Reactions of alkyl halides with nucleophiles

36 questions on Reactions of alkyl halides with nucleophiles from the Haloalkanes and Haloarenes chapter: 8 NEET level, 15 JEE Main, 13 JEE Advanced. Each one opens with its answer and solution.

• Bromoethane on boiling with aqueous KOH gives mainly NEET level
• 2-Bromopropane on heating with alcoholic KOH gives mainly NEET level
• Bromoethane reacts with AgNO2 to give mainly NEET level
• Which of the following undergoes S_N2 reaction fastest with the same nucleophile under the same conditions? NEET level
• Hydrolysis of (CH3)3C-Br by dilute aqueous NaOH follows the rate law rate = k[(CH3)3CBr]. If [(CH3)3CBr] is doubled and [OH-] is tripled, the rate becomes JEE Main level
• Bromoethane is warmed with AgCN in ethanol. The main organic product is JEE Main level
• In the Williamson synthesis the best route to tert-butyl methyl ether, (CH3)3C-O-CH3, is JEE Main level
• Chlorobenzene does not give phenol with aqueous NaOH at room temperature. The best reason is that JEE Main level
• For the reaction CH3CH2Br + CN- -> CH3CH2CN + Br- at the same temperature and concentrations, the rate is highest in JEE Main level
• A mixture of bromobenzene and bromoethane is treated with sodium in dry ether. Counting only products formed by carbon-carbon coupling (and ignoring elimination... JEE Main level
• In which of the following reactions is an alkene the major organic product? JEE Main level
• A sample of 0.20 mol of 2-hydroxybut-3-ynoic acid, HC#C-CH(OH)-COOH, is treated with excess CH3MgBr in dry ether. Assume every acidic hydrogen (the O-H of the a... JEE Main level
• Bromoethane is warmed with AgCN to give a compound P. P is then boiled with dilute aqueous acid. The organic products are JEE Advanced level
• Which of the following statements are correct? JEE Advanced level
• Propyne is treated with NaNH2 in liquid NH3, and then 2-bromo-2-methylpropane is added. The main outcome is JEE Advanced level
• 2-Bromo-2-methylbutane is heated with alcoholic KOH and the major organic product is isolated. This product is then treated with HBr in the presence of a peroxi... JEE Advanced level
• Consider the following aryl halides toward hot aqueous NaOH (nucleophilic aromatic substitution): I, chlorobenzene; II, 1-chloro-4-nitrobenzene; III, 1-chloro-2... JEE Advanced level
• 2-Bromo-2-methylpropane is hydrolysed in 80% aqueous ethanol. Which statements are correct? JEE Advanced level
• Which alkyl bromide reacts fastest with NaI in dry acetone (SN2 conditions)? NEET level
• Ethyl bromide is heated with AgNO2 in ethanol. The major organic product is NEET level
• 2-Bromopropane is heated with alcoholic KOH. The major product is NEET level
• The hydrolysis of tert-butyl bromide in water follows the SN1 mechanism. Its rate law is NEET level
• Arrange the following in decreasing order of rate of SN1 solvolysis in aqueous ethanol. JEE Main level
• Methyl tert-butyl ether, CH3-O-C(CH3)3, is to be made in good yield by an SN2 Williamson synthesis. The correct pair of reactants is JEE Main level
• Which sequence correctly lists the methyl halides in increasing order of rate of SN2 reaction with a given nucleophile? JEE Main level
• The SN2 reaction of CH3CH2CH2Br with sodium azide, NaN3, is fastest in which solvent? JEE Main level
• Propyne is treated with NaNH2 in liquid NH3 and the resulting anion is then treated with bromoethane. The product is JEE Main level
• Which of the following halides do NOT undergo SN1 or SN2 substitution readily under ordinary conditions? JEE Main level
• A mixture of CH3Br and CH3CH2Br is treated with sodium metal in dry ether (Wurtz reaction). Assume only C-C coupling takes place (no elimination). How many diff... JEE Main level
• (R)-2-Bromobutane reacts with NaI in dry acetone to give X, and X reacts with sodium ethanoate to give Y. Assume each step is a single clean SN2 reaction with i... JEE Advanced level
• 1-Bromopropane is heated with AgCN to give A. On hydrolysis with dilute acid, A gives methanoic acid and an organic compound B. B is JEE Advanced level
• 2-Bromo-2-methylbutane is heated with alcoholic KOH and the major alkene is subjected to reductive ozonolysis. The carbonyl compounds obtained are JEE Advanced level
• Bromoethane is treated with KCN in ethanol to give P. P is reduced with LiAlH4 to give Q, and Q is treated with a large excess of CH3I in the presence of base. ... JEE Advanced level
• 4-Bromobutan-1-ol is treated with one equivalent of NaH in dry THF. The major product, formed by an intramolecular SN2 reaction, is JEE Advanced level
• Consider the following reactions of CH3Br and (CH3)3CBr with aqueous NaOH at fixed temperature. Assume CH3Br reacts only by the SN2 path and (CH3)3CBr only by t... JEE Advanced level
• In acetone with NaI (SN2 conditions), which of the following comparisons of reaction rates are correct? JEE Advanced level