6. Complete the mechanism for each by adding arrows and charges where required. Hint: 1. Add H* to form most stable carbocation. Will it rearrange? 2. Nucleophilic attack of carbocation by anion. Refer to your notes. Br HBr Н-Br Br product HСІ CI- Н-СІ CI add H* add (+), then add (+), then product rearrange attack
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- ited Draw both resonance structures of the most stable carbocation intermediate in the reaction shown. od m... • You do not have to consider stereochemistry. . Do not include anionic counter-ions, e.g., I', in your answer. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom Separate resonance structures using the → symbol from the drop-down menu. ● CH4 + ? HBr1.) Draw the least stable resonance form for the intermediate in the following electrophilic substitution reaction. N N Br₂/FeBr3 • You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. • In cases where there is more than one answer, just draw one. [Review topics] 2.) Draw the most stable resonance form for the intermediate in the following electrophilic substitution reaction. [References OH OH Br₂ You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. • In cases where there is more than one answer, just draw one. Br 'BrIn Part 1 add the curved arrows to the nucleophilic acyl substitution reaction mechanism. In Part 2, answer the multiple-choice question about the reaction in Part 1. Part 1 See Periodic Table O See Hint :ö: :Br: Add the missing curved arrow notation. 20 F CI Br I Part 2 Which statement is most correct regarding the equilibrium for the above reaction? Choose one: O The equilibrium favors the right (i.e., Kea > 1) because acetate is a better leaving group than bromide. O The equilibrium favors the right (i.e., Keg > 1) because bromide is a better leaving group than acetate. O The equilibrium favors the left (i.e. Keg « 1) because acetate is a better leaving group than bromide. O The equilibrium favors the left (i.e., Keg« 1) because bromide is a better leaving group than acetate.
- The carbocation intermediate formed in the first step is resonance-stabilized. Draw the other resonance structure (by modifying the provided drawing) and add curved arrow(s) to convert the first resonance structure into the second one. Use the +/- tools to add/remove charges, and use the single bond tool to interconvert between double and single bonds. ÇH3 CH3 H3C. H,C. CH3 CH3 ČH3 ČH3 ČH3 ČH3 Edit Drawing2. The intermediate in the following nucleophilic aromatic substitution reaction has at least 5 resonance structures. For this question, complete the following tasks: a. Show the mechanistic arrow(s) for the first step. b. Draw TWO of the many resonance structures of the intermediate, drawing out the -NO₂ groups in each. c. Draw the neutral product. يمهم NO₂ NO₂ HO and others neutral product4. Circle the electrophilic and nucleophilic atoms in each substitution reaction below. Provide the neutral organic product; where a stereocenter is created, use a wavy bond to indicate a mixture of configurations or wedges/dashes for stereospecific reactions. Also, provide the dominant reaction mechanism (Sn2 or SN1) somewhere in each box. A. Br NaSEt DMF В. ELOH C. .SO2NHNA Cl + D. NaH Br- HO, DMF
- 4. Complete the phrases with one or more of the following terms: SNI, SN2, E1, E2. a) The reaction takes place in two or more steps. b) The reaction goes through a carbocation. c) The rate determining step has two reactants. d) The rate is independent of the concentration of nucleophile or base. e) Zaitsev's rule is often applicable to the products..2. CI The intermediate in the following nucleophilic aromatic substitution reaction has at least 5 resonance structures. For this question, complete the following tasks: a. Show the mechanistic arrow(s) for the first step. b. Draw TWO of the many resonance structures of the intermediate, drawing out the -NO₂ groups in each. c. Draw the neutral product. NO₂ NO₂ HO and others neutral productDraw both resonance structures of the most stable carbocation intermediate in the reaction shown HCI - You do not have to consider stereochemistry. -Do not include anionic counter-1ons, e.g., I, in your answer. - Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. - Separate resonance structures using the symbol from the drop-down menu. y自ノ ee P. opy aste [F CH
- Draw both resonance structures of the most stable carbocation intermediate in the reaction shown. + HCI You do not have to consider stereochemistry. • Do not include anionic counter-ions, e.g., I, in your answer. • • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right Separate resonance structures using the symbol from the drop-down menu. ← - CHA ? n ChemDoodleFor the reduction of 2-methyl cyclohexanone to methyl cyclohexanol using NaBH4... 1. What is the reaction mechanism (draw curved arrows)? What is the nucleophile? Electrophile? 2. Using your reaction mechanism from the above question, sketch the reaction coordinatediagram. What does the transition state most likely look like? What is the rate-determining step?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 CH₂OH