Textbook Question
Within each set of structures, indicate which will react fastest, and which slowest, toward nucleophilic addition in basic conditions.
(c)
13. Alcohols and Carbonyl Compounds
Nucleophilic Addition
2:38 minutesProblem 12b
Textbook Question
Predict the product of the following aldehyde and ketone addition reactions.
(b) 
Verified step by step guidance1
Identify the functional groups present in the reactants. Aldehydes and ketones both contain a carbonyl group (C=O).
Determine the type of addition reaction. Aldehydes and ketones typically undergo nucleophilic addition reactions due to the electrophilic nature of the carbonyl carbon.
Identify the nucleophile in the reaction. Common nucleophiles include hydride ions (H-) from reducing agents or organometallic reagents like Grignard reagents (R-MgX).
Consider the mechanism of the reaction. The nucleophile will attack the electrophilic carbonyl carbon, leading to the formation of a tetrahedral intermediate.
Predict the final product. The addition of the nucleophile to the carbonyl group will result in the formation of an alcohol if the nucleophile is a hydride or an alkoxide if the nucleophile is an organometallic reagent.
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Video duration:
2mKey Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Aldol Condensation
Aldol condensation is a reaction between aldehydes and ketones that involves the formation of a β-hydroxy aldehyde or ketone. This reaction occurs when an enolate ion, generated from a carbonyl compound, attacks another carbonyl carbon, leading to the formation of a new carbon-carbon bond. The product can further dehydrate to yield an α,β-unsaturated carbonyl compound.
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Nucleophilic Addition
Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbon atom in a carbonyl group. This process is crucial in the formation of alcohols, aldehydes, and ketones. Understanding the reactivity of carbonyl compounds and the nature of nucleophiles is essential for predicting the products of reactions involving aldehydes and ketones.
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Reaction Mechanism
A reaction mechanism is a step-by-step description of the pathway taken during a chemical reaction. It outlines the sequence of elementary steps, including bond breaking and forming, that lead to the final products. Analyzing the mechanism helps in predicting the products of reactions involving aldehydes and ketones, as it provides insight into the intermediates and transition states formed during the reaction.
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