2. Predict the major product of each reaction. Make sure to indicate the relative stereochemistry at each site of hydrogenation, if applicable. (a) D2 RHCI(PPh)3 cat. (b) H2 [(COD)Ir(PCY3)(py)[PF] cat. (c) H2 RHCI(PPH3)3 cat. "OBz (d) OH O H2 [Rh(NBD)(dppb)][PF] cat.
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- 1. Two Rh(1)-phosphine catalysts for olefin hydrogenation, Wilkinson's catalyst and a Schrock-Osborn catalyst, are shown below. They are known to operate by different mechanisms. Ph2 PF6 PPH3 Ph,P., Rh PPH3 CI Ph2 Wilkinson Schrock-Osborn 5-hexene-2-one (a) For each catalyst, give the mechanism for hydrogenation of 5-hexene-2-one. Please name each elementary step (e.g. oxidative addition, migratory insertion, dissociation, etc.). (b) Discuss several factors that contribute to the catalysts operating by different mechanisms. DELLWhich conditions will cause the interconversion shown? how? H H2/ Lindlar catalyst oa. Li/ NH3lia) ob. H2 / PtO2 (1) Brg: (2) KOH / E:OH od. (1) Hg(OAc)2 / THF / H2O: (2) NaBH4 е.Which conditions will produce the target product in the highest yield? O A) 1. BH3; 2. H₂O₂, NaOH, H₂O B) 1. OsO; 2. S(CH3)2 C) 1. Hg(OAc)₂, H₂O; 2. NaBH4 D) H₂SO4, H₂O A ? B OH racemic mixture
- Identify the major product of the reaction of an alkene shown below. ||| 1. Hg(OAc)2, H2O 2. NaBH4, NaOH ....... ОН || IV ОН о, ОН.0. For 0.1 M equimolar reaction of CH3COOH + NH3 ----> CH3-CO-O™ + NH4+ How does the concentration of ]? [CH3COOH] compare to that of [CH3-CO-O (a) Equal (b) Greater than (c) Less than) (d) not possible determine a9. What is the major organic product generated in the reaction sequence below? CI ďa (A) (B) -CI Br 1. K OtBu 2. Cl₂ (C) O ICI ㅎ........ (D)
- j. 1,2-epoxybutane + acid in methanol Reaction Type(s) Mechanism(s) Product(s). Stereochemistry (if applicable) k. (R)-3-methylbutan-2-ol + TsCl + pyridine in DMSO Reaction Type(s) Mechanism(s) Product(s)_ Stereochemistry (if applicable)7. Reaction Scheme. NH₂ NH2 or two differnet methods (no same steps/reagents) C5H12N2 1. xs Mel, xs K2CO3 2. Ag2O, H₂O 3. heat Br2, xs NaOH, xs H₂O OHC 1.03 2. DMS CHOWhich synthetic route(s) would complete the reaction shown? Br || ||| I and II O I and III ? HO OH + enantiomer Synthesis I: 1. NaCCCH3; 2. Na/NH3(I) ;3. OsO4; 4. NaHSO3, H₂O Synthesis II: 2. NaCCCH3; 2. H2, Lindlar's catalyst; 3. MCPBA; 4. aq. H₂SO4 Synthesis III: 1. NaCCCH3; 2. H₂, Pt; 3. MCPBA; 4. aq. H₂SO4
- 2. Complete the following reaction wheel providing structures or reagents where needed. Show stereochemistry where necessary. d e j 1). BH3.THF 2). H₂O₂, OH* 1). Na 2). CH3CH₂Br 1). CH3MgBr 2). H3O+ a 2). H3O+ с j 1 k 1). CH3CH₂MgBr CrO3, H+ TSCI Pyridine 1. Br₂, H₂O h Mal H*/heat OHDraw the structure of the expected major organic product for each of the following five (5) questions. Specify stereochemistry clearly, if relevant. А. H3C. HBr ČH3 В. H3C, a.) BH3 THF b.) excess H,02 CH3 aq. NaOH NaCN H3C CH3 Br D. 2 Li Br E. a.) H3C, product 1D b.) dil. aq. HCI C.4. For the following reactions, develop a transition-state structure using molecular models which would account for the observed stereoselectivity. Also, describe the type of pericyclic reactions using the proper terminology. (each Br heat A & Br b) F 0°C F heat heat d) product? =& & MeO₂C OCH3 H HO 1. CO₂Me مر CO₂Me LOCH3 heat heat MeO₂C HO