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Correct Answer: C
Correct Answer: C
Method / Topic: Organic Chemistry
The correct option matches the required rule and the given information.
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Correct Answer: C
Method / Topic: Organic Chemistry
Ionization produces an approximately trigonal-planar, sp2-hybridized carbocation at carbon 2. Water can approach either face of this intermediate, generating both configurations after deprotonation. The product may not be perfectly racemic because ion-pair and solvent-cage effects can partially shield one face. This conclusion follows from electron flow, functional-group behavior, and the stated experimental conditions. For MCAT organic chemistry, first mark the nucleophile, electrophile, leaving group, and any resonance-stabilized intermediate; then track bonds rather than memorizing a product name. Check stereochemistry, charge, and carbon count before choosing an
, and interpret evidence without overclaiming. Always reconcile the proposed structure with every observation in the
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PASSAGE 2 — SUBSTITUTION AT A CHIRAL CENTER A researcher studies the reaction of optically pure (R)-2-bromobutane with sodium ethoxide in ethanol. At low temperature, substitution competes with elimination. In a separate trial, the same alkyl halide is treated with water in a polar protic solvent and allowed to react through a carbocation intermediate. Products are analyzed by polarimetry and gas chromatography. QUESTION 6: Why can an SN1 reaction of optically pure (R)-2-bromobutane produce both enantiomers of 2-butanol?
Explanation
Correct Answer: C
Method / Topic: Organic Chemistry
The correct option matches the required rule and the given information.
Short Explanation
Detailed Explanation
Correct Answer: C
Method / Topic: Organic Chemistry
Ionization produces an approximately trigonal-planar, sp2-hybridized carbocation at carbon 2. Water can approach either face of this intermediate, generating both configurations after deprotonation. The product may not be perfectly racemic because ion-pair and solvent-cage effects can partially shield one face. This conclusion follows from electron flow, functional-group behavior, and the stated experimental conditions. For MCAT organic chemistry, first mark the nucleophile, electrophile, leaving group, and any resonance-stabilized intermediate; then track bonds rather than memorizing a product name. Check stereochemistry, charge, and carbon count before choosing an
, and interpret evidence without overclaiming. Always reconcile the proposed structure with every observation in the
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