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

6. 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

7. Molecular representations
Compound
Chemical
Formula
Structural formula
Line-Angle Drawing
Ball-and-stick formula
n-butane
C4H10 =

8. Skill Building Converting between different drawing styles:
(CH3)2CHOCH2CH3 :
Partially condensed structural formula?
Extended structural formula?
Line angle drawing?
(CH3CH2)2CHCH2OCH3 : : : : :
Structural formula? : : : :
Diazepam

9. 15,000,000 C
Largest organic compound in the world

10. Why so many organic compounds?
1) Long chains … …
2) Multiple bonding possibilities
1 carbon = 4 bonds

11. Why so many organic compounds?
3) Rings
Size
Saturation
Condensation
Heteroatoms

12. 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)

13. Molecular representations
Compound
Chemical
Formula
Structural formula
Line-Angle Drawing
Ball-and-stick formula
n-butane
C4H10 =
iso-butane
C4H10 =

14. Skill Building: Isomers
Pentane, C5H12, exists in three isomers. Draw structural formulas for each of them.

15. Functional Groups

16. (characteristic properties)
Functional Groups
Remainder
of the molecule
(can be anything)
Functional
group
(characteristic properties)
A generic carboxylic acid

17. Some Important Classes of Organic Compounds
and Their Functional Groups
Functional Group
alcohol
aldehyde
ether
ketone
carboxylic acid
amide
ester
amine

18. Your turn: Functional Groups
Identify the functional groups in the following compounds:
tyroxin

19. Your turn: Functional Groups
Identify the functional groups in the following compounds:
adrenalin
dopamine

20. 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

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

26. 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

27. 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

28. 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

29. Time for you to use your nose!

31. 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

32. Binding model of chiral molecules

33. 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