Order of basicity and lipophilicity in organic compounds

In summary, the conversation discusses ranking compounds in order of basicity and lipophilicity. The order of basicity is trimethylamine > 4-methylamine > aniline > 4-nitroaniline > tetramethylammonium chloride > acetanilide, while the order of lipophilicity is n-butanol > 2-butanol > butyl chloride > n-butyl acetate > butyl hydrogen sulphate. The student is asking for clarification and assistance in determining the ionization and lipophilicity of these compounds at different pH levels.
  • #1

MrJason123

2
0
Hello,

I want to rank the following compounds in order of basicity:
trimethylamine, tetramethylammonium chloride, 4-nitroaniline, aniline, acetanilide, 4-methylaniline.
I think this is the order, but I'm not sure for the last ones.
trimethylamine > 4-methylamine > aniline > 4-nitroaniline > tetramethylammonium chloride > acetanilide
Also what happens to their ionization and lipophilicity in pH=2 and pH=10?

And I want to rank these compounds in order of lipophilicity:
n-butanol, 2-butanol, butyl chloride, n-butyl acetate, butyl hydrogen sulphate

Can someone help me?
 
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  • #2
MrJason123 said:
Hello,

I want to rank the following compounds in order of basicity:
trimethylamine, tetramethylammonium chloride, 4-nitroaniline, aniline, acetanilide, 4-methylaniline.
I think this is the order, but I'm not sure for the last ones.
trimethylamine > 4-methylamine > aniline > 4-nitroaniline > tetramethylammonium chloride > acetanilide
Also what happens to their ionization and lipophilicity in pH=2 and pH=10?

And I want to rank these compounds in order of lipophilicity:
n-butanol, 2-butanol, butyl chloride, n-butyl acetate, butyl hydrogen sulphate

Can someone help me?
Welcome to the PF.

Is this for schoolwork?
 
  • #3
No. I'm a student in University and I want to be sure about the answers in theses questions.
 
  • #4
Since it is for schoolwork, it needs to be posted in the Homework Help section of the PF, and you need to fill out the Homework Help Template that you are provided there. That includes the sections on the Relevant Equations/Concepts, and your Attempt at the Solution.

Please re-post in the Homework Help, Chemistry forum. Thank you.
 

What is the relationship between basicity and lipophilicity in organic compounds?

Basicity refers to the ability of a compound to accept a proton or donate an electron pair. Lipophilicity, on the other hand, refers to the tendency of a compound to dissolve in nonpolar solvents. In general, compounds with higher basicity tend to have higher lipophilicity. This is because basic compounds often have polar functional groups, which allow them to interact with nonpolar solvents through dipole-dipole interactions.

How does the structure of an organic compound affect its basicity and lipophilicity?

The basicity and lipophilicity of an organic compound are largely determined by its functional groups and overall molecular structure. For example, compounds with multiple polar functional groups, such as amines and carboxylic acids, tend to have higher basicity and lipophilicity than compounds with only one polar functional group. Additionally, the size and shape of the molecule can also impact its lipophilicity, with more compact molecules being more lipophilic than larger, bulkier molecules.

Can the basicity and lipophilicity of a compound be predicted based on its chemical formula?

While there are some general trends that can be observed, it is not possible to accurately predict the basicity and lipophilicity of a compound based solely on its chemical formula. This is because the structure and arrangement of atoms within a molecule can greatly influence its properties, and these factors cannot be determined from a chemical formula alone.

How do basicity and lipophilicity affect the reactivity of organic compounds?

Organic compounds with higher basicity and lipophilicity tend to be more reactive than those with lower values. This is because these compounds are more likely to participate in various chemical reactions due to their ability to interact with other molecules and solvents. However, it is important to note that reactivity is also influenced by other factors such as steric hindrance and electronic effects.

What are some common methods for determining the basicity and lipophilicity of organic compounds?

There are several experimental techniques that can be used to measure the basicity and lipophilicity of organic compounds. These include acid-base titrations, measurement of partition coefficients, and chromatography techniques such as thin-layer chromatography (TLC) and high-performance liquid chromatography (HPLC). Additionally, computational methods such as quantum chemical calculations can also be used to predict the basicity and lipophilicity of compounds.

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