What products are obtained from the reaction of the following compounds with LiAlH 4 followed by treatment with dilute acid? c. methyl benzoate d. pentanoic acid

Hello everyone. Today, we have the following problem. Consider the compounds below provide the organic compounds. If the compounds, the products, if the compounds are reacted with lithium aluminum hydride followed by dilute acid. So for our first reaction, we have our prop benzoate, which has the following structure, we have our benzene ring, which is essentially and then we have additional our carbon carbon and an oxygen which is represented by the 08 portion and that carbon or that oxygen is bound to a propal group. And when this is reacted with our lithium aluminum hydride, which is a strong reducing agent. And our dilute acid, which may be sulfuric acid, what we have is we have the reduction of this ether into two alcohols. So we need to cleave the bond between the carbel group and the oxygen and the alky group. Such that we form two alcohols wherein one is derived from that ail portion and the other is derived from the alki group. And we would do the same for the second reaction where we have the following structure, five methyl Hexon OIC acid. So we have the methyl group on carbon five. And when we react this in similar conditions with our dilute acid, we will reduce that carboxylic acid. But this time, we will reduce it into a primary alcohol. And with that, we have solved the problem overall, I hope it helped. And until next time.

Table of contents

Skip topic navigation

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

13. Alcohols and Carbonyl Compounds

Reducing Agent

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Reducing Agent

Previous problemNext problem

4:07 minutes

Problem 21c,d

Textbook Question

What products are obtained from the reaction of the following compounds with LiAlH₄ followed by treatment with dilute acid?
c. methyl benzoate
d. pentanoic acid

Verified step by step guidance

Step 1: Understand the role of LiAlH4 (Lithium Aluminum Hydride). LiAlH4 is a strong reducing agent commonly used to reduce esters, carboxylic acids, aldehydes, and ketones to their corresponding alcohols. The reaction typically involves two steps: reduction with LiAlH4 and subsequent hydrolysis with dilute acid to complete the reaction.

Step 2: Analyze the structure of methyl benzoate. Methyl benzoate is an ester with the formula C6H5COOCH3. When treated with LiAlH4, the ester bond is reduced to form two alcohols: the alcohol derived from the carboxylic acid portion (benzyl alcohol, C6H5CH2OH) and the alcohol derived from the alkyl group (methanol, CH3OH).

Step 3: Analyze the structure of pentanoic acid. Pentanoic acid is a carboxylic acid with the formula CH3(CH2)3COOH. When treated with LiAlH4, the carboxylic acid group (-COOH) is reduced to a primary alcohol (-CH2OH). The product is 1-pentanol (CH3(CH2)3CH2OH).

Step 4: Perform the hydrolysis step. After the reduction with LiAlH4, the reaction mixture is treated with dilute acid (e.g., H3O+). This step ensures the protonation of the oxygen atoms and completes the formation of the alcohol products.

Step 5: Summarize the products. For methyl benzoate, the products are benzyl alcohol (C6H5CH2OH) and methanol (CH3OH). For pentanoic acid, the product is 1-pentanol (CH3(CH2)3CH2OH).

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Reduction Reactions

Reduction reactions involve the gain of electrons or the decrease in oxidation state of a molecule. In organic chemistry, this often refers to the conversion of carbonyl compounds (like esters and carboxylic acids) to alcohols. Lithium aluminum hydride (LiAlH4) is a strong reducing agent that can effectively reduce esters and acids to their corresponding alcohols.

LiAlH4 as a Reducing Agent

Lithium aluminum hydride (LiAlH4) is a powerful reducing agent used in organic synthesis. It can reduce a variety of functional groups, including esters, carboxylic acids, and aldehydes, to alcohols. The reaction typically requires anhydrous conditions, and after reduction, the addition of dilute acid is necessary to protonate the alkoxide intermediate formed during the reaction.

Acid-Base Workup

An acid-base workup is a common procedure following a reduction reaction to neutralize any remaining reducing agent and to protonate the alkoxide intermediates. In this context, treating the reaction mixture with dilute acid after the reduction with LiAlH4 converts the alkoxide into the corresponding alcohol, facilitating the isolation of the desired product.

Watch next

Master Reducing Agents with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

Predict the product of the following reductions.

(c)

Textbook Question

How would you reduce the alkene in the presence of a carboxylic acid?

Textbook Question

What alcohols are obtained from the reduction of the following compounds with sodium borohydride?

a. 2-methylpropanal

b. cyclohexanone

Textbook Question

What alcohols are obtained from the reduction of the following compounds with sodium borohydride?

c. 4-tert-butylcyclohexanone

d. acetophenone

Textbook Question

What amides would you react with LiAlH₄ to form the following amines?

a. benzylmethylamine

b. ethylamine

c. diethylamine

d. triethylamine

Textbook Question

An unknown alcohol with a molecular formula of C₇H₁₄O was oxidized to an aldehyde with HOCl. When an acidic solution of the alcohol was distilled, two alkenes were obtained. The alkene formed in greater yield was determined to be 1-methylcyclohexene. The other alkene formed the original un-known alcohol when treated with BH₃/THF followed by H₂O₂, HO^-, and H₂O. Identify the unknown alcohol.

Textbook Question

Compounds containing deuterium (D = ²H) are useful for kinetic studies and metabolic studies with new pharmaceuticals. One way to introduce deuterium is by using the reagent LiAlD₄, equivalent in reactivity to LiAlH₄. Show how to make these deuterium-labeled compounds, using LiAlD₄ and D₂O as your sources of deuterium, and any non-deuterated starting materials you wish.

(b) CH₃CD₂OH

Textbook Question

When LiAlH₄ reduces 3-methylcyclopentanone, the product mixture contains 60% cis-3-methylcyclopentanol and 40% trans-3-methylcyclopentanol. Use your models, and make three-dimensional drawings to explain this preference for the cis isomer.

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap

What products are obtained from the reaction of the following compounds with LiAlH4 followed by treatment with dilute acid?c. methyl benzoated. pentanoic acid

Key Concepts

Reduction Reactions

LiAlH4 as a Reducing Agent

Acid-Base Workup

Watch next

What products are obtained from the reaction of the following compounds with LiAlH₄ followed by treatment with dilute acid?
c. methyl benzoate
d. pentanoic acid