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

21. Aldehydes and Ketones: Nucleophilic Addition

Imine vs Enamine

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Imine vs Enamine

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3:08 minutes

Problem 37f

Textbook Question

Draw structures of the following derivatives.
(f) the methyl hemiacetal of formaldehyde

Verified step by step guidance

Step 1: Understand the concept of a hemiacetal. A hemiacetal is formed when an alcohol reacts with an aldehyde. It contains both an -OH group and an -OR group attached to the same carbon atom.

Step 2: Identify the starting material. Formaldehyde (CH₂O) is the simplest aldehyde, consisting of a carbonyl group (C=O) bonded to two hydrogen atoms.

Step 3: Recognize the alcohol involved in the reaction. The problem specifies 'methyl,' which refers to methanol (CH₃OH). Methanol will act as the alcohol in this reaction.

Step 4: Combine formaldehyde and methanol to form the methyl hemiacetal. The oxygen atom of the alcohol attacks the carbonyl carbon of formaldehyde, forming a new C-O bond. The carbonyl oxygen becomes protonated, resulting in an -OH group on the same carbon.

Step 5: Draw the structure of the methyl hemiacetal. The central carbon will have one hydrogen atom, one -OH group, one -OCH₃ group (from methanol), and one bond to the original oxygen from formaldehyde.

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Key Concepts

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

Hemiacetals

Hemiacetals are organic compounds formed from the reaction of an alcohol with an aldehyde or ketone. They contain one hydroxyl group (-OH) and one alkoxy group (-O-R) attached to the same carbon atom, which is the carbonyl carbon of the aldehyde or ketone. Hemiacetals are typically unstable and can further react to form acetals when treated with an excess of alcohol.

Formaldehyde

Formaldehyde is the simplest aldehyde, with the chemical formula CH2O. It is a colorless gas at room temperature and is highly reactive due to the presence of the carbonyl group (C=O). In organic synthesis, formaldehyde is often used as a starting material for the preparation of various derivatives, including hemiacetals and acetals.

Methyl Group

A methyl group is a functional group derived from methane (CH4) and is represented as -CH3. In the context of organic chemistry, the methyl group can influence the reactivity and properties of molecules. When forming a methyl hemiacetal from formaldehyde, the methyl group replaces one of the hydrogen atoms on the carbon atom of the hemiacetal structure, affecting its stability and reactivity.

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