Wilkommen nach Organische Chemie Klasse
ORGANIC-SPEAK IN A NUTSHELL
B r2 /w e t C C l4 p cc n ea t
O
Br
A lB r 3 (an h yd .)O
OH8 5 % H 3P O 4
re flu x
OH
S O C l2 (n ea t)N H 3(an h yd .) N aO H NH2
N a B H 4
A l/H g
NH
N-methylphenyl-2-propan-2-amine
NH
????? NH
OH+ OH
GOT IT ?
NH
149.2=MW
Recognize theFinal product ??
Common name: methamphetamine
Pop culture hint
Street name:Crystal meth
1)
2)
3)
Hydride transfer mechanism for Cannizzaro reaction
Got it ?
The Twin Language Skills of Modern Organic Chemistry
1. Synthesis 2. Mechanism
Wilkommen nach Organische Chemie Klasse
SYNTHESISMECHANISM +
= ORGANIC CHEMISTRY
But wait…there’s more !! Breaking Bad :Season 1, episode 1 time 40:51-43:17
GOT IT ?
In the beginning….1828 Vitalism Theory of Matter dominates
1) Matter is divided into organic and inorganic
2) Only living things can create or generate organics
3) Inorganic matter lacks the `essences of life’ = `in vivo’ (of life) quality present in organic matter.
1828 Chemistry is the down-trodden, lower class stepchild of medicine
This tough-looking cookie works for free as the chief chemist of the Stockholm School of Medicine
Johann Jakob Berzelius
A `father’ of modern chemistry
The Big Breakthrough in 1828pg. 2 of text
Friedrich Wohler, boy chemistry wonder becomes Berzelius’s (unpaid) grad student
The kid’s big breakthrough…
CH4N2O CH4N2O
heat
NH4OCN (NH2)2CO
Inorganic salt (ammonium cyanate)
Urea (essence of urine)
heat
1835Vitalism is road kill on the highway of chemistry
RIP : VITALISM THEORY OF MATTER
1835Though vitalism is dead…things are
maybe worse
“Organic chemistry nowadays drives me mad. To me it appears like a primeval tropical forest full o the most remarkable things, a dreadful endless jungle into which one does not dare enter for there seems to be no way out.”Friedrich Wohler (former boy wonder)
1835
Footnote: chemists are still poor vs. doctors but all doctors must take organic chemistry
Methane as described in general chemistry
1) CH4= 25 wt % H + 75 wt % C
2) 1 mole CH4 = 1 mole C + 2 moles H2
3) C(s) + 2H2(g) CH4(g) -17.7 kcal/mol CH4
4) CH4(g) + 2O2(g) CO2(g) + 2H2O(l) -191 Kcal/mol CH4
5) R(C-H) = 10.9 nm; (H-C-H)=109.5o
6) mp= 90 K; bp= 102 K Number heavy
Methane according to organic chemists
2) Bonds are sp3 hybrids
1)
3) Smallest member of alkane family: CnH2n+2
4) Main source: biological decay
5) Main reaction of CH4:Free radical halogen (X) substitution lightCH4 + X2 CH3X + HX
Organic chemists think a lot like…. zoologists
1) What does the animal methane look like ?
2) vertebrate/invertebrate?bonds are sp3 hybrids
4. Where does this methane animal main live???
oil
3) What family of chemical critters does methane belong to ??
Smallest member of alkane family: CnH2n+2
5) What happens when methane meets with other chemical critters ?
5) Main reaction of CH4:Free radical halogen (X) substitution lightCH4 + X2 CH3X + HX
For the mathphobic, Organic is the place to be…
Organic is visual and verbal, not mathematical* (except in advanced courses)
* Except in lab where % yield and mole count rears their nasty heads
More tloc*: organizing the jungle’’more `zoological’ thinking
Thinking Like an Organic Chemist
OIL and COAL (dead plants and animals under pressure and low O2)
Chain aliphatics
Ring aliphatics
aromatics
Alkanes ( )
Alkynes ( )
Alkenes (=)
`functional’ group organizational scheme for organic chemistry
R-H
• R-OH alcohols
• R-X alkyl halides (X=F,Cl,Br,I…)
• R-NH2 amines
Extended`phylogeny’ of organic compounds
OIL and COAL (dead plants and animals under pressure and low O2)
Chain aliphatics Ring aliphatics aromatics
alkanesalkenes alkynes
dienes
Mono rings Fused rings
heterobenzenes
phenols
benzoates
alcohols
ketones
haloalkenes
alkenolsnapthalenes
anthracenes
halides
ketoestersdiones
Bio moleculessugars
lipids proteins
amines
Carboxylic acids
DNAOrganic-bioorganic divide
Biology