1. Answer the questions about the following reaction: (a) Draw in the arrows that can be used make this reaction occur and draw in all products of this reaction. Be sure to include any relevant stereochemistry. F ☑Na +5 S Na + CI (b) In which solvent would this reaction proceed the fastest (Circle one) Methanol Acetone (c) Imagine that you are working for a chemical company and it was your job to perform a similar reaction to the one above, with the exception of the S atom in this reaction being replaced by an O atom. During the reaction, you observe the formation of three separate molecules instead of the two molecules seen here. What is the likeliest other product that is formed? Draw it in the box provided.

If Zaitsev's rule does not apply and the base is bulky then how will the product look?

iii) 2-Bromo-2-cyclopropylpropane will undergo an SN1 reaction called solvolysis in methanol to give several products, two of which are shown below. Use curly arrows to show how the formation of these two products occurs mechanistically.

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QUESTION 2a between one equivalent of HBr with the compound shown below? What would be the major 1,2 and 1,4 products formed by the reaction Indicate which is the kinetic and which is the thermodynamic product and the reasoning for your choice (1-2 sentences maximum). Draw an energy diagram to help explain your choice. intermediates. Also, how would it is possible to favor formation of the 1,4 over 1,2 product and the Show the complete arrow pushing mechanism for the formation of each product and all 1,2 over 1,4 product. HBr (1 eq)

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43C\ ......cion 2 (a) What reaction will occur if a catalytic amount of the base sodium ethoxide is added to acetone? Propose a structure of the product from this reaction. HK CH₂ NaOEt (0.05 eq) (b) What product would be expected if acetone were added to an excess of a stronger base (e.g. LDA)?

Draw the major organic product(s) for the following. - You may assume each reaction occurs just one time. - Show or depict any relevant stereochemistry in the products [R/S or E/Z labels are not needed].