From the lists of available reagents select the one(s) you would use to in a preparation of acetophenone (phenyl methyl ketone) from methyl benzoate. (In no case are more than three steps necessary.) Reagents Available a. CH3COCI, AICI3 d. CH3CHO b. (CH3)2CuLi e. Hg(OAc)2, H2O; then NaBH4 g. Mg h. NaOH, H₂O j. SOCI₂ c. CH3MgBr, then H3O+ H30* f. KMnO4, H₂O i. Dess-Martin periodinane List reagents by letter in the order that they are used; example: fa. Reagents used:

This is a multistep syntheses. More than one reagent/reaction will be necessary to produce the product. Provide all necessary reaction conditions (HBr, HgSO4, etc.) and the products produced after each step of the synthesis.

1a). Plan a synthesis of 3,4-dibromoaniline, starting from benzene. 4steps are required, lists reagents needed and draw in the intermediates.

Br Brz CH3 CH3 H3C CH2CI2 H3C Br Electrophilic addition of bromine, Br2; to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl). In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br: :Br: .CH3 H3C H3C CH3 Br: