Ch. 21 - Carboxylic Acid Derivatives

Wade9th EditionOrganic ChemistryISBN: 9780135213728Non è quello che usi tu?Cambia libro di testo

Wade 9th Edition

Ch. 21 - Carboxylic Acid Derivatives

Problema 50k

Capitolo 21, Problema 50k

Predict the products of the following reactions.
(k)

Guida verificata passo dopo passo

Step 1: Identify the functional groups in the given compound. The molecule contains a benzyl group (PhCH2), a secondary alcohol (CH3-CH), and an amide group (C=O-NH2).

Step 2: Recognize the reagent used in the reaction. Lithium aluminum hydride (LiAlH4) is a strong reducing agent that can reduce amides to amines and other carbonyl compounds to alcohols.

Step 3: Predict the reduction of the amide group. The amide group (C=O-NH2) will be reduced to a primary amine (-CH2-NH2) by LiAlH4.

Step 4: Consider the reduction of other carbonyl groups. If there were any aldehydes or ketones present, they would also be reduced to alcohols. However, in this molecule, the amide is the primary target for reduction.

Step 5: Write the final structure after reduction. The benzyl group (PhCH2) and the secondary alcohol (CH3-CH) remain unchanged, while the amide group is converted to a primary amine (-CH2-NH2).

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Reduction Reactions

Reduction reactions involve the gain of electrons or the decrease in oxidation state by a molecule. In organic chemistry, this often refers to the conversion of carbonyl compounds (like ketones and aldehydes) to alcohols. Lithium aluminum hydride (LiAlH4) is a strong reducing agent commonly used to reduce carbonyl groups to alcohols.

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Reductive Amination

Lithium Aluminum Hydride (LiAlH4)

LiAlH4 is a powerful reducing agent used in organic synthesis. It can reduce a variety of functional groups, including esters, carboxylic acids, and amides, to their corresponding alcohols. In the given reaction, excess LiAlH4 will reduce the amide group to an amine and the carbonyl group to an alcohol, showcasing its versatility in functional group transformations.

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Why LiAlH4 doesn't work

Hydrolysis of Alkoxides

After reduction with LiAlH4, the resulting alkoxide must be hydrolyzed to yield the final alcohol and amine products. This is typically done by adding water (H2O) to the reaction mixture, which reacts with the alkoxide to form the corresponding alcohol and release the aluminum salts. This step is crucial for completing the transformation and obtaining the desired products.

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Percorso guidato

3:09

Hydrolysis of Thioesters Example 2

Pratica correlata

Domanda del libro di testo

Phosgene is the acid chloride of carbonic acid. Although phosgene was used as a war gas in World War I, it is now used as a reagent for the synthesis of many useful products. Phosgene reacts like other acid chlorides, but it can react twice.

(b) Predict the products formed when phosgene reacts with 1 equivalent of methanol, followed by 1 equivalent of aniline.

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Domanda del libro di testo

Predict the products of the following reactions.

(j)

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Domanda del libro di testo

(a) Predict the products formed when phosgene reacts with excess propan-2-ol.

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