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Method / Topic: Organic Chemistry
During nucleophilic acyl substitution, the original carbonyl oxygen remains attached to the acyl carbon through formation and collapse of the tetrahedral intermediate. It therefore becomes one of the oxygens of the carboxylate product rather than moving to the alcohol or catalytic residues. To solve this MCAT organic chemistry item, identify the reacting functional group, nucleophile, electrophile, and leaving group. Follow bonds: state which bond forms, which bond breaks, and how charge changes. For carbonyl chemistry, distinguish addition from acyl substitution and track the original carbonyl oxygen. For oxidation or reduction, compare carbon bonds to oxygen and hydrogen. For stereochemistry, decide whether the center is planar, chiral, or attacked from one face. In separation and spectroscopy
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Correct Answer:
Method / Topic: Organic Chemistry
During nucleophilic acyl substitution, the original carbonyl oxygen remains attached to the acyl carbon through formation and collapse of the tetrahedral intermediate. It therefore becomes one of the oxygens of the carboxylate product rather than moving to the alcohol or catalytic residues. To solve this MCAT organic chemistry item, identify the reacting functional group, nucleophile, electrophile, and leaving group. Follow bonds: state which bond forms, which bond breaks, and how charge changes. For carbonyl chemistry, distinguish addition from acyl substitution and track the original carbonyl oxygen. For oxidation or reduction, compare carbon bonds to oxygen and hydrogen. For stereochemistry, decide whether the center is planar, chiral, or attacked from one face. In separation and spectroscopy
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