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Question

Benzoic acid on reacting with lithium aluminium hydride gives

The correct answer is

Benzyl alcohol

Understanding the Reaction of Benzoic Acid with Lithium Aluminium Hydride

The question asks about the product formed when Benzoic acid reacts with lithium aluminium hydride.

Let's first understand the reactants:

  • Benzoic acid: This is a carboxylic acid with the chemical formula $\text{C}_6\text{H}_5\text{COOH}$. It contains a phenyl group attached to a carboxyl group.
  • Lithium aluminium hydride ($\text{LiAlH}_4$): This is a very strong reducing agent commonly used in organic chemistry. It is capable of reducing various functional groups, including carboxylic acids, esters, amides, nitriles, and epoxides.

Reduction of Carboxylic Acids by $\text{LiAlH}_4$

Lithium aluminium hydride is known to reduce carboxylic acids to primary alcohols. The reaction typically involves the hydride ion ($\text{H}^-$) attacking the electrophilic carbonyl carbon, followed by elimination steps and further reduction. The overall process effectively replaces the carbon-oxygen double bond and the $\text{-OH}$ group of the carboxyl group with $\text{-CH}_2\text{-}$.

The general reaction for the reduction of a carboxylic acid ($\text{RCOOH}$) with $\text{LiAlH}_4$ is:

\(\text{RCOOH} \xrightarrow{\text{1. LiAlH}_4, \text{ ether}} \text{RCH}_2\text{OH}\)
\(\phantom{\text{RCOOH}} \xrightarrow{\text{2. H}_2\text{O}}\)

In this reaction, the carboxylic acid is reduced to the corresponding primary alcohol.

Applying the Reaction to Benzoic Acid

When Benzoic acid reacts with lithium aluminium hydride, the carboxyl group ($\text{-COOH}$) attached to the phenyl ring is reduced to a primary alcohol group ($\text{-CH}_2\text{OH}$).

The structure of Benzoic acid is:

\(\text{C}_6\text{H}_5\text{-COOH}\)

The product formed after reduction with $\text{LiAlH}_4$ will be the compound where the $\text{-COOH}$ group is converted to $\text{-CH}_2\text{OH}$. This compound is benzyl alcohol.

The structure of benzyl alcohol is:

\(\text{C}_6\text{H}_5\text{-CH}_2\text{OH}\)

The reaction can be written as:

\(\text{C}_6\text{H}_5\text{COOH} \xrightarrow{\text{1. LiAlH}_4, \text{ ether}} \text{C}_6\text{H}_5\text{CH}_2\text{OH}\)
\(\phantom{\text{C}_6\text{H}_5\text{COOH}} \xrightarrow{\text{2. H}_2\text{O}}\)

Thus, the reaction of Benzoic acid with lithium aluminium hydride yields benzyl alcohol.

Analyzing the Options

Let's look at the given options:

  1. Benzene ($\text{C}_6\text{H}_6$): This is an aromatic hydrocarbon. It is not the product of this reduction reaction.
  2. Benzyl alcohol ($\text{C}_6\text{H}_5\text{CH}_2\text{OH}$): This is a primary alcohol and matches the product we determined from the reduction of Benzoic acid.
  3. Toluene ($\text{C}_6\text{H}_5\text{CH}_3$): This is methylbenzene. It is not the product of this reduction reaction.
  4. None of the above: This would be correct only if none of the above options were the product.

Based on the chemistry of $\text{LiAlH}_4$ reduction of carboxylic acids, the product of the reaction of Benzoic acid is indeed benzyl alcohol.

Reactant Reagent Product Type (from carboxylic acid) Specific Product from Benzoic Acid
Benzoic acid Lithium aluminium hydride ($\text{LiAlH}_4$) Primary Alcohol Benzyl alcohol

In summary, Benzoic acid reacts with lithium aluminium hydride to produce benzyl alcohol through a reduction process.

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Important Questions from Organic Chemistry

  1. Which of the hydrocarbons are arranged as per the increasing order of their boiling points?

  2. Which among the following statements with respect to carbon is/are correct?

    1. Carbon forms the basis for all living organisms and many things we use

    2. Carbon shows tetra-valency and the property of catenation

    3. Carbon forms covalent bonds with itself and other elements

    4. Carbon forms compounds containing triple and tetra bonds between carbon atoms

    Select the correct answer using the code given below:

  3. Which one of the following cell organelles does NOT possess nucleic acid?

  4. Which one of the following is NOT a synthetic detergent?

  5. Which of the following is the chemical name of baking soda?

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