Organic chemistry – The club members >10 million organic compounds!
How to identify them? Name Formula Molecular formula C4H10 Common name ex. aspirin Extended structural formula Systematic name 2-acetyloxybenzoic acid Partially condensed structural formula Condensed structural formula CH3CH2CH2CH3
Molecular representations Compound Chemical Formula Structural formula Line-Angle Drawing Ball-and-stick formula n-butane C4H10 =
Skill Building Converting between different drawing styles : (CH3)2CHOCH2CH3 : Partially condensed structural formula? Extended structural formula? Line angle drawing? (CH3CH2)2CHCH2OCH3 : : : : : Structural formula? : : : : Diazepam
15,000,000 C Largest organic compound in the world
Why so many organic compounds? 1) Long chains … … 2) Multiple bonding possibilities 1 carbon = 4 bonds
Why so many organic compounds? 3) Rings Size Saturation Condensation Heteroatoms
compounds with same number and type of atoms but different structure Why so many organic compounds? compounds with same number and type of atoms but different structure 4) Multiple isomers C4H10 butane n-butane (linear isomer) iso-butane (branched isomer)
Molecular representations Compound Chemical Formula Structural formula Line-Angle Drawing Ball-and-stick formula n-butane C4H10 = iso-butane C4H10 =
Skill Building: Isomers Pentane, C5H12, exists in three isomers. Draw structural formulas for each of them.
Functional Groups
(characteristic properties) Functional Groups Remainder of the molecule (can be anything) Functional group (characteristic properties) A generic carboxylic acid
Some Important Classes of Organic Compounds and Their Functional Groups Functional Group alcohol aldehyde ether ketone carboxylic acid amide ester amine
Your turn: Functional Groups Identify the functional groups in the following compounds: tyroxin
Your turn: Functional Groups Identify the functional groups in the following compounds: adrenalin dopamine
Your Turn. Scientific Practices: Accumulation of Vitamins Look up the structures for vitamins A, C, D, and K. For which vitamins should you watch your dose? Explain your answers. Vitamin A Vitamin C Vitamin K Vitamin D
Stereoisomers Chirality most often results when a carbon atom is bonded to 4 unique groups of atoms.
each highlighted carbon Stereoisomers When an atom (like carbon) forms a tetrahedral center with 4 different groups attached to it, it is called a chirality center Analyze the attachments for each chirality center below each highlighted carbon is bonded to 4 different groups, and is a chirality center
Skill Building: Chiral Molecules Use an asterisk to identify the chiral carbon in these molecules, then draw both chiral isomers using wedge-dash drawings. phenylalanine methamphetamine CH3CH(OH)CH2CH3 2-butanol epinephrine
Rotation of the plane of polarization Polarimeter Light source Unpolarized light Polarizer (fixed) Polarized light Polarimeter tube Rotation of the plane of polarization Analyzer Observer
Time for you to use your nose!
Biological properties of enantiomers Taste Smell D-asparagine L-asparagine S-limonene R-limonene Enantiomers are almost identical… …How can they be so different? 5
Binding model of chiral molecules
Skill Building Examine the structural formulas for naproxen and L-DOPA. For each drug, which is the chiral carbon atom? Identify all of the functional groups present in both drugs. Draw the structural formulas for the mirror images of both molecules. Naproxen L-DOPA