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

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

Draw the structure(s) of the major organic product(s) obtained after workup of the following reaction. о + сн CH₂-C-Cl CH3 1. in benzene 2. aqueous HCI You do not have to consider stereochemistry. • . If no reaction occurs, draw the organic starting material. • • • Include the amine from which the enamine was derived. Include counter-ions, e.g., Na+, I, in your submission, but draw them in their own separate sketcher. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Θ CH3 CH3 CH3 ? ChemDoodle" remove

How to attempt this problem?

Treatment of acetylene with a suitable base affords lithium acetylide, which was used as a reagent in a partial synthesis of the antitumor natural product (+)-acutiphycin. (Org. Lett. 2014, 16, 1168-1171) Possible bases to consider H-C=C-H Acetylene Step 1 Li :Base T H-O: Li Lithium hydroxide (LiOH) three steps Lithium acetylide Draw the structure of lithium acetylide. Draw Your Solution di. Η Η Η Η | | | | H-C-C-C-C: II HH HH Butyllithium (BuLi) OR CEC- Li OH CH3 -H CH3 Lithium diisopropyl amide (LDA) OMe H3C H H₂C many steps Li HO OH I (+)-Acutiphycin CH3 CH₂ "OH

For the following reaction, draw the likely mechanism and try to write out that mechanism in words OH I equivalent OH 1 eq.

In this acid-base reaction, why does the nucleophile attack the CH3 and not a hydrogen from the methyl group instead?