Predict the product(s) of each of the following multistep reactions.
(a)

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Step 1: Analyze the first reaction step. The reagents CH3Cl and AlCl3 indicate a Friedel-Crafts alkylation. The benzene ring will undergo electrophilic aromatic substitution, where the CH3 group (methyl) will be added to the ring. Since the benzene ring already has a chlorine substituent, the methyl group will likely add to the ortho or para position due to the electron-withdrawing nature of chlorine.

Step 2: Examine the second reaction step. NBS (N-bromosuccinimide) in the presence of heat is used for allylic or benzylic bromination. The methyl group added in the first step is at the benzylic position, so this step will replace one of the hydrogens on the benzylic carbon with a bromine atom, forming a benzyl bromide.

Step 3: Consider the third reaction step. NaCN in DMSO is a nucleophilic substitution reaction. The bromine atom on the benzyl bromide will be replaced by a cyanide group (-CN) through an SN2 mechanism, resulting in a benzyl cyanide product.

Step 4: Combine the transformations. The final product will have the original benzene ring with a chlorine substituent, a methyl group at the para or ortho position relative to chlorine, and a cyanide group attached to the benzylic carbon.

Step 5: Verify the regioselectivity and stereochemistry. Ensure that the positions of the substituents (chlorine, methyl, and cyanide) are consistent with the directing effects and steric considerations of the reactions.

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