A student, when solving the following 'predict-the-product' question, made a common mistake by writing the answer shown here. Explain why this reaction would not work as written.

Classify the following nucleophiles as strong, weak, or intermediate. Would you expect each to add to a carbonyl directly or wait for a carbocation to form?
b) 
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비슷한 문제에 대한 검증된 영상 답변:
주요 개념
Nucleophilicity
Carbonyl Chemistry
Carbocation Stability
Identify the bonds broken and formed in the following addition reaction.
(a) Would you expect this reaction to be favored based on entropy?
(b) Based on enthalpy [qualitatively]?
(c) Overall?
Another way the preceding might be presented is to say that the minor resonance structure(s) reveal the reactivity of a molecule. Show how the minor resonance structure(s) can help us understand that the following reactions occur with the regioselectivity shown.
(a)
(b)
(c)
Classify the following nucleophiles as strong, weak, or intermediate. Would you expect each to add to a carbonyl directly or wait for a carbocation to form?
(d)
Suggest an acetylide ion and a carbonyl that might be used to make the following products.
(a) oct-4-yn-3-ol
Classify the following nucleophiles as strong, weak, or intermediate. Would you expect each to add to a carbonyl directly or wait for a carbocation to form?
(a)
