Dissolving metal reductions (Birch, Na/NH3)

37 questions on Dissolving metal reductions (Birch, Na/NH3) from the Reduction, Oxidation and Hydrolysis in Organic Chemistry chapter: 8 NEET level, 15 JEE Main, 14 JEE Advanced. Each one opens with its answer and solution.

• Reduction of but-2-yne with sodium in liquid ammonia gives NEET level
• Birch reduction of benzene (Na, liquid NH3, ethanol) gives NEET level
• Ethyl butanoate is reduced to butan-1-ol (plus ethanol) by NEET level
• The deep blue colour of a dilute solution of sodium in liquid ammonia is due to NEET level
• Anisole (methoxybenzene) is reduced with Na in liquid NH3 containing ethanol. The major product is JEE Main level
• Benzoic acid is subjected to Birch reduction (Na, liquid NH3, ethanol), then acidified. The product is JEE Main level
• On Birch reduction (Na, liquid NH3, ethanol), the substituent of which compound ends up on an sp3 carbon of the product ring? JEE Main level
• In a Birch reduction the alcohol (for example ethanol) added to the Na/NH3 mixture serves as JEE Main level
• The sequence benzene xrightarrowNa, liq. NH3, EtOH xrightarrowH2 (excess), Pd-C finally gives JEE Main level
• Which statements about the Birch reduction (Na, liquid NH3, ethanol) are correct? JEE Main level
• 1,4-Dimethoxybenzene undergoes Birch reduction with Na, liquid NH3 and ethanol. The major product is JEE Main level
• Anisole is reduced by Na/liquid NH3/ethanol and the product is warmed with aqueous HCl, which hydrolyses the enol ether and also conjugates the double bond. The... JEE Advanced level
• Hex-3-yne is treated with (i) Na in liquid NH3; (ii) mCPBA; (iii) aqueous H3O+ (anti opening of the epoxide). The product is JEE Advanced level
• Which statements about but-2-yne are correct? JEE Advanced level
• In which of the following does the Birch reduction (Na, liquid NH3, ethanol) give a product in which every substituent sits on an sp2 carbon of the 1,4-diene? JEE Advanced level
• Theoretically, how many moles of sodium are consumed in the Bouveault-Blanc reduction of one mole of diethyl butanedioate, C2H5OOC-CH2CH2-COOC2H5, in ethanol to... JEE Advanced level
• Hex-3-yne is reduced with Na in liquid NH3 and the product is treated with Br2 in CCl4 (anti addition). The final product is JEE Advanced level
• Assertion (A): Birch reduction of anisole gives 1-methoxycyclohexa-1,4-diene and not 3-methoxycyclohexa-1,4-diene. Reason (R): The electron-donating methoxy gro... JEE Advanced level
• Benzene is treated with Na in liquid NH3 containing ethanol. The major organic product is NEET level
• Na in liquid NH3 reduces but-2-yne mainly to NEET level
• The deep blue colour of a solution of sodium in liquid ammonia is due to NEET level
• Ethyl butanoate is heated with sodium metal in absolute ethanol (Bouveault-Blanc reduction). The main organic product is NEET level
• Anisole (methoxybenzene) is reduced with Na in liquid NH3 and ethanol. The major product is JEE Main level
• Benzoic acid is reduced with Na in liquid NH3 and ethanol, and the mixture is acidified. The major product is JEE Main level
• Toluene is reduced by Na in liquid NH3 with ethanol to the major Birch product. How many sp^3 hybridised carbon atoms (ring plus substituent) does this product ... JEE Main level
• 1-Hexyne is added to Na in liquid NH3 and no alcohol or other proton source is added. The principal outcome is JEE Main level
• Pent-2-yne is reduced with Na in liquid NH3 to trans-pent-2-ene. The stereochemistry arises mainly because JEE Main level
• Ethyl butanoate is treated with finely dispersed sodium in refluxing dry xylene, and the product is then worked up with water and acid (acyloin condensation). T... JEE Main level
• Benzoic acid (molar mass 122 g mol^-1) is converted by Birch reduction into cyclohexa-2,5-diene-1-carboxylic acid (molar mass 124 g mol^-1). Starting from 12.2 ... JEE Main level
• Acetone is treated with magnesium amalgam in dry benzene, followed by water. The product is JEE Main level
• 1-Methoxy-4-methylbenzene is subjected to Birch reduction (Na, liquid NH3, ethanol). The major product is JEE Advanced level
• Anisole is reduced with Na in liquid NH3 and ethanol, and the crude product is then stirred briefly with cold, dilute aqueous oxalic acid so that no double-bond... JEE Advanced level
• Naphthalene is reduced with Na in liquid NH3 containing ethanol to give a dihydro compound C10H10. This is ozonised (O3, then Zn/H2O). The major organic product... JEE Advanced level
• Which of the following statements about the Birch reduction (Na, liquid NH3, ethanol) are correct? JEE Advanced level
• Which of the following reductions with Na in liquid NH3 give the trans alkene as the major organic product? JEE Advanced level
• Which of the following transformations are correctly matched with the product after aqueous work-up? JEE Advanced level
• Which of the following statements about the mechanism of the Birch reduction of benzene (Na, liquid NH3, ethanol) are correct? JEE Advanced level