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Alpha Carbon: Acidity & Reactions

Chapter 5 /  Lesson 16

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Instructor: Laura Foist

Laura has a Masters of Science in Food Science and Human Nutrition and has
taught college Science.

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In this lesson we will learn about the alpha carbon. We will learn what the alpha
carbon is and what makes it more acidic than other carbons, and we will see
some reactions in which the alpha carbon participates.

Alpha Carbon
We frequently use the word 'alpha' to mean the strongest, best, or first. We can
use the same logic for remembering what an alpha carbon is. The alpha
carbon is the carbon that is next to a functional group, so we can think of it as
the first carbon to come after the functional group. A functional group is just
any specifically classified group of atoms. Some common examples of functional
groups are alcohols, ketones, aldehydes, halides, alkenes, and amines.

The alpha carbon is the carbon right next to a functional group

Alpha Carbon Acidity

One of the ways to determine the acidity of something is to look at the stability
of it if the hydrogen is removed. So let's look at the stability of a carbon that is
not an alpha carbon with one of its hydrogen atoms removed by a base:
A carbon is typically not very acidic because the resulting carbanion is not very
stable

You notice that there is a negative charge on that carbon. Carbon doesn't
typically like to have a negative charge. It isn't very electronegative, so it
doesn't hold a negative charge as well as other atoms do.

Now let's look at an alpha carbon with a hydrogen removed by a base:

The alpha carbon is more acidic due to the stabilization of resonance structure

There is still a negative charge on that carbon, but there is a second structure
that it can resonate to. Resonance describes electrons' ability to move within
an atom. The reason this helps stabilize the molecule is because the negative
charge is never fully on any one atom:

By looking at the hybrid structure the negative charge is only partially on a

single atom
When looking at the hybrid structure, we see that there is only a partial negative
charge on each of the atoms. In the case of the ketone, the major product will be
with the negative charge on the oxygen. Since oxygen is very electronegative, it
can handle a negative charge. This allows the structure to be stabilized better.
So the alpha carbon is more acidic than a typical carbon.

Alpha Carbon Reactions

Due to the acidity of the alpha carbon, it is able to participate in several
reactions. The general reaction simply takes the electrons from the negative
charge and attacks an electrophile, after which the electrophile gets attached to
the carbon.

The negative charge on the carbon can attack an electrophile creating a

carbon-carbon bond

So really the important part is simply having an electrophile that can react with
the carbon. The electrophile can be a carbonyl, an alkyl halide, or a halogen.

The alkyl halide is the electrophile that the alpha carbon can attack once it has
been deprotonated

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 You are viewing lesson 16 in chapter 5 of the course:

AP Biology: Tutoring Solution

27 chapters | 344 lessons
Ch 1. AP Biology - Science Basics:...
Ch 2. AP Biology - The Origin of Life...
Ch 3. AP Biology - Evolution: Tutoring...
Ch 4. AP Biology - Inorganic Chemistry:...
Ch 5. AP Biology - Organic Chemistry: Tutoring...

 Introduction to Organic Molecules I: Functional Groups 7:26

 Introduction to Organic Molecules II: Monomers and Polymers5:15
 Structure and Function of Carbohydrates7:34
 Structure and Function of Lipids8:23
 Proteins I: Structure and Function6:15
 Proteins III: Structure and Characteristics of the 20 Amino Acids 11:08
 Proteins II: Amino Acids, Polymerization and Peptide Bonds6:11
 Proteins IV: Primary, Secondary, Tertiary and Quaternary Structure 8:55
 Hydroxyl Group: Definition, Structure & Formula2:29
 Pyrimidines: Definition & Examples5:35
 Transport Proteins: Definition, Types, Function & Examples5:31
 Aldol Condensation: Mechanism & Reaction6:10
 Alkaloid Extraction: Definition & Methods
 Alkoxy Group: Definition & Overview
 Alkyl Group: Definition & Overview 4:38
 Alpha Carbon: Acidity & Reactions
 5:32

Next Lesson

Amylopectin: Structure & Function

 Amino Acid Side Chains: Function & Examples 7:15

 What Is an Alkaloid? - Definition & Examples5:22
 Go toAP Biology - Organic Chemistry: Tutoring Solution

Ch 6. AP Biology - Enzymatic...

 Function of Enzymes: Substrate, Active Site & Activation Energy5:20

 Enzyme Activity & Inhibition: Structure, Substrates, pH & Temperature 6:03
  Coenzymes, Cofactors & Prosthetic Groups: Function and Interactions 5:31
 Enzymatic Reactions: Inhibition and Regulation5:41
 Coenzyme: Definition & Examples3:37
 Go toAP Biology - Enzymatic Biochemistry: Tutoring Solution

Ch 7. AP Biology - Cell Biology:...

Ch 8. AP Biology - Requirements of...
Ch 9. AP Biology - Cell Division:...
Ch 10. AP Biology - Metabolic...
Ch 11. AP Biology - DNA and RNA:...
Ch 12. AP Biology - DNA Replication:...
Ch 13. AP Biology - Transcription and...
Ch 14. AP Biology - Genetics and...
Ch 15. AP Biology - Genetic Mutations:...
Ch 16. AP Biology - Phylogeny and the...
Ch 17. AP Biology - Plant Biology:...
Ch 18. AP Biology - Plant Reproduction...
Ch 19. AP Biology - Animal Reproduction...
Ch 20. AP Biology - Anatomy and...
Ch 21. AP Biology - The Circulatory,...
Ch 22. AP Biology - The Nervous, Immune,...
Ch 23. AP Biology - Ecology: Tutoring...
Ch 24. AP Biology - Animal Behavior:...
Ch 25. AP Biology - Basic Molecular...
Ch 26. AP Biology - Laboratory: Tutoring...
Ch 27. AP Biology - Analyzing Scientific...

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