Reactions of ethers and epoxides

28 questions on Reactions of ethers and epoxides from the Organic Reaction Mechanisms III: Nucleophilic Substitution chapter: 6 NEET level, 11 JEE Main, 11 JEE Advanced. Each one opens with its answer and solution.

• Anisole (C6H5-O-CH3) is heated with one equivalent of concentrated HI. The products are NEET level
• Ethyl methyl ether (CH3-O-CH2CH3) reacts with one equivalent of cold concentrated HI. The major products arise by SN2 attack of iodide on the less hindered carb... NEET level
• Cyclohexene is treated with meta-chloroperoxybenzoic acid (m-CPBA) in dichloromethane. The main product is NEET level
• Ethylene oxide is treated with CH3MgBr in dry ether and the mixture is then worked up with dilute acid. The product is NEET level
• tert-Butyl methyl ether, (CH3)3C-O-CH3, is treated with one equivalent of HI at room temperature. Because the tertiary carbocation is easily formed (SN1), the p... NEET level
• The best Williamson synthesis of tert-butyl methyl ether, (CH3)3C-O-CH3, uses NEET level
• Ethyl phenyl ether is heated with excess HBr. The products are JEE Main level
• tert-Butyl ethyl ether is treated with one equivalent of anhydrous HI at 0 degC. Taking the conventional SN1 outcome with substitution by iodide, the products a... JEE Main level
• 1,4-Dimethoxybenzene is heated with excess concentrated HI. The products are JEE Main level
• 2,2-Dimethyloxirane (isobutylene oxide) is warmed with methanol containing a few drops of H2SO4. The major product is JEE Main level
• 2-Methyloxirane (propylene oxide) is treated with CH3MgBr in dry ether, followed by aqueous NH4Cl. The product is JEE Main level
• Cyclohexene oxide is treated with dilute aqueous H2SO4. The product is JEE Main level
• Which of the following halohydrins gives cyclohexene oxide readily when treated with aqueous NaOH? JEE Main level
• Cyclohexyl methyl ether is best prepared by the Williamson method from JEE Main level
• (Z)-But-2-ene is treated with m-CPBA in dichloromethane. The product is JEE Main level
• Which of the following ethers give (CH3)3C-I as one product when treated with one equivalent of HI at room temperature (SN1 cleavage at the tertiary carbon)? JEE Main level
• 2-Methyloxirane is opened by each of the following under basic or neutral nucleophilic conditions. In which cases does the nucleophile bond to the CH2 carbon of... JEE Main level
• (R)-2-Methoxybutane is treated with one equivalent of HI at low temperature. Iodide attacks the carbon that is least hindered. What is the chiral organic produc... JEE Advanced level
• (R)-2-Methyloxirane is treated with aqueous NaCN (basic nucleophilic conditions). What is the product? JEE Advanced level
• (2R,3R)-2,3-Dimethyloxirane reacts with NaN3 in aqueous solution (followed by protonation). Azide attacks one ring carbon by SN2. The product is JEE Advanced level
• (2S,3S)-3-Bromobutan-2-ol is treated with aqueous NaOH. An intramolecular SN2 reaction occurs in which the alkoxide displaces bromide. The product is JEE Advanced level
• Match each ether in Column I with the products obtained when one mole is cleaved with excess HI in the cold or on gentle warming, taking the usual SN1 or SN2 ru... JEE Advanced level
• 1-Methylcyclohexene oxide (the epoxide of 1-methylcyclohexene) is treated with methanol containing a catalytic amount of H2SO4. Which product is formed mainly? JEE Advanced level
• Which statements about epoxidation of alkenes with a peroxy acid are correct? JEE Advanced level
• Cyclohexene oxide is treated with different reagents. Which products are correctly stated? JEE Advanced level
• Which ethers give a phenol as one of the products when heated with one equivalent of concentrated HI? JEE Advanced level
• 2,2-Dimethyloxirane is opened under different conditions. Which statements are correct? JEE Advanced level
• One mole of 1-methoxy-4-(2-methoxyethoxy)benzene, CH3O-C6H4-O-CH2CH2-O-CH3 (para-disubstituted ring), is heated with a large excess of concentrated HI until eve... JEE Advanced level