The chlorination reaction of the following molecule yields one major mono-chloro product. Cl2 AICI3 a. Draw the structure of this product b. The reaction involves formation of reactive intermediate cations. Draw all the important resonance contributors involved in the reaction mechanism, show your work! ZI

4. Consider the reactants below. Answer the following questions about the reaction mechanism and products. Br x a. What is the degree of substitution of the alkyl halide? b. What type of base and nucleophile is the water molecule? A H₂O c. What type of mechanism is favored in the reaction of tertiary halides and weak bases/nucleophiles with heat applied? d. Draw the structure of the product for the reaction e. Provide an arrow-pushing mechanism for the formation of the product.

Using the electron-pushing diagram shown, draw the product of the reaction, including nonbonding electrons and charges where appropriate. a H B H H Draw the product. Add charges and electrons where needed. Select Draw Rings More 3 с H B O Erase Q2 Q

4. Use the reactant below to perform two separate reactions. Give the mechanism(s) and product(s) for each reaction. Show stereochemistry and be clear your work. H₂SO4, EtOH D !!!H Me NaOEt, EtOH