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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2:22 minutes

Problem 34c

Textbook Question

Suggest the most appropriate reagent for each synthesis, and explain your choice.
(c)

Verified step by step guidance

Step 1: Analyze the transformation. The starting material is a ketone with a methoxy group (-OCH3) attached to the carbonyl carbon. The product is an alcohol (-CH2OH) where the methoxy group has been replaced by a hydroxymethyl group.

Step 2: Recognize the type of reaction. This transformation involves the reduction of the ester functional group (-COOCH3) to a primary alcohol (-CH2OH). This suggests the use of a reducing agent.

Step 3: Identify the appropriate reagent. Lithium aluminum hydride (LiAlH4) is a strong reducing agent commonly used to reduce esters to primary alcohols. It selectively reduces the ester group without affecting the double bond in the molecule.

Step 4: Explain the mechanism. LiAlH4 donates hydride ions (H-) to the carbonyl carbon of the ester, breaking the C=O bond and forming an intermediate alkoxide. Subsequent protonation during workup converts the alkoxide to the alcohol (-CH2OH).

Step 5: Note reaction conditions. The reaction typically requires an anhydrous solvent like ether and careful handling due to the reactivity of LiAlH4. After reduction, the reaction mixture is quenched with water or an acid to complete the conversion to the alcohol.

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Key Concepts

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

Reagents in Organic Synthesis

Reagents are substances used in chemical reactions to facilitate the transformation of reactants into products. In organic synthesis, the choice of reagent is crucial as it determines the reaction pathway, the functional groups involved, and the overall yield of the desired product. Understanding the properties and reactivity of various reagents is essential for selecting the most appropriate one for a specific synthesis.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Identifying the functional groups present in the starting materials and the desired product is vital for determining which reagents will effectively facilitate the necessary transformations. Knowledge of common functional groups helps predict reactivity and selectivity in organic reactions.

Reaction Mechanisms

A reaction mechanism is a step-by-step description of the process by which reactants are converted into products. Understanding the mechanism provides insight into how and why certain reagents are chosen, as it reveals the intermediates formed and the energy changes involved. This knowledge is essential for predicting the outcomes of reactions and for troubleshooting synthesis problems.

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Related Practice

Textbook Question

Suggest the most appropriate method for each of the following laboratory syntheses. In each case, suggest both a chromium reagent and a chromium-free reagent.

(f) 1-methylcyclohexanol → 2-methylcyclohexanone (several steps)

Textbook Question

Show how you would make each compound, beginning with an alcohol of your choice.

(g)

(h)

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.

Textbook Question

Both NaBH₄ and NaBD₄ are commercially available, and D₂O is common and inexpensive. Show how you would synthesize the following labeled compounds, starting with butan-2-one.

(a)

Textbook Question

Sodium triacetoxyborohydride, NaBH(OAc)₃, is a mild reducing agent that reduces aldehydes much more quickly than ketones. It can be used to reduce aldehydes in the presence of ketones, such as in the following reaction:

(a) Draw a complete Lewis structure for sodium triacetoxyborohydride.

Textbook Question

Draw the products of the following reactions. Indicate whether each reaction is an oxidation or a reduction.

Textbook Question

Propose a mechanism for the following reaction:

Textbook Question

Predict the product of the following reaction sequences.

(c)

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