Table of contents

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

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2:19 minutes

Problem 35d,e,f

Textbook Question

Show how you would synthesize each compound, starting with an ester containing no more than eight carbon atoms. Any other necessary reagents may be used.
(d) Ph₂CHOH
(e) PhCH₂OH
(f) PhCOOH

Verified step by step guidance

Step 1: For compound (d) Ph2CHOH (diphenylmethanol), start with an ester containing no more than eight carbons, such as methyl benzoate (C6H5COOCH3). Perform a Grignard reaction by reacting methyl benzoate with phenylmagnesium bromide (PhMgBr) in an ether solvent. This will form a tertiary alcohol intermediate. Hydrolyze the intermediate with water to yield diphenylmethanol.

Step 2: For compound (e) PhCH2OH (benzyl alcohol), start with an ester such as methyl benzoate (C6H5COOCH3). Reduce the ester to the corresponding alcohol using a reducing agent like lithium aluminum hydride (LiAlH4) in an ether solvent. Follow this with an aqueous workup to obtain benzyl alcohol.

Step 3: For compound (f) PhCOOH (benzoic acid), start with an ester such as methyl benzoate (C6H5COOCH3). Perform hydrolysis of the ester using either acidic (H2SO4, H2O) or basic (NaOH, H2O) conditions. If basic hydrolysis is used, the reaction will yield the carboxylate salt, which can be acidified with a strong acid (e.g., HCl) to produce benzoic acid.

Step 4: Ensure that the starting ester contains no more than eight carbons. For all three compounds, methyl benzoate (C6H5COOCH3) is a suitable starting material as it meets this requirement and provides the necessary aromatic ring for the target compounds.

Step 5: Verify the reaction conditions and reagents for each step to ensure the desired transformations occur efficiently. For example, confirm that the Grignard reagent is prepared under anhydrous conditions, and that the reducing agent (LiAlH4) is handled carefully due to its reactivity with water.

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Key Concepts

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

Ester Synthesis

Ester synthesis typically involves the reaction of a carboxylic acid with an alcohol, resulting in the formation of an ester and water. This process, known as esterification, can be catalyzed by an acid to increase the reaction rate. Understanding the structure and reactivity of esters is crucial for synthesizing compounds that contain them as functional groups.

Reduction Reactions

Reduction reactions in organic chemistry involve the gain of electrons or hydrogen, often resulting in the conversion of carbonyl compounds to alcohols. For example, the reduction of an aldehyde or ketone can yield primary or secondary alcohols, respectively. Familiarity with reducing agents, such as lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4), is essential for synthesizing alcohols from carbonyl precursors.

Phenolic Compounds

Phenolic compounds are characterized by the presence of a hydroxyl group (-OH) attached to an aromatic ring. They can be synthesized from various precursors, including phenols and aromatic aldehydes. Understanding the reactivity of phenolic compounds is important for manipulating their structures and creating derivatives, such as alcohols or carboxylic acids, in organic synthesis.

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Related Practice

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.

Textbook Question

In which step(s) of the hydride reduction of an ester does the compound undergo reduction? (Hint: Count the bonds to oxygen.)

Textbook Question

Propose a mechanism for the reduction of octanoyl chloride by lithium aluminum hydride.

Textbook Question

Show how you would synthesize the following alcohol by reducing appropriate carbonyl compound.

(d)

Textbook Question

Show how you would synthesize each compound, starting with an ester containing no more than eight carbon atoms. Any other necessary reagents may be used.

(i) HO–(CH₂)₈–OH

Textbook Question

Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.

(d)

Textbook Question

Show how this 1° alcohol can be made from the following:

(d) a carboxylic acid

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