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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7:14 minutes

Problem 58a,b,c

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the first reaction. The reagent Na in liquid NH₃ is used for the partial reduction of alkynes to trans-alkenes. This reaction is stereospecific and results in the formation of a trans-alkene. Identify the alkyne in the starting material and predict the trans-alkene product.

Step 2: For the second reaction, LiAlH₄ is a strong reducing agent that reduces amides to amines. The carbonyl group (C=O) in the amide will be reduced, and the resulting product will be an amine. Write the structure of the amine product by replacing the carbonyl group with a CH₂ group.

Step 3: Examine the third reaction. The reagent H₂ with Pd/C is used for catalytic hydrogenation. This reaction reduces alkenes to alkanes by adding hydrogen across the double bond. Identify the alkene in the starting material and predict the alkane product.

Step 4: Determine whether each reaction is an oxidation or a reduction. Reduction involves the gain of hydrogen or loss of oxygen, while oxidation involves the loss of hydrogen or gain of oxygen. Based on the reagents and products, classify each reaction accordingly.

Step 5: Draw the products for each reaction, ensuring the stereochemistry and functional group changes are accurately represented. Label each product with its corresponding reaction type (oxidation or reduction).

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Key Concepts

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

Oxidation and Reduction

Oxidation and reduction are fundamental concepts in organic chemistry that describe the transfer of electrons between species. Oxidation involves the loss of electrons or an increase in oxidation state, while reduction involves the gain of electrons or a decrease in oxidation state. Understanding these processes is crucial for predicting the products of chemical reactions.

Reaction Mechanisms

Reaction mechanisms detail the step-by-step sequence of events that occur during a chemical reaction. They provide insight into how reactants transform into products, including the breaking and forming of bonds. Familiarity with common mechanisms, such as nucleophilic substitution or elimination, is essential for accurately drawing reaction products.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing functional groups is vital for predicting how different compounds will react in oxidation or reduction processes. Examples include alcohols, aldehydes, and ketones, each exhibiting unique reactivity patterns.

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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.

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

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

(c)

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

Propose a mechanism for the following reaction:

Textbook Question

Predict the product of the following reaction sequences.

(c)

Textbook Question

Show how you would synthesize the following compounds from the appropriate carboxylic acids or acid derivatives.

Textbook Question

How can the following compounds be prepared from the given starting materials?

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