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- 1. Write the structure of the aminal or hemiaminal intermediate and the imine product formed in the reaction of Acetaldehyde and benzylamine, C6HSCH2NH2. 2. Write the structure of the hemiaminal intermediate and the enamine product formed in the reaction of 3-Pentanone and pyrrolidine. 3. Identify the alkene formed in the following reaction 'H. (CeHs)»P- 4. Predict the principal organic product for the following reaction. K2Cr2O7 H2SO4, H20 H. 5. What is the expected chemical shift for the aldehyde hydrogen in 'H NMR and aldehyde carbon in 13C NMR?12.Use of KMnO, to effect oxidative cleave of the alkene J, C3H16, yields two fragments, one of which is butanoic acid and the other a ketone, Q. When J reacts with one molar equivalent of H-Cl, the alkyl halide K, C3H17CI, is formed. What are the structures of J, J, and Q? Write all the reactions, and show your reasoning.We have a hydrocarbon, C16H26. The compound has two triple bonds and the acids produced by ozonolysis are CH3(CH2)4CO2H and H2OCCH2CO2H. What is a likely structure for this hydrocarbon?
- 5. An unknown hydrocarbon A with the formula CóH12 reacts with 1 molar equivalent of H2 over a palladium catalyst. Hydrocarbon A also reacts with OsO4 to give diol B. When oxidized with KMNO4 in acidic solution, A gives two fragments. One fragment is propanoic acid, CH3CH2CO2H, and the other fragment is ketone C. What are the structures of A, B, and C? Write all reactions and show your reasoning.Give the major organic product(s) for the following reaction Br₂ (1 mole) ? room temperatureDraw the structure of the major organic product(s) of the reaction. (CH3CH₂)2CuLi CI ether, -78° C • You do not have to consider stereochemistry. • Draw one structure per sketcher. Add additional sketchers using Separate multiple products using the + sign from the drop-dow 2-85 // ? ChemDoodle n[F >
- Some alcohols undergo rearrangement or other unwanted side reactions when they dehydrate in acid. Alcohols may be dehydrated under mildly basic conditions using phosphorus oxychloride (POCl3) in pyridine. The alcohol reacts with phosphorus oxychloride much like it reacts with tosyl chloride, displacing a chloride ion from phosphorus to give an alkyl dichlorophosphate ester. The dichlorophosphate group is an outstanding leaving group. Pyridine reacts as a base with the dichlorophosphate ester to give an E2 elimination. Propose a mechanism for the dehydration of cyclohexanol by POCl3 in pyridine.Specialized reagents and their acronyms: MCPBA= meta-chloroperbenzoic acid; HOAC = acetic acid, NaOAc = Sodium Acetate; Ph= phenyl = C6H5-; P(Ph)3 = triphenyl phosphine; NBS = N- bromosuccinimide, PBR3, SOCI2, AlCl3, FeBr3, H2SO4, Li, Na, Mg, Br2, CrO3, LDA = lithium diisopropylamide, PCC = pyridinium chlorochromate, KO-C(CH3)3, LAH = LIAIH4, (sia)2BH = disecondary isobutyl borane, KMNO4, HIO4 = periodic acid %3D %3D %3D %3D %3D write the missing reagents and solvents over the arrows. Some transformation require multiple steps. In some cases there will be multiple arrows. Br BrIt contains a vinyl group attached to benzene. Imagine it reacting with KMNO4 in acidic medium. What is/are the product(s)? A 1-phenylethane-1,2-diol B 2 moles of carbon dioxide C Carbon dioxide and benzoic acid D Carbon dioxide and benzaldehyde
- Specialized reagents and their acronyms: MCPBA= meta-chloroperbenzoic acid; HOAC = acetic acid, NaOAc = Sodium Acetate; Ph= phenyl = C6H5-; P(Ph)3 = triphenyl phosphine; NBS = N- bromosuccinimide, PBR3, SOCI2, AICI3, FeBr3, H2SO4, Li, Na, Mg, Br2, CrO3, LDA = lithium diisopropylamide, PCC = pyridinium chlorochromate, KO-C(CH3)3, LAH = LIAIH4, (sia)2BH = disecondary isobutyl borane, KMNO4, HIO4 = periodic acid %3D write the missing reagents and solvents over the arrows. Some transformation require multiple steps. In some cases there will be multiple arrows. Ph -Ph Ph Ph Br22. Calculate the percent atom economy for the following hydroboration-oxidation reaction. This is another method of hydration of an alkene. Be careful with stoichiometry! You must multiply molecular weights by their stoichiometric coefficients. ОН 3 3 + BH3 +Na;BO3 + 3 H20 +3 H2O2 +3 NaOHSpecialized reagents and their acronyms: MCPBA= meta-chloroperbenzoic acid; HOAC = acetic acid, NaOAc = Sodium Acetate; Ph= phenyl = C6H5-; P(Ph)3 = triphenyl phosphine; NBS = N- bromosuccinimide, PBr3, SOCI2, AICI3, FeBr3, H2SO4, Li, Na, Mg, Br2, CrO3, LDA = lithium diisopropylamide, PCC = pyridinium chlorochromate, KO-C(CH3)3, LAH = LIAIH4, (sia)2BH = disecondary isobutyl borane, KMNO4, HIO4 = periodic acid %3D %3D %3D %3D %3D write the missing reagents and solvents over the arrows. Some transformation require multiple steps. In some cases there will be multiple arrows. Ph CH CH o 0om ilubongo CEC-Ph In questions 14-24, write the products of the following transformations. If there is no reaction write NR. Indicate R or S or racemic or indicate cis or trans where appropriate OH + LDA THF solvent (S) Ph