Reactions of aryl halides

38 questions on Reactions of aryl halides from the Haloalkanes and Haloarenes chapter: 6 NEET level, 16 JEE Main, 16 JEE Advanced. Each one opens with its answer and solution.

• Chlorobenzene is heated with aqueous NaOH at 623 K and 300 atm, and the product is then acidified. The final product is NEET level
• Aryl halides are much less reactive than alkyl halides toward nucleophilic substitution mainly because NEET level
• Nitration of chlorobenzene with a mixture of conc. HNO3 and conc. H2SO4 gives mainly NEET level
• Arrange the following in increasing order of reactivity toward aqueous NaOH (nucleophilic aromatic substitution). JEE Main level
• Bromobenzene and bromoethane are treated with sodium in dry ether. The main cross-coupled product is JEE Main level
• Iodobenzene is heated with copper powder. The main product is JEE Main level
• The experimental dipole moments are about 2.2 D for cyclohexyl chloride and 1.7 D for chlorobenzene. The best explanation of the lower value for chlorobenzene i... JEE Main level
• The melting points of the dichlorobenzenes are about 256 K for the ortho, 249 K for the meta and 326 K for the para isomer. The reason for the much higher value... JEE Main level
• For the SNAr reaction of 1-X-2,4-dinitrobenzene with sodium methoxide in methanol under identical conditions, the most reactive compound is the one with X = JEE Main level
• Chlorobenzene is treated with NaNH2 in liquid NH3. The product is JEE Main level
• Which of the following factors contribute to the low reactivity of chlorobenzene toward nucleophilic substitution (SN1 or SN2)? JEE Main level
• p-Chlorotoluene is treated with NaNH2 in liquid NH3. The amine products formed (in roughly equal amounts) are JEE Advanced level
• Chlorobenzene labelled with ^14C at the carbon bearing chlorine (C-1) is treated with NaNH2 in liquid NH3. Assume the labelled and unlabelled benzyne carbons ar... JEE Advanced level
• 3-Bromotoluene (m-bromotoluene) is treated with NaNH2 in liquid NH3, and the amines formed through all possible benzyne intermediates are isolated. Counting pos... JEE Advanced level
• Chlorobenzene is nitrated with conc. HNO3/conc. H2SO4, the para isomer is separated and heated with aqueous NaOH at 443 K, and the mixture is then acidified. Th... JEE Advanced level
• For the reaction with CH3O- in methanol (nucleophilic aromatic substitution by addition-elimination), select the correct statements. JEE Advanced level
• Which of the following statements about the electrophilic substitution of chlorobenzene are correct? JEE Advanced level
• Which of the following reactions of bromobenzene are correct? JEE Advanced level
• The dichlorobenzenes have these dipole moments: ortho about 2.5 D, meta about 1.7 D and para 0 D. Which statements are correct? JEE Advanced level
• Chlorobenzene is far less reactive than ethyl chloride towards nucleophilic substitution mainly because NEET level
• In the Dow process, chlorobenzene reacts with NaOH at 623 K and 300 atm. After acidification, the product is NEET level
• Halogen substituents on a benzene ring are NEET level
• Bromobenzene and bromoethane are treated with sodium metal in dry ether (Wurtz-Fittig reaction). The cross-coupled product is JEE Main level
• Chlorobenzene is mononitrated with conc. HNO3 and conc. H2SO4. Which statement is correct? JEE Main level
• The dipole moment of CH3Cl is about 1.9 D whereas that of C6H5Cl is about 1.7 D. The best explanation is that in chlorobenzene JEE Main level
• Arrange the following in decreasing order of reactivity towards aqueous NaOH (nucleophilic aromatic substitution): (I) chlorobenzene, (II) 1-chloro-4-nitrobenze... JEE Main level
• 1-Chloro-4-methylbenzene is treated with NaNH2 in liquid NH3. The number of different aromatic amine products (constitutional isomers) formed is JEE Main level
• Bromobenzene is converted to a Grignard reagent with Mg in dry ether, which is then poured over solid CO2 and acidified with dilute HCl. The final organic produ... JEE Main level
• In the reaction of 1-X-2,4-dinitrobenzene with sodium methoxide in methanol, the order of reactivity for X = F, Cl, Br, I (same conditions) is such that the mos... JEE Main level
• The melting points of dichlorobenzenes are: 1,2-isomer -17 degC, 1,3-isomer -25 degC, 1,4-isomer +53 degC. The high value for the 1,4-isomer is best explained b... JEE Main level
• 1-Chloro-2,4-dinitrobenzene reacts with sodium methoxide in methanol to give 2,4-dinitroanisole. Which statements are correct? JEE Advanced level
• Chlorobenzene labelled with ^14C at the carbon bearing Cl (C-1) is treated with KNH2 in liquid NH3. Which statements are correct? (Ignore isotope effects.) JEE Advanced level
• Under the conditions: aqueous NaOH at or below 368 K (and no catalyst), which of these aryl halides are converted into the corresponding phenol derivative? JEE Advanced level
• Chlorobenzene is nitrated with HNO3/H2SO4 and the major (para) product is separated, heated with aqueous NaOH at 433 K and finally acidified. The product is JEE Advanced level
• A mixture of bromobenzene and 1-bromo-4-methylbenzene (1 : 1) is treated with sodium in dry ether (Fittig reaction). Counting only the aromatic coupling product... JEE Advanced level
• 3-Chlorotoluene (1-chloro-3-methylbenzene) is treated with NaNH2 in liquid NH3. The number of different methylaniline (toluidine) isomers formed through benzyne... JEE Advanced level
• 2-Chlorotoluene is treated with NaNH2 in liquid NH3. Which statements are correct? JEE Advanced level
• Chlorobenzene (0.100 mol) is mononitrated with 80 percent total yield, and the nitro products are 70 mol percent para and 30 mol percent ortho (negligible meta)... JEE Advanced level