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

Organometallic Cumulative Practice

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

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7:12 minutes

Problem 38a

Textbook Question

Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than two carbons, indicate how each of the following compounds can be prepared:
a.

Verified step by step guidance

Step 1: Begin with the given starting material, 1-bromobutane. The goal is to convert this alkyl halide into the desired aldehyde product.

Step 2: Perform a nucleophilic substitution reaction to replace the bromine atom with a cyanide group. Use sodium cyanide (NaCN) as the nucleophile in an SN2 reaction. This will yield butanenitrile (CH3CH2CH2CN).

Step 3: Hydrolyze the nitrile group to form a carboxylic acid. Use acidic hydrolysis (e.g., H2SO4 and water) to convert the nitrile group (-CN) into a carboxylic acid (-COOH), resulting in butanoic acid.

Step 4: Reduce the carboxylic acid to an aldehyde. Use a selective reducing agent such as diisobutylaluminum hydride (DIBAL-H) at low temperatures to stop the reduction at the aldehyde stage, yielding butanal.

Step 5: Confirm the structure of the final product, butanal, which matches the desired compound shown in the image.

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Key Concepts

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

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophilic carbon atom, replacing a leaving group. In this case, the alkyl bromide serves as the substrate, and the bromine atom acts as the leaving group. Understanding this mechanism is crucial for predicting the products formed when the alkyl bromide reacts with a nucleophile, such as an alcohol or a carbonyl compound.

Carbonyl Compounds

Carbonyl compounds, characterized by the presence of a carbon-oxygen double bond (C=O), play a significant role in organic synthesis. They can undergo various reactions, including nucleophilic addition, where a nucleophile attacks the carbon atom of the carbonyl group. In the context of the question, the carbonyl compound is likely involved in the transformation of the alkyl bromide to an alcohol, highlighting the importance of understanding carbonyl reactivity.

Reduction Reactions

Reduction reactions involve the gain of electrons or hydrogen, leading to a decrease in oxidation state. In organic chemistry, this often refers to the conversion of carbonyl compounds to alcohols. The reaction depicted in the image suggests that the alkyl bromide is being transformed into an alcohol, which typically requires a reducing agent. Familiarity with common reducing agents and their mechanisms is essential for successfully completing the synthesis outlined in the question.

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Textbook Question

Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than three carbons, indicate how each of the following compounds can be prepared:

Textbook Question

The Reformatsky reaction is an addition reaction in which an organozinc reagent is used instead of a Grignard reagent to add to the carbonyl group of an aldehyde or a ketone. Because the organozinc reagent is less reactive than a Grignard reagent, a nucleophilic addition to the ester group does not occur.

The organozinc reagent is prepared by treating an α-bromo ester with zinc.

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Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than two carbons, indicate how each of the following compounds can be prepared:

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Using the given starting material, any necessary inorganic reagents, and any carbon-containing compounds with no more than two carbons, indicate how each of the following compounds can be prepared:

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