4. For each of the following reactions, draw the arrow-pushing mechanism that leads to the product shown. Use your knowledge of pKa's, nucleophiles, and electrophiles to determine if the reaction shown is likely to happen, and briefly explain your rationale. In the cases where the reaction drawn is not likely, draw the mechanism of the correct reaction. (30 pts) a) + Na + Br NH2 + CH3-1 + |¯ H H Na + Br OH + Br + NH₂ + OH CI + NaBr + + NaBr OH Br + HF + HCI NH

Yead. III. Show a complete synthesis of the following molecule starting with cyclohexane (as many times as you wish), any molecules of three (3) carbons or fewer, and any other reagents. (16 pts) Zoxo 5 Br BV-Br +Br HBV Br-Br Br Br Br Br Br HBV Br Br Brz ← ·Br Br BL Δ H G HO) TH F -OH он して

q, a Proton transfer d = Electrophilic addition g = S 1 Nucleophilic substitution b = N 'N' Lewis acid/base e = E1 Elimination h = S_2 Nucleophilic substitution c = Radical chain substitution f = E2 Elimination Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - i for your answers. 12

Please give a reasonable mechanism for the following reaction using a multiple component reactions. Please draw it out and write out the steps. PLEASE SHOW WITH ARROWS. 5 PhNH + n-Bu 10 mol% TI (NM)2(doma) + ABU-NC tol 100 °C, 48 h, 77% Bu n-Bu

h- Syl Nucleophilic substitution i- Sy2 Nucleophilic substitution j- Electrophilic aromatic substitution a - Proton transfer e - Electrophilic addition b- Lewis acid/base f-E1 Elimination c- Radical chain substitution d = Radical chain addition. g- E2 Elimination Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - j for your answers. HI AICI3 Cl- AICI, OEt Na OEt OEt HOET Na AIBN CN 70° poly(acrylonitrile) (Orlon, Acrilan)

Use the information below to identify and explain the relationship between the basicity of the two nucleophiles and their nucleophilicities

Which of the following statements is TRUE regarding the reaction below? Options:   The IR spectrum of the major organic product will show a broad absorption between 3000-3500 cm-1.   The mass spectrum of the major organic product will show an M+2 peak in the molecular ion region.   The reaction should proceed without carbocation rearrangement.   The alkene is the electrophile and water is the nucleophile in the first step.   HSO4- is the dominant nucleophile in the second step.

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Use the reaction given below to answer the following questions. A + р CH3OH 12pt Paragraph B H₂O+ C a) What are the approximate pKas of compounds A and B? b) The reaction given above is irreversible. Give a detailed explanation of the reaction and reaction mechanism. Your explanation should indicate your knowledge of the reactivity of carboxylic acid derivatives. BIU + CH3NH3+ D V 0 words

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