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- d. 12. What is the simplest fused aromatic hydrocarbon? a. Naphthalene b. 1,2-Benzylpyrene c. Methylbenzene d. Cyclobenzene 13. In electrophilic aromatic substitution reactions, a phenyl substituent on the aromatic ring is a. a deactivator and a m-director b. a deactivator and an o,p-director c. an activator and an o,p-director d. none of the above 14. Acetylide ion formation requires a strong base like NaNH2 which in turn is made using ammonia and Na. The catalyst used in this reaction is a. Cu b. Fe C. Pt d. Pd 15. Hydroboration-Oxidation of terminal alkyne results in the formation of an a. Aldehyde by Markovnikov mechanism b. Ketone by anti-Markovnikov mechanism c. Enol by Markovnikov mechanism d. Aldehyde by anti-Markovnikov mechanism 16.p-Methoxybenzaldehyde can be prepared from anisole using the Gatterman- Koch formylation. What mixture of reagents is necessary for this process? a. CO, HCI, AICI3, CuCI b. CO, SO3, H2SO4 CO2, HCI, AICI3 d. CO2, SO3, H2SO4 e. CO2, HNO3, H2SO4 C.Show how the following compounds can be synthesized from benzene: a. m-chlorobenzenesulfonic acid d. 1-phenylpentane g. p-cresol b. m-chloroethylbenzene e. m-bromobenzoic acid h. benzyl alcohol c. m-bromobenzonitrile f. m-hydroxybenzoic acid i. benzylamineWhich of the provided schemes can be used to synthesize p-chlorophenol p-chlorophenol from benzen e? A. None of the below schemes are correct B. O C. D. SO3 H₂SO4 Cl₂ FeCl 903 H₂SO4 Product Product Product 1. NaOH 2. H₂O* SO 3 H₂SO4 Cl₂ FeCl Product Product Product Cl₂ FeCl H₂/Pd 1. NaOH 2. H₂O* p-Chlorophenol p-Chlorophenol p-Chlorophenol
- Which of the following is expected to be the MOST reactive towards electrophilic aromatic substitution? a. p-Cresol b. p-Toluidine c. p-Chlorophenol d.p-Chloroaniline 2. Which of the following is expected to be the LEAST reactive towards electrophilic aromatic substitution? a. p-Hydroxybenzoic acid b. p-Methoxybenzoic acid c. p-Aminophenyl acetate d. p-Methoxyphenyl acetateWhat is the best set of reagents to achieve deoxygenation of 2-pentanone to pentane? A. NaClO2/NaH2PO4 B. LiAlH4, Et2O C. DIBAL-H, THF D. NH2NH2/t-BuOK, DMSOa. Propose a mechanism for the reaction of acetic anhydride with water.b. How does this mechanism differ from the mechanism for the reaction of acetic anhydride with an alcohol?
- What products are obtained from the following reactions? a. ethyl benzoate + excess isopropanol + HCl b. phenyl acetate + excess ethanol + HClComplete the following reaction scheme. 1. DIBALH 2. H3O+ TMSCI Pyridine 1. LIAIH(t-BuO)3 SOCI2 2. H3O+ CrO3 H3O+Saponification with NaOH of this ester will result in which products? H.C Select one: O a. ethanoic acid + phenol O b. benzoic acid + ethanol O c. phenol acid + sodium ethanol O d. benzoic acid + sodium ethanol e. ethanol + sodium benzoate
- Select the reagent(s) necessary for the given step of these synthesis pathways: Reagents available a. f. PBr3 CH3CH2COCI b. C6H5 COCI c. AlCl3 g. Mg, ether h. H2SO4, conc d. NaBH4, ethanol i. SOCI₂ e. H2SO4, dil j. C6H5 CN Scheme 1: Step 7: Step 2: Scheme 2: MgBr CH3 H3C CH3 H3C Step 5: Step 3: CH3 2 OH OH CH3 3 HO-C-C-H Br CH3 CH2CH3 CH2CH3 MgCl 3 2 H3C CH3 CH3 H3C CH3 5 6 .OH H3C CH3 H₂C CH₂ H3C CH31. Give the product of the reaction of the cyclic anhydride shown below when treated with the following reagents. a. aquous NaOH b. aqueous HCI c. methanol d. sodium methoxide in methanol e. ethylamineB. Provide a reasonable mechanism for the non-enzymatic reaction below. :Ö NaOH / H₂O Ö: