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Questions and Answers
What is a functional group?
A potentially reactive unit within a molecule.
Which of the following are ways functional groups affect drugs? (Select all that apply)
What are substituents?
Groups attached to the basic framework of a molecule.
Some substituents, such as methyl groups, are functional groups.
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A functional group works together as a ______.
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What is tautomerization?
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What are the forms involved in keto-enol tautomerization?
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What does the equilibrium constant in tautomerization depend on?
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The keto form is often favored in the tautomerization of ordinary ketones.
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What is an example of a functional group capable of tautomerization?
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Which effect describes the polarization of a bond formed between atoms of different electronegativities?
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What is a field effect?
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Study Notes
Functional Groups
- A functional group is a reactive unit within a molecule, influencing its properties and behavior.
- Drugs are often multi-functional, featuring various functional groups that can be part of the basic framework or serve as substituents.
- Functional groups are crucial for understanding drug interactions, including:
- Transport mechanisms in the body
- Binding affinity to receptors
- Induction of biological responses
- Metabolism pathways
- Excretion processes
- Stability during storage
- Familiarity with functional groups is essential, with specific knowledge of those listed in relevant figures from educational resources.
Characteristics of Functional Groups
- Functional groups behave collectively and cannot be separated into individual parts.
- Shared electrons across the functional group maintain its integrity, exemplified by:
- An amide remaining an amide, not an amine and ketone.
- A sulfonic acid being distinct from a sulfone and alcohol.
Tautomerization
- Some functional groups can exist in two distinct forms if a neighboring position has at least one hydrogen.
- Tautomerization involves the migration of hydrogen from an adjacent carbon to form a carbonyl oxygen-bonded hydroxyl (O-H).
- Example transformation: A ketone can convert to an enol, characterized by an O-H group adjacent to a double bond.
- Keto and enol forms are in equilibrium, referred to as tautomers, differing by hydrogen attachment and double bond location.
- The stability of tautomers dictates the equilibrium constant; for common ketones, the keto form predominates, while the enol form is favored in specific compounds like acetylacetone due to intramolecular hydrogen bonding.
Types of Tautomerization
- Keto-enol tautomerization is one of the best-known forms, but other types include:
- Imine-enamine tautomerization, favoring the imine form.
- Oxime-nitroso tautomerization, favoring the oxime form.
Electronic Effects
- Bonds formed between atoms of different electronegativities exhibit polarization, affecting charge distribution.
- The inductive effect causes sequential polarization, where electron attraction by the more electronegative atom leads to partial positive charges on adjacent atoms; this effect diminishes with distance.
- Field effects occur when polarization happens through space due to the proximity of electronegative groups, independent of bond connections.
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Description
This quiz covers the concepts of functional groups and their significance in organic chemistry. Learn about how different substituents can affect the reactivity and characteristics of molecules. Test your understanding of the role of functional groups in drug design and molecular structures.
