Textbook Question
Solving the following road-map problem depends on determining the structure of A, the key intermediate. Give structures for compounds A through K.
21. Aldehydes and Ketones: Nucleophilic Addition
Imine vs Enamine
3:02 minutesProblem 53c
Textbook Question
Predict the products formed when cyclohexanone reacts with the following reagents.
(c) hydroxylamine and weak acid
Verified step by step guidance1
Identify the functional group in cyclohexanone. Cyclohexanone is a ketone, which contains a carbonyl group (C=O) attached to a six-membered cyclohexane ring.
Understand the role of hydroxylamine (NH2OH). Hydroxylamine is a nucleophile that reacts with carbonyl compounds to form oximes. This reaction typically occurs in the presence of a weak acid, which helps to protonate the carbonyl oxygen and make the carbonyl carbon more electrophilic.
Protonate the carbonyl oxygen of cyclohexanone using the weak acid. This step increases the electrophilicity of the carbonyl carbon, making it more susceptible to nucleophilic attack by hydroxylamine.
Perform the nucleophilic attack. The lone pair of electrons on the nitrogen atom of hydroxylamine attacks the electrophilic carbonyl carbon, forming a tetrahedral intermediate.
Eliminate water (H2O) from the intermediate to form the final product. The result is an oxime, specifically cyclohexanone oxime, where the carbonyl group is replaced by a C=N-OH functional group.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Addition
Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbon atom, typically found in carbonyl compounds like ketones and aldehydes. In the case of cyclohexanone, the carbonyl carbon is susceptible to attack by nucleophiles such as hydroxylamine, leading to the formation of an intermediate that can further react to yield a product.
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Nucleophilic Addition
Hydroxylamine
Hydroxylamine (NH2OH) is a nucleophilic reagent commonly used to convert carbonyl compounds into oximes. When cyclohexanone reacts with hydroxylamine in the presence of a weak acid, the hydroxylamine attacks the carbonyl carbon, resulting in the formation of a cyclohexanone oxime, which is characterized by the presence of the C=N-OH functional group.
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Weak Acid Catalysis
Weak acid catalysis involves the use of a weak acid to facilitate a reaction without significantly altering the pH of the solution. In the reaction of cyclohexanone with hydroxylamine, a weak acid can help protonate the hydroxylamine, enhancing its nucleophilicity and promoting the formation of the oxime product. This catalytic effect can improve the reaction rate and yield.
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