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