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3. Predict the major product of the following reaction.

1. What is the electrophile in the electrophilic substitution reaction of benzene using HNO 3 and H 2 SO 4 ? A) SO 3 B) NO 3 C) NO 2 + D) NO +. 2. Which of the following represents the best reagent(s) for the electrophilic nitration of benzene?

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3. Predict the major product of the following reaction.

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  1. 1. What is the electrophile in the electrophilic substitution reaction of benzene using HNO3 and H2SO4? A) SO3 B) NO3 C) NO2+ D) NO+ 2. Which of the following represents the best reagent(s) for the electrophilic nitration of benzene? A) NO2 B) HNO2 C) HNO3 D) H2SO4, HNO3 3. Predict the major product of the following reaction. A) m-methylbenzenenitrile B) m-chlorobenzenenitrile C) o-cyanotoluene and p-cyanotoluene D) benzenenitrile

  2. 4. Predict the major product of the following reaction. A) 3-bromo-2-nitrophenol and 5-bromo-2-nitrophenol B) 1-bromo-2-nitrobenzene C) 2-bromo-6-nitrophenol and 4-bromo-2-nitrophenol D) 2-hydroxyaniline 5. Predict the major product of the following reaction. A) 2,4-dinitrophenol B) 3,4-dinitrophenol C) 2,4,5-trinitrophenol D) 3,4,5-trinitrophenol

  3. 6. The best sequence to use to form propylbenzene from benzene is • Friedel–Crafts alkylation using 1-chloropropane and aluminum trichloride. • Friedel–Crafts acylation followed by reduction. • electrophilic addition of 1-chloropropane. • D) nucleophilic aromatic substitution using propyl Grignard. 7. How would you synthesize the following compound? A) 1. MeCOCl, AlCl3 2. Zn (Hg) HCl B) 1. CH3COOH, AlCl3 2. H2, Pd 3. H2SO4, H2O, heat C) 1. CH3CH2Br, FeBr3 2. Br2, light 3. tBuONa, tBuOH, heat D) 1. CH3CHO, Mg in ether 2. NaBH4, MeOH 3. TsCl, pyridine 4. EtONa, EtOH

  4. 8. Which of the following aromatic compounds undergoes Friedel–Crafts alkylation with methyl chloride and aluminum chloride? • benzoic acid B) nitrobenzene • C) aniline D) toluene 9. Predict the major product of the following reaction. A) 1,2-dibromobenzene and 1,3-dibromobenzene B) 1,2-dibromobenzene and 1,4-dibromobenzene C) 1,3-dibromobenzene and 1,4-dibromobenzene D) 1,3-dibromobenzene

  5. 10. Predict the major product of the following reaction. A) 2-bromo-6-nitrobenzaldehyde and 2-bromo-4-nitrobenzaldehyde B) 2-bromo-3-nitrobenzaldehyde and 2-bromo-5-nitrobenzaldehyde C) 2-bromo-5-nitrobenzaldehyde D) 2-bromo-3-nitrobenzaldehyde

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