No, polar compounds cannot interact with the hydrophobic tails of phospholipids. This is because the tails are nonpolar and do not interact with remote polar ones.
Image modified from Open Biology. Each phospholipid is amphiphilic, with two hydrophobic tails and one hydrophilic head. The hydrophobic ends point inward toward each other, and the hydrophilic heads point outward.
Hydrophobic molecules are water-repellent as well as the inside of the membrane, so if they are small enough they can easily cross the cell membrane. Small lipids and steroids are hydrophobic and can easily cross membranes.
In some cases, both hydrophilic and hydrophobic properties occur in one molecule of her. Examples of these amphiphilic molecules are the lipids that make up cell membranes. Another example is a soap with a hydrophilic head and a hydrophobic tail that dissolves in both water and oil.
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