Nucleophilic acyl substitution of carboxylic acid derivatives

55 questions on Nucleophilic acyl substitution of carboxylic acid derivatives from the Organic Reaction Mechanisms I: Nucleophiles and Carbonyl Addition chapter: 11 NEET level, 22 JEE Main, 22 JEE Advanced. Each one opens with its answer and solution.

• Which of the following carboxylic acid derivatives is the most reactive towards nucleophilic acyl substitution? NEET level
• Acetyl chloride is treated with excess ammonia. The organic product is NEET level
• Acetic anhydride reacts with ethanol. The products are NEET level
• Ethyl acetate is heated with aqueous NaOH. The products are NEET level
• In the collapse of the tetrahedral intermediate formed from CH3-CO-X and a nucleophile, which group X is lost most easily? NEET level
• Benzoyl chloride reacts with aniline in the presence of a base. The main product is NEET level
• The esterification CH3COOH + C2H5OH <=> CH3COOC2H5 + H2O is reversible. Which condition drives it towards the ester? NEET level
• Acetamide is boiled with aqueous NaOH. The gas evolved and the salt formed are NEET level
• Which reagent converts benzoic acid into benzoyl chloride so that all by-products are gases? NEET level
• During hydrolysis of an ester by hydroxide, the hybridisation of the carbonyl carbon changes as NEET level
• Sodium acetate is treated with acetyl chloride. The products are NEET level
• Which of the following esters is hydrolysed fastest by aqueous NaOH at the same temperature? JEE Main level
• Acetyl chloride hydrolyses much faster than benzoyl chloride under the same conditions mainly because JEE Main level
• Amides are the least reactive carboxylic acid derivatives towards nucleophilic acyl substitution because JEE Main level
• Ethyl acetate is treated with excess CH3MgBr in dry ether followed by H3O+. The final organic product is JEE Main level
• Benzoyl chloride is treated with excess C2H5MgBr and then H3O+. The final product is JEE Main level
• Ethyl acetate in which the alkoxy oxygen is labelled with ^18O is hydrolysed with aqueous NaOH. The ^18O label is found in JEE Main level
• Exactly 2 mol of ammonia react with 1 mol of acetic anhydride. The products are JEE Main level
• Arrange in decreasing rate of reaction with methylamine: (I) benzoyl chloride, (II) benzoic anhydride, (III) methyl benzoate, (IV) N-methylbenzamide. JEE Main level
• Which alcohol undergoes Fischer esterification with acetic acid (acid catalyst, same conditions) at the highest rate? JEE Main level
• Which acid is esterified most slowly by methanol with a catalytic strong acid under identical conditions? JEE Main level
• Acetyl chloride reacts with 2 equiv of diethylamine. The organic product is JEE Main level
• Which ethyl benzoate is hydrolysed fastest by aqueous NaOH? JEE Main level
• In the reaction of ethanol with acetyl chloride, pyridine is added. Its role is to JEE Main level
• Acid hydrolysis of acetamide with aqueous HCl goes essentially to completion because JEE Main level
• Methyl benzoate is heated with a large excess of ethanol containing a little concentrated H2SO4. The main products are JEE Main level
• Match Column I with Column II. Column I: (P) CH3COCl + ethanol, pyridine; (Q) CH3COOC2H5 + aq. NaOH, heat; (R) CH3CONH2 + aq. NaOH, heat; (S) CH3COOH + ethanol,... JEE Main level
• Which of the following reagents convert CH3COOH into CH3COCl? JEE Main level
• Which of the following are hydrolysed faster than ethyl acetate by aqueous NaOH at the same temperature and concentration? JEE Main level
• Ethyl benzoate is treated with excess CH3MgBr in dry ether, then H3O+. Which statements are correct? JEE Main level
• For the tetrahedral intermediate of nucleophilic acyl substitution, which statements are correct? JEE Main level
• Which statements about N-methylacetamide are correct? JEE Main level
• One mole of ethyl benzoate and one mole of benzoyl chloride are mixed and treated with a large excess of CH3MgBr in dry ether, then H3O+. Assume each acyl compo... JEE Main level
• Ethyl 4-hydroxybenzoate is treated with a large excess of CH3MgBr in dry ether: (i) CH3MgBr (excess), dry ether; (ii) H3O+. The final product is JEE Advanced level
• Ethyl 3-oxobutanoate is treated with 1 equiv of CH3MgBr in dry ether at 0 degC, followed by a quick H3O+ work-up. The result is JEE Advanced level
• Diethyl carbonate, (C2H5O)2C=O, is treated with excess C2H5MgBr, then H3O+. The final product is JEE Advanced level
• Oxolan-2-one (gamma-butyrolactone) is treated with excess CH3MgBr in dry ether, then mild aqueous NH4Cl work-up. The product is JEE Advanced level
• Methyl 4-(chlorocarbonyl)benzoate is treated with 1 equiv of aniline and pyridine at 0 degC in dry CH2Cl2. The product is JEE Advanced level
• Butanoic acid is converted as follows: (i) SOCl2; (ii) excess NH3; (iii) P2O5, heat; (iv) CH3MgBr (1 equiv), dry ether; (v) H3O+. The final product is JEE Advanced level
• Methyl 4-aminobutanoate is heated (neat, with removal of methanol). The organic product is JEE Advanced level
• 5-Hydroxypentanoic acid is warmed with a trace of H2SO4 under high dilution. The main product is JEE Advanced level
• Acetic formic anhydride, HCO-O-CO-CH3, reacts with 1 equiv of methylamine at low temperature. The main product is JEE Advanced level
• Succinic anhydride is treated with 1 equiv of aniline, then the product is heated strongly (dehydration). The final organic product is JEE Advanced level
• Phthalic anhydride is treated with: (i) CH3OH (1 equiv), room temperature; (ii) SOCl2; (iii) CH3NH2 (2 equiv), 0 degC. The final product is JEE Advanced level
• Which reagent converts benzoyl chloride to acetophenone, stopping at the ketone stage in high yield? JEE Advanced level
• Assertion (A): Alkaline hydrolysis of ethyl acetate with excess NaOH is essentially irreversible. Reason (R): Hydroxide is a stronger nucleophile than water. JEE Advanced level
• Assertion (A): Acetyl chloride is more reactive towards nucleophiles than ethyl acetate. Reason (R): The chlorine atom donates its lone pair into the carbonyl g... JEE Advanced level
• Assertion (A): When methyl benzoate is treated with only 1 equiv of CH3MgBr, acetophenone cannot be obtained as the main product. Reason (R): Acetophenone is mo... JEE Advanced level
• Which of the following give a tertiary alcohol when treated with excess CH3MgBr (dry ether) followed by H3O+? JEE Advanced level
• Each compound (1 mol) reacts with a large excess of CH3MgBr to form the final tertiary alkoxide. Counting the acidic O-H hydrogen as consuming 1 mol of Grignard... JEE Advanced level
• Which acids are esterified more slowly than acetic acid by methanol with a catalytic strong acid under identical conditions? JEE Advanced level
• Which statements are correct? JEE Advanced level
• In the acid-catalysed Fischer esterification of acetic acid with ethanol, which statements are correct? JEE Advanced level
• Which compounds evolve NH3 gas on heating with concentrated aqueous NaOH? JEE Advanced level
• Benzoic acid (C6H5COOH, 12.2 g) is converted to benzoyl chloride with excess SOCl2 (isolated yield 90%). The acid chloride is then treated with excess aniline a... JEE Advanced level