The compound A can give potentially three products of intramolecular alkylation (three different regioisomers not stereosiomers). Give structure of each. In reality, only one is formed. Show which one and explain briefly why. MeOOC Br HH A KHMDS THF, -78 °C
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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 Coldhe following alkene undergoes hydroboration-oxidation to yield a single product rather than a mixture. Explain the result, and draw the product show- ing its stereochemistry. 8.25 From what alkene was the following 1,2-diol made, and what method was used, epoxide hydrolysis or OsO4? 8.26 Predict the products of the following reactions (the aromatic ring is unreactive in all cases). Indicate regiochemistry when relevant. H₂/Pd H or (a) (b) (c) (d) (e) (f) Br₂ Os04 NMO Cl₂, H₂O CH₂I₂, Zn/Cu meta-Chloroperoxy- benzoic acid ? ? ? ? ? ?7B. (2 reactions (should clearly indicate the stereochemistry). Draw the structure of the product, substrate or condition in the following (a) ОН (b) Ме 1) OsO4 2) NaHSO3 (c) 1) (sia)2BH 2) NaOH/H2O2 H20
- Give the detailed mechanism for the following nitration reaction. Show the contributing resonance structures and the resonance hybrid for the intermediates. HNO,, H,SO, NO2Compound 1 has been shown to be a useful precursor in the synthesis of natural products. (Org. Lett. 2004, 6, 4439-4442). In principle, four stereoisomers are possible when this compound is subjected to catalytic hydrogenation. Draw these stereoisomers and describe their relationships. HO O OH H₂ - ? Pt Modify the four structures below, as necessary, to draw the four stereoisomers that are possible from catalytic hydrogenation of compound 1. Use the single bond tool to interconvert between double and single bonds.Friedel–Crafts alkylation of benzene with (R)-2-chlorobutane and AlCl3 affords sec-butylbenzene. Would you expect the product to exhibit optical activity? Explain, with reference to the mechanism.
- 3. following reactions. (a) Draw the product(s) including its(their) stereochemistry in each of the H20 (6) Br cI :8=c-H (i) 1. SOCI, OH 2. CH300 HBr (aq.) (iv) (b) Draw a stepwise mechanism for the formation of products in the reaction below. OH Br (c) Device a synthesis of the product from the given starting material for the following transformation. More than one step is required. ÇI HO.This reaction is also an important reaction of the tricarboxylic acid cycle in cells, wherein the reaction occurs in neutral solution, so the acid groups are both ionized to the carboxylate form. The reaction is catalyzed by the stereospecific enzyme fumarase that utilizes only the trans form of 2-butenedioate ion (also known as fumarate) and produces only the (S)-2-hydroxysuccinate enantiomer (also known as (S)-malate). Draw the correct stereochemical structures of these two compounds of the fumarase-catalyzed reaction. Be sure to include all hydrogen atoms and show the carboxylates as anions.The compound to the right was treated under the following two conditions. Give the major product(s) of each reaction. If applicable, assume rearrangements will Br осcur. a) Left at 25°C overnight in ethanol b) Refluxed in boiling ethanol overnight
- Complete the following reaction scheme. Give all product(s) and indicate major or minor and any relevant stereochemistry (d) dil HCl (e) ОН Conc H2SO4 heat (f) HBrThe following Diels-Alder reaction product is an intermediate in the synthesis of cholesterol. Provide the structure of the major product. Show stereochemistry when applicable. Hint: there are two possible dienophiles, which one is the better dienophile? Provide a brief explanation of your choice. CH,O.Complete the Reaction below and provide the following (i) a detailed stepwise mechanism to account for the product(s), including all steps involved (ii) Clearly show all the resonance structures and intermediates formed leading to the product. H₂NCH3, H (cat.)