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

7. Substitution Reactions

Substitution Comparison

Organic Chemistry

7. Substitution Reactions

Substitution Comparison

Previous problemNext problem

3:36 minutes

Problem 81

Textbook Question

Alkylbenzyldimethyl ammonium chloride is a leave-on skin antiseptic used to treat such things as cuts and cold sores. It is also the antiseptic in many hand sanitizers. It is actually a mixture of compounds that differ in the number of carbons (any even number between 8 and 18) in the alkyl group. Show three different sets of reagents (each set composed of an alkyl chloride and an amine) that can be used to synthesize the alkylbenzyldimethyl ammonium chloride shown here.

Verified step by step guidance

Step 1: Identify the structure of the target compound, alkylbenzyldimethyl ammonium chloride. It consists of a benzyl group attached to a nitrogen atom, which is further bonded to two methyl groups and an alkyl chain (with an even number of carbons between 8 and 18). The nitrogen carries a positive charge, and the chloride ion is the counterion.

Step 2: Understand the synthesis mechanism. The target compound can be synthesized via a nucleophilic substitution reaction (SN2) where an alkyl chloride reacts with a tertiary amine. The tertiary amine must contain a benzyl group and two methyl groups to form the desired quaternary ammonium salt.

Step 3: Select the alkyl chloride. Choose three different alkyl chlorides with even numbers of carbons in the alkyl chain (e.g., octyl chloride, decyl chloride, and dodecyl chloride). These will provide the varying alkyl groups in the final product.

Step 4: Select the amine. Use benzyl dimethyl amine as the amine reagent in all three cases. This amine contains the benzyl group and two methyl groups required for the quaternary ammonium structure.

Step 5: Combine the reagents. For each set of reagents, react the chosen alkyl chloride with benzyl dimethyl amine under appropriate conditions (e.g., heating in a polar solvent) to form the desired alkylbenzyldimethyl ammonium chloride. Ensure the reaction proceeds via SN2 to achieve the quaternary ammonium salt.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Quaternary Ammonium Compounds

Quaternary ammonium compounds are a class of chemicals that consist of a positively charged nitrogen atom bonded to four organic groups. In the context of the question, alkylbenzyldimethyl ammonium chloride is a quaternary ammonium compound where the nitrogen is bonded to two methyl groups, a benzyl group, and an alkyl group. These compounds are known for their antimicrobial properties and are commonly used in antiseptics and disinfectants.

Alkyl Halides

Alkyl halides are organic compounds containing a carbon chain bonded to a halogen atom (such as chlorine, bromine, or iodine). In the synthesis of alkylbenzyldimethyl ammonium chloride, alkyl chlorides serve as the source of the alkyl group. The reactivity of alkyl halides allows them to participate in nucleophilic substitution reactions, which are essential for forming the desired quaternary ammonium compound.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group in a molecule by a nucleophile. In this case, the amine acts as the nucleophile that attacks the alkyl halide, leading to the formation of an intermediate that can further react to yield the quaternary ammonium compound. Understanding the mechanisms of these reactions, such as SN1 and SN2 pathways, is crucial for predicting the outcomes of the synthesis described in the question.

Watch next

Master How do we predict if the mechanism is SN1 or SN2? with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

Show how you might use S_N2 reactions to convert 1-chlorobutane into the following compounds.

b. 1-fluorobutane

Textbook Question

A solution of pure (S)-2-iodobutane ([α] = +15.90°) in acetone is allowed to react with radioactive iodide, ¹³¹I^–, until 1.0% of the iodobutane contains radioactive iodine. The specific rotation of this recovered iodobutane is found to be +15.58°.

b. What does this result suggest about the mechanism of the reaction of 2-iodobutane with iodide ion?

Textbook Question

Show how you would convert (in one or two steps) 1-phenylpropane to the three products shown below. In each case, explain what unwanted reactions might produce undesirable impurities in the product.

Textbook Question

Using cyclohexane as one of your starting materials, show how you would synthesize the following compounds.

(c)

Textbook Question

Which reaction in each of the following pairs takes place more rapidly? (EtOH is ethyl alcohol; Et₂O is diethyl ether.)

Textbook Question

Under which of the following reaction conditions will (R)-1-chloro-1-phenylethane form the most (R)-1-phenyl-1-ethanol: in water or in 1.0 M HO⁻?

Textbook Question

Draw the substitution products for each of the following reactions; if the products can exist as stereoisomers, show what stereoisomers are obtained:

e. 1-bromo-2-butene + CH₃O⁻

f. 1-bromo-2-butene + CH₃OH

Textbook Question

Suggest a reagent to carry out each of the following conversions to an alcohol.

(a)

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap