Draw the chemical structure for product (7) and provide a detailed (a) mechanism for the reaction [4] that explains the stereochemistry of product (8). (m-CPBA = meta-chloroperoxybenzoic acid) OH m-CPBA HCI C9H160 [4] (7) (8) [5] NAOH/H20 C9H1802
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- 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.Stereoisomers of α-bromocinnamic acid: draw the reaction mechiansim with arows for the dehydrobromination of 2,3-dibromo-3-phenylpropanoic acid with ethanol and KOH to produce (Z)-α-bromocinnamic acid and (E)-α-bromocinnamic acid. Also draw the transition state for The (Z)-isomer syn-periplanar transition state and anti-periplanar transition state of the (E)-isomer.Explain the E2 mechanism (bimolecular elimination) of of Elimination ?
- When the nitrogen-containing aromatic heterocyclic compounds 1 and 2 are treated with HCl, only 1 forms the hydrochloride salt, whereas compound 2 is unreactive. Provide an explanation for this observed reactivity.An optically active alkyne A (C10H14) can be catalytically hydrogenated to butylcyclohexane. Treatment of A with EtMgBr liberates no gas. Catalytic hydrogenation of A over Pd/C in the presence of quinoline poison and treatment of the product with O3 and then H2O2 gives an optically active tricarboxylic acid C8H12O6 (A tricarboxylic acids is a compound with three - CO2H groups.). Give the structure of A, and account for all observations.Plants extract are widely used in many parts of Cameroon to treat infectious disease or related symptoms including abdominal pains, itching, urinary and respiratory ailments, fever, coughing and diarrhea. Harunmadagascarin C as depicted below is an extract from the plant Harungana madagascariensis that has been studied for potential antimicrobial activity. Which statement best describes the stereochemistry of the compound? a. Harunmadagascarin C is achiral and does not have any stereogenic or chiral centers. b. The two stereogenic centers are currently in the E configuration, and the double bond in the ring structure is not stereogenic. c. There are four possible stereoisomers for Harunmadagascarin C since, as depicted, there are 2 stereocenters in the compound. d. There is one chiral center present in the molecule.
- Interestingly, reduction of the complex shown above mostly gives thealcohol enantiomer shown below after workup. a. Draw the other minor diastereomeric alcohol product. b. Briefly explain the diastereoselectivity of the reduction – why is oneenantiomer heavily favored? Draw a structure or structures to support youranswer.Arrange the structure on the image with regard to the reactivity towards nucleophilic acyl substitution 1 being the least and 3 being the mostAlthough two products (A and B) are possible when naphthalene undergoes electrophilic aromatic substitution, only A is formed. Draw resonance structures for the intermediate carbocation to explain why this is observed.
- Several steps in the synthesis of optically active duloxetine, anantidepressant sold under the trade name Cymbalta, are shown. Identifythe structure of intermediates A–C and the final product duloxetine,including stereochemistry, in this reaction sequence.In some nucleophilic substitutions under SN1 conditions, complete racemization does not occur and a small excess of one enantiomer ispresent. For example, treatment of optically pure 1-bromo-1phenylpropane with water forms 1-phenylpropan-1-ol. (a) Calculate how much of each enantiomer is present using the given optical rotation data. (b) Which product predominates—the product of inversion or the product of retention of configuration? (c) Suggest an explanation for this phenomenon.Epoxidation of the following allylic alcohol using the Sharpless reagent with (−)-DET gives two epoxy alcohols in a ratio of 87:13.a.Assign structures to the major and minor product. b.What is the enantiomeric excess in this reaction?