For each reaction, draw the complete mechanism and the major organic product(s), paying attention to stereochemistry. (a) (b) OH LOH (еxcess) ? ? CH,Cl2 CH2CI2
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- Consider the reaction scheme shown below. HCI [1] ОН (a) Provide a detailed mechanism for reaction [1].4) Draw the complete electron-pushing arrow mechanism for the following reductions. Explain, using resonance contributors, the regiochemistry that results in each case. ỌMe Na, MeOH ? NH3 CHO Na, MeOH ? NH3a) Draw the mechanism, using good curved arrow notation, for the reaction of 2-methyl-2- butene with bromine in water, omitting any stereochemistry: b) (R)-3-butyn-2-ol is treated with 2 mol of HBr, yielding optically active Compound A (C4H8OBr2). Draw the structure of the reaction with the correct stereochemistry. c) Name Compound A above, including stereochemistry. d) Compound A is treated with HBr to yield Compound B (C4H7Br3). The resulting solution is optically inactive. Draw the product(s) obtained and explain why there is a loss in optical activity.
- Question 5. (20 points) Consider the following reaction. + PhLi (2 eq.) then water a) Propose a structure for the final product. b) Give a complete mechanism for the transformation. c) Draw an energy diagram of the transformation and briefly comment on the relative energies of the starting material, final product, and any intermediate(s), and about the rate determining step.Each heterolysis step on the left does not readily occur, but the corresponding one on the right does. Explain why. Hint: Draw the products of each heterolysis and determine the contributions to their driving force. (a) Br Br CH,CHOH CH;CH,OH (b) CH CHOH ? CH;CH,OH (c) you Br Br DMSO CH,CH,OH (d) CHCH,OH ? CH;CH,OHDraw the mechanism and product for each of (a) (b) NH2 the reactions shown. HS ? Acetone, H,O H,0
- When treated with NaOH, the bromide below gives an alkene by the E2 mechanism, by eliminationof the circled atoms: (a) Draw the Newman projection from which elimination takes place. (b) Draw the mechanism. (c) Draw the product with the proper stereochemistry. (d) Assign the proper stereochemical descriptor to the product. (Z, E? Trans,CiS?) (e)What would happen to the stereochemistry of the product if the enantiomer of the starting material were used inthe reaction?Draw the mechanism and predict the major product for each of the following reactions. (a) (b) O (c) NABH4 NABH4. 1. LIAIH4, Et,O ? CH;OH ? 2. H2SO4, H2O mOCH3 CH;OHFor the following dehydrohalogenation (E2) reaction, draw the major organic product(s), including stereochemistry CI (Cн Сок СH, HII (Cн, СОн
- N(CH2CH3)3 + HNO3 --------> a.) rewrite the reaction using bond-line structure of reagents and products of the reaction b.) supply the curved arrows explaining the mechanism of the reaction(4d) and PhMgBr, followed by reaction with the acid. Please draw that mechanism here! Even though benzoic acid is reformed as the product, a reaction does take place between benzoic acid 1. PhMgBr HO, 2. H30*Each of the following may participate in an elimination reaction, under the proper conditions. (a) Circle the alpha (a) carbon. (b) Circle the beta (B) carbon(s). (c) Draw the alkene product(s) that may form, with the new double bond between the a and ß positions. (d) If more than one alkene product is possible, circle the most stable (Zaitsev) product. A В J C K E F G 33-0
