Predict the major, organic product for the following reaction. <img src="https://media.pearsoncmg.com/ph/esm/ecs_mullins_organic1e/msa/content/practice-test/img/Ch25_Q10_QT.jpg" alt="The figure illustrates a reaction in which the product has to be determined. The reaction contains three reactants. The first reactant has the following structure: A 7-carbon alkane chain is depicted as a line structure using 6 zigzag lines. C 3 is wedge bonded to N H 2 above. C 4 is dash bonded to C H 3 below in the form of a dashed line. C 6 is single bonded to C H 3 below and C H 3 on the lower right, each in the form of a line. The second reactant is C H 3 I (excess) written over the reaction arrow. The third reactants are A g 2 O and H 2 O written under the reaction arrow." />

Table of contents

Skip topic navigation

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

Hofmann Elimination

Struggling with Organic Chemistry?

Join thousands of students who trust us to help them ace their exams!Watch the first video

Multiple Choice

Predict the major, organic product for the following reaction.

The figure illustrates the structure of a molecule. A 6-carbon alkene chain is depicted as a line structure using 5 zigzag lines. A double bond is present between C 1 and C 2. C 1 is single bonded to C H 3 below in the form of a line. C 3 is dash bonded to C H 3 below in the form of a dashed line. C 5 is single bonded to C H 3 below in the form of a line. C 5 is single bonded to C H 3 on the lower right in the form of a line.

The figure illustrates the structure of a molecule. A 7-carbon alkene chain is depicted as a line structure using 6 zigzag lines. A double bond is present between C 3 and C 4. C 4 is single bonded to C H 3 below in the form of a line. C 6 is single bonded to C H 3 below in the form of a line. C 6 is single bonded to C H 3 on the lower right in the form of a line.

The figure illustrates the structure of a molecule. A 5-carbon alkene chain is depicted as a line structure using 4 zigzag lines. A double bond is present between C 3 and C 4. C 4 is single bonded below to C 1 of a 3-carbon alkane chain depicted as a line structure using 2 zigzag lines. C 2 of the 3-carbon alkane chain is single bonded to C H 3 below and C H 3 on the lower right, each in the form of a line.

Next problem

Verified step by step guidance

Identify the starting material: The structure contains an amine group (NH2) attached to a carbon chain with a tertiary butyl group.

Recognize the reagents: The reaction involves CH3I (excess) and Ag2O, H2O. This suggests a Hofmann elimination reaction, where the amine is first converted to a quaternary ammonium salt.

Understand the mechanism: The amine reacts with excess CH3I to form a quaternary ammonium iodide salt. This is a nucleophilic substitution reaction where the nitrogen atom attacks the methyl iodide.

Consider the elimination step: The quaternary ammonium salt is treated with Ag2O and H2O, which facilitates the elimination of the least substituted beta-hydrogen, leading to the formation of an alkene.

Predict the major product: The Hofmann elimination typically results in the formation of the least substituted alkene, due to steric hindrance. Analyze the structure to determine which beta-hydrogen is least hindered and predict the resulting alkene structure.