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Multiple Choice
Which set of reagents and conditions would most directly prepare ethyl acetate via an reaction?
A
Sodium acetate () plus bromoethane () in a polar aprotic solvent (e.g., acetone)
B
Acetic acid plus ethanol with catalytic under reflux (Fischer esterification)
C
Acetyl chloride () plus ethanol in the presence of pyridine
D
Ethyl bromide plus acetic acid () without base
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Verified step by step guidance
1
Identify the target molecule: ethyl acetate, which is an ester with the structure CH\_3COOCH\_2CH\_3.
Recall that an S\_N2 reaction involves a nucleophile attacking an electrophilic carbon, displacing a leaving group in a single step with inversion of configuration.
Determine the nucleophile and electrophile for the S\_N2 reaction to form ethyl acetate: the nucleophile should be the acetate ion (CH\_3COO\^-), and the electrophile should be an alkyl halide that can be attacked by the nucleophile, such as bromoethane (C\_2H\_5Br).
Choose a suitable solvent: polar aprotic solvents (e.g., acetone) favor S\_N2 reactions by stabilizing ions but not the nucleophile, increasing its reactivity.
Combine sodium acetate (source of acetate ion) with bromoethane in a polar aprotic solvent to allow the acetate ion to perform an S\_N2 attack on the ethyl bromide, forming ethyl acetate.