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

26. Amines

Amine Alkylation

Organic Chemistry

26. Amines

Amine Alkylation

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2:18 minutes

Problem 29c

Textbook Question

Predict the products of the following reactions.
(c)

Verified step by step guidance

Step 1: Identify the reactants. Lys refers to lysine, an amino acid with an amine group (-NH2) and a carboxylic acid group (-COOH), along with an additional amine group in its side chain. (CH3CO)2O is acetic anhydride, a reagent commonly used for acetylation reactions.

Step 2: Understand the reaction conditions. The presence of excess acetic anhydride suggests that all nucleophilic groups in lysine will react with acetic anhydride to form acetylated products.

Step 3: Determine the reactive sites in lysine. The primary amine group (-NH2) in the side chain and the alpha-amino group (-NH2) attached to the alpha carbon are both nucleophilic and can react with acetic anhydride. Additionally, the hydroxyl group (-OH) of the carboxylic acid can also react.

Step 4: Predict the products. Each amine group will react with acetic anhydride to form an amide bond, resulting in acetylation. The hydroxyl group of the carboxylic acid will react to form an ester bond. The final product will be a fully acetylated lysine derivative.

Step 5: Write the general structure of the product. The alpha-amino group and the side chain amine group will each have an acetyl group (-COCH3) attached, and the carboxylic acid group will be converted into an ester (-COOCH3).

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Key Concepts

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

Reaction Mechanisms

Understanding reaction mechanisms is crucial in organic chemistry as they describe the step-by-step process by which reactants transform into products. This includes identifying intermediates, transition states, and the movement of electrons. Familiarity with mechanisms helps predict the outcome of reactions and the stability of products formed.

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 allows chemists to predict how different compounds will react under various conditions. This knowledge is essential for determining the products of organic reactions.

Stereochemistry

Stereochemistry involves the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. It is important for predicting the products of reactions, especially in cases where chirality or geometric isomerism is involved. Understanding stereochemical principles helps in anticipating the specific isomers that may be formed in a reaction.

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Related Practice

Textbook Question

The following drugs are synthesized using the methods in this chapter and in previous chapters. Devise a synthesis for each, starting with any compounds containing no more than six carbon atoms.

(c) Dopamine, one of the neurotransmitters in the brain. Parkinson’s disease is thought to result from a dopamine deficiency.

Textbook Question

The ribonucleosides that make up ribonucleic acid (RNA) are composed of D-ribose (a sugar) and four heterocyclic “bases.” The general structure of a ribonucleoside is shown here.

The four heterocyclic bases are cytosine, uracil, guanine, and adenine. Cytosine and uracil are called pyrimidine bases because their structures resemble pyrimidine. Guanine and adenine are called purine bases because their structures resemble purine.

b. Predict which nitrogen atoms are basic.

Textbook Question

Show how you would use direct alkylation to synthesize the following compounds.

(a) benzyltrimethylammonium iodide

(b) pentan-1-amine

Textbook Question

Which of the following compounds are capable of being resolved into enantiomers?

(d) 1,2,2-trimethylaziridine

(e)

(f)

Textbook Question

Show why p-nitroaniline is a much weaker base (3 pK_b units weaker) than aniline.

Textbook Question

The following drugs are synthesized using the methods in this chapter and in previous chapters. Devise a synthesis for each, starting with any compounds containing no more than six carbon atoms.

(a) Phenacetin, used with aspirin and caffeine in pain-relief medications.

Textbook Question

The following drugs are synthesized using the methods in this chapter and in previous chapters. Devise a synthesis for each, starting with any compounds containing no more than six carbon atoms.

(b) Methamphetamine, once considered a safe diet pill, but now known to be addictive and destructive to brain tissue.

Textbook Question

Basicity depends on availability of an electron pair to bond a proton. Correlate structural effects in these amines with their basicities.

(a) Explain this order:

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