Wilkommen nach Organische Chemie Klasse

ORGANIC-SPEAK IN A NUTSHELL

N-methylphenyl-2-propan-2-amine ????? GOT IT ?

149.2=MW Recognize the Final 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 SYNTHESIS MECHANISM + = 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 1828 pg. 2 of text Friedrich Wohler, boy chemistry wonder becomes Berzelius’s (unpaid) grad student The kid’s big breakthrough… CH 4 N 2 O  CH 4 N 2 O heat NH 4 OCN  (NH 2 ) 2 CO Inorganic salt (ammonium cyanate) Urea (essence of urine) hea t

1835 Vitalism is road kill on the highway of chemistry RIP : VITALISM THEORY OF MATTER

1835 Though 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 ) CH 4 = 25 wt % H + 75 wt % C 2) 1 mole CH 4 = 1 mole C + 2 moles H 2 3) C(s) + 2H 2 (g)  CH 4 (g) kcal/mol CH 4 4) CH 4 (g) + 2O 2 (g)  CO 2 (g) + 2H 2 O(l) -191 Kcal/mol CH 4 5) R(C-H) = 10.9 nm;  (H-C-H)=109.5 o 6) mp= 90 K; bp= 102 K Number heavy

Methane according to organic chemists 2) Bonds are sp 3 hybrids 1)1) 3) Smallest member of alkane family: C n H 2n+2 4) Main source: biological decay 5) Main reaction of CH 4 : Free radical halogen (X) substitution light CH 4 + X 2  CH 3 X + HX

Organic chemists think a lot like…. zoologists 1) What does the animal methane look like ? 2) vertebrate/invertebrate? bonds are sp 3 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: C n H 2n+2

5) What happens when methane meets with other chemical critters ? 5) Main reaction of CH 4 : Free radical halogen (X) substitution light CH 4 + X 2  CH 3 X + 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 O 2 ) 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-NH 2 amines

Extended`phylogeny’ of organic compounds OIL and COAL (dead plants and animals under pressure and low O 2 ) Chain aliphaticsRing aliphaticsaromatics alkanes alkenes alkynes dienes Mono ringsFused rings heterobenzenes phenols benzoates alcohols ketones haloalkenes alkenols napthalenes anthracenes halides ketoesters dione s Bio molecules sugars lipids proteins amines Carboxylic acids DNA Organic-bioorganic divide Biology