1. CHEM 310M: Organic Chemistry in Coke Zero
Professor Julie Geng
Topic Outline:
I. Synthesis/Production of Aspartame
a) Introduction of Aspartame:
i. “Legal name”(IUPAC Name)
ii. Chemical formula and structure
iii. Uses
b) Basic Organic Chemistry
i. Function group: carboxylic acid, alcohol, amine, etc.
ii. Curved arrow and movement of electron pairs
iii. Protection and deprotection
iv. Esterification (carboxylic acid and alcohol)
c) Components of Aspartame: Amino Acids (aspartic acid and phenylalanine)
and Alcohol (methanol)
i. Amino acids (Proteins) and types of amino acids
ii. Definition of carboxylic acid
iii. Definition of alcohol (methanol)
d) Esterification (mechanism) [example of aspartame]  Poster
i. Purpose of a mechanism
ii. Resonance structure and stability: delocalized electrons
iii. Tetrahedral Intermediate
e) Peptide Bond(mechanism) [example of aspartame] Poster
i. Definition of a peptide bond
f) L and D isomers in amino acid[OPTIONAL]
i. Chirality
ii. Stereoisomers
iii. Left-handedness and right-handedness
g) Acid Base Chemistry of Amino Acid [OPTIONAL]
i. Zwitterion
ii. Isoelectronic point
iii. Titration curve (Henderson-Hassel Bach Rule)
iv. Amphoteric behavior

2. II. Health concerns of aspartame
a) Physical
b) Mental
Key Terms:
1. R-Group: an abbreviation for any group in which a carbon or hydrogen atom is
attacked to the rest of the molecule
2. Carboxylic acid group: an organic function group consisting of a carbon atom double
bonded to an oxygen atom and single bonded to a hydroxyl group; commonly written
as –COOH
3. Alcohol:substance containing an –OH group attached to a hydrocarbon group
4. Function group: a specific group of atoms within a molecule that is responsible for
characteristic chemical reactions of that molecule
5. Amino group: an –NH2 group; organic compounds which have this groups are called
amines
6. Ester: an organic compound where the hydrogen in the compound’s carboxyl group is
replaced with a hydrocarbon group
7. Amine: a compound in which one or more of the hydrogen atoms in ammonia have
been replaced by an organic functional group
8. Amide: a functional group containing a carbonyl group linked to a nitrogen atom
9. Carbonyl: the carbonyl function group is a divalent group consisting of a carbon atom
with a double-bond to oxygen
10. Alpha carbon: a carbon atom bonded to a functional group in an organic compound
11. Amino Acids:
a) The molecular building blocks of proteins
b) Contain a carboxylic acid group and an amino group on the alpha carbon
c) Ionized in solution
d) Each contain a different side group (R)
12. Types of Amino Acids:
a) Nonpolar (hydrophobic) with hydrocarbon side chains
b) Polar (hydrophilic) with polar or ionic side chains:
i. Acidic: with acidic side chains (R group is a carboxylic acid)
ii. Basic: with –NH2 side chains
13. Peptide Bond:
a) An amide bond
b) Forms between the carboxyl group of one amino acid and the amino group of the
next amino acid
14. Tetrahedral Intermediate: a reaction intermediate in which the bond arrangement
around an initially double-bonded carbon atom has been transformed from trigonal to
tetrahedral