism accounting for this observation. b. The following 1935 experiment established that in SN2 reactions, a molecule undergoes an inversion of configuration. Optically active 2-iodooctane was reacted to with Na¹311 in acetone. It was observed that the rate of reaction depended on both [RI] and [I], but the rate of racemization was two times faster than isotopic exchange. Explain this set of results.. c. Explain the following observations: (i) why neomenthyl chloride and menthyl chloride yields the following products below; and, (ii) why menthyl chloride reacts 1/200 times as fast as neomenthyl chloride to yield the same product as neomenthyl chloride. 2022 a C/ neomenthyl chloride 2-menthene 25% 2-menthene 75% menthyl chloride 2-menthene only product