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(3 write the structure of a major product when benzene reacts with neopentyl bromide (1-bromo-2,2-dimethylpropane) in the presence of AICIslheat. Show the reaction mechanism of this reaction and name the product. (4) Using retrosynthetic analysis, devise a synthesis of terephthalic acid from benzene by using any necessary organic and inorganic reagent. (Assume that ortho. and para-somers are easily separable in the laboratory.) ooH Coon (5) identify compounds A-C in the retrosynthesis shown below and suggest reagents for each synthetic step. benzene
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Answer (3)

Answer: (3) H2C CH H3C, ,CH3 CH3 Br neoPentyl bromide Friedel Craft Alkylation 1-tert-pentylbenzene 2-Methylbutyl)Benzene Benzene Mechanism 1) Generation of an Electrophile H3C CH3 H3C CH3 Methyl (CH3)Shift CH H2 Carbocation rearrangent AlCI 3 AlChBr 3 AICI3Br73 neoPentyl bromide 10 Carbocation Least stable 3° Carbocation Most stable 2) Elec trophilic Aromatic Substitution reaction H3C H3C CH H2C CH2 CH3 CH3 CH3 H3C H 12 Rearomatization se Sigma complex Resonance staabilization

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