Textbook Question
Predict the major products of the following reactions.
(b)
21. Aldehydes and Ketones: Nucleophilic Addition
DIBAL
2:17 minutesProblem 8e
Textbook Question
Predict the products of the following reactions.
(e) product of (c) + DIBAL-H, then hydrolysis
Verified step by step guidance1
Step 1: Understand the reaction components. DIBAL-H (Diisobutylaluminum hydride) is a selective reducing agent commonly used in organic chemistry to reduce esters, nitriles, and other carbonyl compounds to aldehydes under controlled conditions. Hydrolysis typically follows the reduction step to complete the reaction.
Step 2: Analyze the product of reaction (c). Identify the functional group(s) present in the compound obtained from reaction (c). This will help determine how DIBAL-H will interact with the molecule.
Step 3: Apply the action of DIBAL-H. If the product of (c) contains an ester group, DIBAL-H will reduce it to an aldehyde. If it contains a nitrile group, DIBAL-H will reduce it to an imine intermediate, which upon hydrolysis will yield an aldehyde. Write the intermediate structure after the reduction step.
Step 4: Perform hydrolysis. After the reduction by DIBAL-H, hydrolysis (typically with water or a dilute acid) will convert any intermediate species (e.g., imines) into the final aldehyde product. Write the structure of the final product after hydrolysis.
Step 5: Verify the product. Ensure that the final product is consistent with the expected reactivity of DIBAL-H and hydrolysis. Double-check the functional groups and connectivity in the molecule to confirm the structure of the product.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
DIBAL-H (Diisobutylaluminum Hydride)
DIBAL-H is a strong reducing agent commonly used in organic chemistry to selectively reduce esters and nitriles to aldehydes. Its ability to provide controlled reduction makes it valuable in synthetic pathways, particularly when a complete reduction to alcohol is not desired. Understanding its reactivity and mechanism is crucial for predicting the products of reactions involving carbonyl compounds.
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Hydrolysis
Hydrolysis is a chemical reaction involving the breakdown of a compound due to reaction with water. In organic chemistry, hydrolysis often refers to the conversion of esters or amides into their corresponding acids and alcohols or amines, respectively. This process is essential for understanding how the products of reductions, such as those involving DIBAL-H, can be further transformed in aqueous conditions.
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Product Prediction in Organic Reactions
Predicting the products of organic reactions involves understanding the functional groups present, the reagents used, and the reaction conditions. This requires knowledge of reaction mechanisms, such as nucleophilic attack and electrophilic addition, which dictate how reactants interact and transform. Mastery of these principles allows chemists to anticipate the outcome of complex reactions, such as those involving DIBAL-H and subsequent hydrolysis.
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