Draw a curved arrow mechanism and predict a competing final product structure for each reaction sequence. Circle and label the appropriate structures "end of reaction #1" and "end of reaction # 2" in the mechanism. 1. Br₂, H₂O 2. NaH 3. H₂SO4. EtOH -OH (another stereoisomer of product would also form- draw it in the box at the right, but only show the mechanism leading to the stereoisomer above) (structure of the other product stereoisomer)
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- 5. Draw the mechanism that produces the major product for the following reactions. Do not draw minor products. Include resonance structures of the intermediates. Make sure you add all arrows! For both the reagents reacting together and resonance structures. Lone pairs must be shown on atoms that have charges. This includes the nitro group when drawn out. Arrows either start at electrons and end on at atom or start in the middle of a bond and end on the atom. 1) 2) CI NO₂ H₂N-CH3 (one major product) CI-CI3. Draw the major product in the following reaction and reaction mechanism. Remember when drawing a reaction mechanism, you need to show all nonbonding electron pairs, formal charges, electron flow arrows, and all resonance structures. What is the name of this mechanism? Determine and circle whether the substituent is an activator or deactivator. Explain what is meant by being an activator or deactivator and circle the single resonance structure that supports your decision regarding the substituent in the starting material. OH CH₂CH₂CH₂Br FeBr1. (10 points) Complete the reaction scheme below. Show all reagents and intermediates. No reaction is a possible answer. Do not neglect stereochemistry. NaCN DIBAL Br A "OCH3 (sodium cyanide)
- e 2. Draw the structures and explain why CH3CH₂O and CH3CO₂ are good nucleophiles but CH3SO3, water, and alcohols (R-OH) are poor nucleophiles. Propose a 'cutoff for the amount of negative charge needed to be a good nucleophile. CH3CH₂O CH3CO₂ CH3SO3 H₂O CH3OHCurved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. H Drawing Arrows H H H Ö :CHOHonor Gross ma's Rule. A) For this question draw a curved arrow mechanism, start converting the Start matenal to Product A Only you Make Sure Pairs, and heteroatoms. also show the relevant resonance- Structure, and the conservation of Charge & mass B.) Then explain why product A. is a good major product. Then explain Product B is the minor product is H₂CO why and AIC137 CY why at all. draw all lone H3CO 4.5 A + not observed HCO
- 3. A) Show all the unique mono-halogenated products for the reaction below. Circle the major product. Br₂ light B) Show the formal arrow pushing mechanism for the first and second propagation step which leads to the radical intermediate of the major product. Be sure to draw in the hydrogen which is being abstracted. Draw the products.1. Consider two SN1 reactions: (A) water and tert-butylbromide and, (B) water and 2- bromopropane, both having the same concentration of reactants. a. Draw the reactants (nucleophile and substrate) for both reactions (A & B). b. Draw a curved arrow mechanism for the reaction between water and tert-butylbromide (A). Show all reactants, intermediates, and products do not show transition state structures. c. Draw products of each reaction (A & B). d. Predict which reaction will be faster (A or B). - e. Draw an energy vs. reaction coordinate diagram showing only the rate-determining step for both reactions on the same set of axes (axes available on the next page). Draw the reaction (A) with a dotted line and (B) with a solid line, and assume that the potential energies of the reactants are the same in both reactions (i.e. the only difference is in the energies of the two different transition states and resulting intermediates).a. Fill in the mechanism below with curved-arrow electron pushing as well as necessary lone pairs of electrons and all formal charges. Note: Some atoms are only shown when relevant. b. Circle the rate determining step of the reaction.