교과서 질문
What is the specific rotation of an equilibrium mixture of fructose? (Hint: Recall that the specific rotation of an equilibrium mixture of glucose is +52.7.)
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21. Aldehydes and Ketones: Nucleophilic Addition
Imine vs Enamine
객관식
Predict the major, organic product for the following reaction.
A
B
C
D
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검증된 단계별 안내1
Identify the functional groups in the reactants: The starting material is an aromatic ketone with a methoxy group on the benzene ring and a propanone side chain. The reagent is cyclopentylamine, which is a primary amine.
Recognize the type of reaction: This is a nucleophilic addition-elimination reaction, commonly known as an amine addition to a carbonyl group, forming an imine or enamine.
Determine the mechanism: The lone pair of electrons on the nitrogen atom of the amine attacks the electrophilic carbon of the carbonyl group, forming a tetrahedral intermediate.
Consider the elimination step: The intermediate collapses, expelling a molecule of water and forming a double bond between the nitrogen and the carbon, resulting in an imine or enamine.
Predict the major product: Given the structure of the starting material and the reagent, the major product is likely to be an enamine, where the nitrogen is bonded to the carbon adjacent to the aromatic ring, and the double bond is between the nitrogen and the carbon of the former carbonyl group.
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