Ethers: Williamson synthesis and cleavage

36 questions on Ethers: Williamson synthesis and cleavage from the Alcohols, Phenols and Ethers chapter: 8 NEET level, 14 JEE Main, 14 JEE Advanced. Each one opens with its answer and solution.

• The Williamson synthesis of ethers proceeds by which mechanism? NEET level
• Anisole, C6H5-O-CH3, is heated with one equivalent of HI. The products are NEET level
• Ethanol is heated with conc. H2SO4 at 413 K with the alcohol in excess. The main product is NEET level
• The best way to prepare tert-butyl methyl ether by Williamson synthesis is NEET level
• Which combination gives ethyl isopropyl ether (2-ethoxypropane) in the best yield? JEE Main level
• Isopropyl methyl ether (2-methoxypropane) is heated with one equivalent of HI. The products are JEE Main level
• Anisole is treated with ethanoyl chloride and anhydrous AlCl3. The major product is JEE Main level
• 2-Methyloxirane is treated with CH3ONa in methanol and then neutralised. The major product is JEE Main level
• Select the correct statements about ethers. JEE Main level
• 3,3-Dimethylbut-1-ene is treated with Hg(OAc)2 in methanol, followed by NaBH4. The major product is JEE Main level
• Cyclohexene oxide is treated with methanol containing a catalytic amount of H2SO4. The major product is JEE Main level
• One mole of CH3-O-CH2CH2-O-C6H5 (1-methoxy-2-phenoxyethane) is heated with a large excess of hot, concentrated HI. Assume that every aliphatic ether C-O bond is... JEE Advanced level
• 5-Bromopentan-1-ol is treated with NaH in an inert solvent to give a cyclic ether Z, which is then heated with excess conc. HI. The final organic product is JEE Advanced level
• A compound C_5H_12O does not evolve hydrogen with sodium. When treated with one equivalent of HI at room temperature it gives methanol and a tertiary alkyl iodi... JEE Advanced level
• Select the Williamson syntheses that give the stated ether as the major product. JEE Advanced level
• Assertion (A): tert-Butyl phenyl ether reacts with one equivalent of HI to give phenol and 2-iodo-2-methylpropane. Reason (R): Cleavage of aryl alkyl ethers by ... JEE Advanced level
• 2,2-Dimethyloxirane is subjected to the following conditions. Select all correct product assignments. JEE Advanced level
• (R)-2-Methoxybutane is heated with one equivalent of HI under mild conditions, so that the reaction takes place by SN2 at the less hindered carbon. The products... JEE Advanced level
• Williamson synthesis of ethoxyethane (diethyl ether) uses NEET level
• Anisole (C6H5-O-CH3) is heated with excess hydroiodic acid. The products are NEET level
• An excess of ethanol is heated with conc. H2SO4 at 413 K. The main organic product is NEET level
• On standing in air and light, diethyl ether slowly forms NEET level
• The best Williamson route to tert-butyl methyl ether, (CH3)3C-O-CH3, is JEE Main level
• Methyl isopropyl ether, CH3-O-CH(CH3)2, is treated with one equivalent of HI and warmed. The products are JEE Main level
• tert-Butyl ethyl ether is treated with one equivalent of HI at low temperature. The products are JEE Main level
• Anisole is nitrated with HNO3/H2SO4. The main products are JEE Main level
• Which pairs of reactants give an alkene as the major product, instead of an ether, under Williamson conditions? JEE Main level
• Ethylene oxide is heated with ethanol in the presence of a trace of acid. The main product is JEE Main level
• 2-Methyloxirane (propylene oxide) is treated with CH3ONa in methanol (basic conditions), then work-up. The major product is JEE Main level
• 1-Methoxy-4-(2-methoxyethoxy)benzene, CH3O-C6H4-O-CH2CH2-O-CH3 (the two oxygens on the ring are para), is heated with a large excess of concentrated HI. Count t... JEE Advanced level
• An ether X, C5H12O, does not react with sodium metal. With one equivalent of HI it gives a tertiary alkyl iodide and methanol. X is JEE Advanced level
• Phenol is treated with NaOH and then CH3I to give X. X is treated with Br2 in ethanoic acid to give Y (major product). Y is then heated with excess hot HI. The ... JEE Advanced level
• 4-Bromobutan-1-ol is treated with NaH in THF to give X. X is then heated with excess concentrated HI. The final organic product is JEE Advanced level
• Which of the following ethers give an alkyl iodide and an alcohol (or phenol) on cleavage with one equivalent of HI as stated? JEE Advanced level
• Ethyl phenyl ether can be obtained in good yield by which of the following? JEE Advanced level
• Which statements about anisole, C6H5-O-CH3, are correct? JEE Advanced level