Organic chemistry The club members 10 million organic

Organic chemistry – The club members >10 million organic compounds!

How to identify them? Name Common name ex. aspirin Systematic name 2 -acetyloxybenzoic acid Formula Molecular formula C 4 H 10 Extended structural formula Partially condensed structural formula CH 3 CH 2 CH 3

Molecular representations Compound n-butane Chemical Formula Structural formula C 4 H 10 = Line-Angle Drawing Ball-and-stick formula

: : Skill Building Converting between different drawing styles (CH 3)2 CHOCH 2 CH 3 (CH 3 CH 2)2 CHCH 2 OCH 3 Partially condensed structural formula? Extended structural formula? Line angle drawing? : : : Structural formula? : : : Diazepam

15, 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

Why so many organic compounds? 4) Multiple isomers compounds with same number and type of atoms but different structure C 4 H 10 butane n-butane (linear isomer) iso-butane (branched isomer)

Molecular representations Compound n-butane Chemical Formula Structural formula C 4 H 10 = iso-butane C 4 H 10 = Line-Angle Drawing Ball-and-stick formula

Skill Building: Isomers Pentane, C 5 H 12, exists in three isomers. Draw structural formulas for each of them.

Functional Groups

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 ether aldehyde ketone carboxylic acid ester amine amide

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 K Vitamin C Vitamin D

Stereoisomers • Chirality most often results when a carbon atom is bonded to 4 unique groups of atoms.

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 CH 3 CH(OH)CH 2 CH 3 2 -butanol epinephrine

Polarimeter Observer Rotation of the plane of polarization Polarized light Unpolarized light Analyzer Polarimeter tube Polarizer (fixed) Light source

Time for you to use your nose!

Biological properties of enantiomers Taste D-asparagine Smell 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. a. For each drug, which is the chiral carbon atom? b. Identify all of the functional groups present in both drugs. c. Draw the structural formulas for the mirror images of both molecules. Naproxen L-DOPA