The last part of the synthesis is to assemble moieties 8 and 11a together. N. НО HN P-O HCI (aq) 12 11 a "CN "CN HƠ он 1 8 5a. During the formation of compound 12, an inversion of stereochemistry has occurred. Note that 11a is a single stereoisomer of 11.
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- asapb) 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 NaOH7. Give the stereochemistry for the product of each step of the conversion of trans-4-t- butylcyclohexanol to its cis isomer by the following reaction sequence. a. Reaction of the trans isomer with p-toluene sulfonylchloride in pyridine to compound A (C17H2603S). b. Reaction of A with sodium benzoate in dimethylformamidewith heat to compound B (C17H1402). c. Reaction of B with an aqueous solution of sodium hydroxide to give the cis isomer of the original starting material.
- Pyrethroids 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 Z3. Provide the products for the following reactions. Provide the correct stereochemistry where necessary. HBr 1.) NaBr / DMSO 2.) H₂O excess HI7. An unknown amine X has the molecular formula C8H₁7N. Treatment of amine X with excess CH31 followed by Ag₂O and heat afford only a mixture of two isomeric unknown amines Y and Z, each with the molecular formula C9H19N (indicating one DUS). Treatment of the mixture of Y and Z with excess CH3l, Ag₂O and heat afforded the following dienes along with N(CH3)3: Unknown amine X has only four peaks in its 1³C NMR spectrum and no peaks greater than 3000 cm-1 in its IR spectrum. What are the structures of X, Y and Z?
- Discuss the following nucleophilic substitutions in terms of reaction conditions and stereochemical output. RO. NaCN Br R= H, CH3 Identify the preferred substitution mechanism for the following reactions. CH3 RSH ROH R. X = CI, Br, I R= H, CGH51. Give the structures of the products obtained when the following are heated. Include stereochemistry where relevant. A B C NEC CEN + + + NO₂ NO₂ 2. Which compounds would you heat together in order to synthesize the following?Give the products of the following reactions. CH3 (i) KMnO4, OH, A a.) (ii) H₂O* b.) CH3COOH + PC13 c.) BrCH₂CH3 (i) NaCN (ii) H3O+
- 7. Complete the following equations giving the structures for the products. Be sure to indicate the appropriate stereochemistry. If no reaction occurs write N.R. + PCC h) OH KMnO 1) Yo -OH - o + HBr BH, THF RO-OR peroxide O-OH peroxy acid H₂O₂, NaOH4. The Jones oxidation reaction has two basic parts: addition of chromic acid onto the alcohol (step 1) then reaction of the chromate ester to form a carbonyl (step 2). lorisoo |3| Cr-OH 0 НО HO-Cr-OH - + H2О :Cr-OH ОН (Cr+6) (Cr+4) a. Give the curved arrow mechanism for step 2 (reaction of the chromate ester) in this reaction. CH O HOH b. Is carbon oxidized in step 1 or step 2? How can you tell?Possible alternative brominations include: Veratrole (1,2-dimethoxybenzene) to 1,2-dibromo-4,5-dimethoxybenzene; 4-Methylacetanilide to 2-bromo-4-methylacetanilide; 2-Methylacetanilide (made in experiment S.1) to 4-bromo-2-methylacetanilide; Vanillin to 5-bromovanillin; Acetanilide to 4-bromoacetanilide; a. b. C. d. e. EXPERIMENT S4: BROMINATION OF AROMATIC COMPOUNDS Certain other acetanilides made in experiment S.1 may also be used as precursors in this experiment. Estimated time: 1 afternoon Associated learning goals: Section 6, LG 6.6; Section 7, LG 7.2 and 7.4 Pre-lab report: complete the standard report form, and answer the following questions. In this experiment, molecular bromine (Br2) is generated from the redox reaction of potassium bromate with hydrobromic acid. Write a balanced equation for this process. Briefly outline the mechanism by which Br2 brominates your aromatic compound. Why do the bromine atoms end up at the positions indicated rather than anywhere else in the…