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- Chemistry 3. Complete the following reaction scheme. Give all product(s) and indicate major or minor and any relevant stereochemistry. (а) NaOEt heat (b) heat (c) Br NaCN DMF (d) (e) OH H,SO,/H,PO, heat (f) HBr (g) 1) BH. THE 2) H,0, OH (h) 1) Hg(OAC), H-0 2) NaBH, (i) KMNO, NaOH ColdQ.1 Identify the structure of the products A and B in the following reactions with correct stereochemistry. Provide a suitable justification for the observed stereochemistry. OR LIAIH, LIAIHA B When When R = CH,Ph R= TBDMSQ.4 Identify the structures of A and B from the following reaction. Provide a suitable justification or the formation of these products/- NNHTS NNHTS NABD, NaBH, A B CH;CO,H CH,CO,D ind
- Draw the structure of (S,S)-ethambutol, a drug used to treat tuberculosisthat is 10 times more potent than any of its other stereoisomers. (See attached)(a) What orbitals are used to form the indicated bonds in α-sinensal?(b) In what type of orbitals do the lone pairs on O reside?Alkenes can be converted to alcohols by hydroboration-oxidation. (a) Draw the structure of the alcohol or alcohols formed in the reaction sequence. Clearly indicate stereochemistry by drawing a wedged bond, a dashed bond and two O Hint in-plane bonds per each chiral carbon. Draw hydrogen atoms that are connected to wedge-and-dash bonds.(b) Characterize the product or products of the reactions. The first step of the reaction, hydroboration, involves addition of BH, to the double bond, with -BH, attached to one carbon and hydrogen Be sure to draw hydrogens on oxygen, where applicable. attached to the other. Consider both Rings the regioselectivity and the Select Draw More Erase stereochemistry of this addition. H Diborane, B,H,, is a source of borane, BH,, and can be used 1. B2H6, interchangeably. Diglyme is a solvent. diglyme 2. H2О2, НО", The product or products of the reaction are characterized as being O S. O racemic. O achiral. O R,S (and/or S,R). O R. O S,S. O R.R. O diastereomers.
- Give the major organic product(s) of the following. Include stereochemistry when applicable. 1) Nal Br a) 2) NACN, acetone I) NAOC(CH,),, heat b) Br 2) BH; THF; 3) H,O,. NaOH(aq) 1) HCI 2) KOCICH,), heat 1) NAOH, heat Br 2) МСРВА 1) KOC(CH,), heat Br e) 2) H,0"The pk, of phenol (C,H5OH) is 10.0. When a methyl (CH3) group is attached to the ring, the pK, increases, as shown here for the ortho, meta, and para isomers. OH ОН ОН ОН CH3 (a) Explain why the pk, values of all three isomers are higher than the pk, of phenol itself. (b) Explain why the meta isomer has the lowest pk, of CH3 Phenol CH3 the three isomers. pKa = 10.0 10.3 10.1 10.2The bicyclic heterocycles quinoline and indole undergo electrophilic aromatic substitution to give the products shown.(a) Explain why electrophilic substitution occurs on the ring without theN atom for quinoline, but occurs on the ring with the N atom in indole. (b)Explain why electrophilic substitution occurs more readily at C8 than C7in quinoline. (c) Explain why electrophilic substitution occurs morereadily at C3 rather than C2 of indole.
- VI. Carbonyl compounds9. Which of the following chiral ketones undergo racemization in the presence of a strong base? Draw all enolforms and interpret! Determine the absolute configuration of the chiral centers!(a) Provide the missing reagents and line structures of the products (C- E) for the following reactions. Include stereochemistry for products Cand E as indicated. No mechanisms are required. (5) C H,0 Show stereochemistry any one diastereomer OH PCC. CH;Cla D H. Pd/C Show stereochemistry any one enantlomerOrg. Chem. 1. EA26. Can you please draw out all four , and explain what a stereoisomer is in relation ? Thanks