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- Consider the following nucleophilc substitution. LOCH3 Br OCH3 в A a. Identify the reaction conditions A and specify the reaction mechanism for the nucleophilic substitution. Explain your choice. b. Explain why the transformation does not give rise to significant elimination. c. Which product(s) B is formed in the reaction? Please specify the stereochemistry clearly with reference to the reaction mechanism.1. What product is expected to form in an Sy2reaction of OH¯with (R)-2-bromobutane? Show the stereochemistry of the reactant and the product. 2. What product is expected to form from the SN2reaction of 1-bromopentane with а. КОН? B. Nal? 3. What product would you expect to obtain from a nucleophilic substitution reaction of (S)-2- bromohexane with CH3CO,? Assume that inversion configuration occurs, and show the stereochemistry of both reactant and product? 4. Predict whether each of the following substitution reactions is likely t Sylor SN2. CI OAc CH3CO, Na+ CH3CO2H, H20 а. CH2BR CH2OAC CH3CO2- Na+ DMF b. OH HCI CI CH3OH с. CH3 CH3 Na+ SCH3 H2C=CH2B d. H2C=CCH,SCH3 CH3CN 5. Setting aside the double bond stereochemistry, what products would you expect from elimination reactions of the following alkyl halides? CH3 ÇI CH3 CH3CHCH2-C-CHCH3 ČH32. Consijder the reactiojn scheme below a. Draw the major product of this reaction. Show clearly (using wedge-and-dash lines) all stereoisomers formed under these reaction conditions. 1. BH3:THF 2. H2O2, NaOH b. What is the stereochemical relationship between the different stereoisomer products you drew in part 2a.?
- Which set of reagents is used for the Markovnikov addition of water to an alkene without rearrangement? A. BH3, THF followed by H₂O2, NaOH B. H₂O, H₂SO4 C. Hg(O₂CCH3)2, H₂O followed by NaBH4, NaOH D. none of theseWrite out the expected splitting pattern for hydrogens Ha, Hp and Hc 3Jab = 10 Hz На Hb 3Jpc = 7 Hz CI Hc Hc Ha:Hb:Hc: doublet, quartet, doublet Ha:Hb:Hc: quartet, quartet, triplet Ha:Hb:Hc: doublet, doublet of triplets, doublet Ha:Hb:Hc: doublet, triplet of doublets, doubleta. O-nitrochlorobenzene and o-nitrochlorobenzene undergo nucleophilic substitution rxn however m-nitrochlorobenzene does not. Explain this fact with a mechanism.
- Friedel–Crafts alkylation of benzene with (R)-2-chlorobutane and AlCl3 affords sec-butylbenzene.a. How many stereogenic centers are present in the product?b. Would you expect the product to exhibit optical activity? Explain, with reference to the mechanism.Which is the MAJOR product of the following reaction? Et 1) BH3:THF 2) H2O2, NaOH Which of the following best describes a key step in the mechanism for the reaction below? HO ... CH3 -CH3 dihydroxylation + en H3C- H3C- HO. electrophilic addition reaction to form a carbocation intermediate B nucleophilic attack by an alkene to form a cyclic (epoxide) intermediate elimination reaction by abstraction of a beta-hydrogen D free-radical substitution at the carbonyl carbon Which alkene will produce the HIGHEST yield of the alkyl halide below? Br. alkene HBr |Draw the major organic substitution product(s) for (2R,3S)-2-bromo-3-methylpentane reacting with the given nucleophile. İndicate the stereochemistry, including H's, at each stereogenic center. Omit any byproducts. Н Br CH3CH2O (conc.)
- For each of the following reactions, draw the major elimination product; if the product can exist as stereoisomers, indicate which stereoisomer is obtained in greater yield. a. (R)-2-bromohexane + high concentration of CH3O- b. (R)-3-bromo-3-methylhexane + CH3OH c. trans-1-chloro-2-methylcyclohexane + high concentration of CH3O- d. trans-1-chloro-3-methylcyclohexane + high concentration of CH3O- e. 3-bromo-3-methylpentane + high concentration of CH3CH2O- f. 3-bromo-3-methylpentane + CH3CH2OHFriedel-Crafts alkylation of benzene with (2R)-2-chlorobutane and AICI, affords sec-butylbenzene. a. How many stereogenic centers are present in the product? b. Would you expect the product to exhibit optical activity? Explain, with reference to the mechanism.Draw the major organic substitution product or products for (2R,3S)-2-bromo-3-methylpentane reacting with the given nucleophile. Clearly drawn the stereochemistry, including a wedged bond, a dashed bond and two in-plane bonds at each stereogenic center. Omit any byproducts. Br CH;CH20 (conc.) H.