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The reduction of a carboxylic acid using lithium aluminum hydride will yield what final product? (A) An aldehyde (B) An ester (C) A ketone (D) An alcohol

Short Answer

Expert verified
D - An alcohol

Step by step solution

01

- Identify the Reactants

Determine the reactants involved in the reaction. In this case, the reactant is a carboxylic acid being reduced by lithium aluminum hydride (LiAlH鈧).
02

- Understand LiAlH鈧's Role

LiAlH鈧 is a strong reducing agent. It is known for its ability to reduce carboxylic acids to primary alcohols.
03

- Determine the Product

When a carboxylic acid is reduced by LiAlH鈧, the carboxyl group (鈥揅OOH) is fully reduced. The product of this reaction is a primary alcohol (鈥揅H鈧侽H).
04

- Match with Given Options

Compare the determined product with the given options: (A) An aldehyde, (B) An ester, (C) A ketone, (D) An alcohol. The correct match is (D) An alcohol.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Lithium Aluminum Hydride
Lithium aluminum hydride, often abbreviated as LiAlH鈧, is a very powerful reagent used in organic chemistry for reductions. It is particularly known for its ability to reduce various functional groups, including carboxylic acids, esters, and ketones. This reduction process usually involves adding hydrogen atoms to the functional group.

LiAlH鈧 is highly reactive and must be handled under anhydrous (water-free) conditions because it will react violently with water. This makes it crucial to perform reactions using LiAlH鈧 in special non-aqueous solvents like diethyl ether or tetrahydrofuran (THF).

In the context of reducing a carboxylic acid, LiAlH鈧 adds hydrogen atoms to the carboxyl group (鈥揅OOH), breaking the double bond between the carbon and the oxygen atoms to yield a primary alcohol (鈥揅H鈧侽H).
Strong Reducing Agent
A reducing agent is a substance that donates electrons to another compound and, in the process, becomes oxidized. Lithium aluminum hydride is considered one of the strongest reducing agents in organic chemistry. This is because it is capable of providing a large amount of hydrogen ions (H鈦), which facilitate the reduction process.

The strength of a reducing agent can often be measured by its ability to reduce various functional groups. For instance, while some reducing agents may only reduce ketones and aldehydes, LiAlH鈧 is powerful enough to reduce a carboxylic acid to an alcohol directly. This makes it a versatile and valuable reagent in synthetic organic chemistry.

Its strong reducing properties mean that reactions involving LiAlH鈧 should be carried out with care. Reactions are typically performed under strictly controlled conditions to ensure safety and the desired outcome.
Primary Alcohol
Primary alcohols are a type of organic compound characterized by the presence of a hydroxyl group (鈥揙H) attached to a primary carbon atom. A primary carbon is a carbon atom that is bonded to only one other carbon atom or no other carbon atoms if it's part of a methyl group.

When a carboxylic acid is reduced using lithium aluminum hydride, the carboxyl group (鈥揅OOH) loses its double bond with the oxygen atom and gains hydrogen atoms, transforming into a primary alcohol. For example, the reduction of acetic acid (CH鈧僀OOH) by LiAlH鈧 yields ethanol (CH鈧僀H鈧侽H) as the final product.

The reduction process involves several steps: the initial addition of a hydride ion (H鈦) from the LiAlH鈧 to the carbonyl carbon of the carboxylic acid, followed by the eventual replacement of the oxygen atom with hydrogen atoms. This makes the process highly efficient, allowing chemists to convert carboxylic acids into primary alcohols effectively.

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