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Correct Answer: D
Correct Answer: D
Method / Topic: Organic Chemistry
The correct option matches the required rule and the given information.
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Correct Answer: D
Method / Topic: Organic Chemistry
A small nucleophile can approach the electrophilic carbon for backside attack, and lower temperature reduces the entropic advantage of elimination. Bulky strong bases have difficulty attacking carbon and instead remove a beta hydrogen, especially when heated, thereby favoring E2. 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 5: Which change would most strongly favor SN2 substitution over E2 elimination for a secondary alkyl halide?
Explanation
Correct Answer: D
Method / Topic: Organic Chemistry
The correct option matches the required rule and the given information.
Short Explanation
Detailed Explanation
Correct Answer: D
Method / Topic: Organic Chemistry
A small nucleophile can approach the electrophilic carbon for backside attack, and lower temperature reduces the entropic advantage of elimination. Bulky strong bases have difficulty attacking carbon and instead remove a beta hydrogen, especially when heated, thereby favoring E2. 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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