4.1 What stereochemistry would you expect of the alkene obtained by E2 elimination of (1R,2R)-1,2-dibromo-1,2-diphenylethane? Draw the Newman projection of the reacting conformation and the structure of the alkene.
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- 6. Write the IUPAC name for the following compounds. Show the stereochemistry whenever required (a) HO NH2 CI (b) NH2 QH но (c) он Br H. (d) (e) OH Br BrWhich stereoisomer of 3-hexene forms (3S,4S)-4-bromo-3-hexanol and (3R,4R)-4-bromo-3-hexanol when it reacts with Br2 and H2O?(2R,3S)-2-Bromo-3-phenylbutane undergoes an E2 elimination when treated with sodium methoxide. Draw all possible Newman projections for the bond relevant for the elimination reaction, and use those Newman projections to explain the stereochemical outcome of the reaction. Draw the final product and provide its IUPAC name.
- What is the structure of (1S.2R)-1-ethyl-2-methyl-1,2-epoxycyclohexane? II OH IV(a) Rank the following carbocations in order of increasing electrophilicity (1 = lowest electrophilicity, 4 = highest electrophilicity). (b) Rank the following 1,1-halomethylcyclopentanes in order of reactivity in an SN1 reaction (1 = lowest reactivity, 4 = highest reactivity. CH3 CI B with SNI, nor reactive means more stable (c) Rank the following species in terms of increasing nucleophilicity in an SN2 reaction in a po aprotic solvent (1 = lowest nucleophilicity, 4 = highest nucleophilicity).A chemist allows some pure (2S,3R)-3-bromo-2,3-diphenylpentane to react with a solution of sodium ethoxide(NaOCH2 CH3) in ethanol. The products are two alkenes: A (cis-trans mixture) and B, a single pure isomer. Under the same conditions, the reaction of (2S,3S)-3-bromo-2,3-diphenylpentane gives two alkenes, A (cis-trans mixture) and C. Upon catalytic hydrogenation, all three of these alkenes (A, B, and C) give 2,3-diphenylpentane. Determine the structures of A, B, and C; give equations for their formation; and explain the stereospecificity of these reactions.
- 1. Draw the structure of all reactants and product for the following reactions. (a) 2-methyl-1-iodocyclopentane + NaOCH3 ------>A (b) A + (1) Hg(OAc)2, H2O/(2) NaBH4 ------>A chemist allows some pure (2S,3R)-3-bromo-2,3-diphenylpentane to react with a solution of sodium ethoxide(NaOCH2CH3) in ethanol. The products are two alkenes: A (cis-trans mixture) and B, a single pure isomer. Under thesame conditions, the reaction of (2S,3S)-3-bromo-2,3-diphenylpentane gives two alkenes, A (cis-trans mixture) and C.Upon catalytic hydrogenation, all three of these alkenes (A, B, and C) give 2,3-diphenylpentane. Determine the structuresof A, B, and C; give equations for their formation; and explain the stereospecificity of these reactions(a) Draw the major products A, B, and C for the Diels-Alder reactions below. A EtO2C. + В `CO̟Et
- 6. Provide the line structure of product E in the following reaction. Include stereochemistry for product E as indicated. No mechanism is required. C2 H20 CH,C2 Draw any enantiomer (Include stereochemistry)5. What product would you expect to obtain from the Sy2 reaction of (S)-2-bromo- hexane with sodium acetate, CH3CO2Na? Show the stereochemistry of both product and reactant.Q12. (1-bromoethyl)benzene 1 udergoes an elimination following an E1 mechanism. Fill in the following synthetic scheme by drawing the structure of intermediate 2 and product 3. The chemical formula of product 3 is provided as guidance. CH; RDS Br C3Hg E1 2 3