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CHE 008B A01 SS1 2025 Lecture 9 - Aldol Condensation Reagents

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Look at each of the given compounds and determine if they would be a nucleophile only, an electrophile only, both, or neither for an aldol condensation. Compound A: electrophile only Compound B: nucleophile only Compound C: both an electrophile and a nucleophile Compound D: neither Compound E: both an electrophile and a nucleophile Compound F: nucleophile only

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To tackle this question, recall how aldol condensations proceed in terms of electrophile and nucleophile roles. Key concepts to keep in mind: - Electrophile: the carbonyl carbon of an aldehyde or ketone is typically the electrophilic center that accepts nucleophilic attack. - Nucleophile: the enol or enolate form of a carbonyl compound (or another suitably acidic site) can attack an electrophile; in aldol chemistry, the enolate/enol acts as the nucleophile that attacks the carbonyl carbon of another molecule. - A molecule can sometimes act as both electrophile and nucleophile, depending on the reaction partner and whether an enolate/enol is formed at its alpha position. - A molecule that lacks an alpha-hydrogen (and cannot form an enolate/enol) generally behaves as an electrophile (it can be attacked) but not as a nucleoph......Login to view full explanation

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